Journal articles: 'Chalcones'

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Olender, Dorota, Anna Pawełczyk, Anna Leśków, Katarzyna Sowa-Kasprzak, Lucjusz Zaprutko, and Dorota Diakowska. "Synthesis of bis-Chalcones Based on Green Chemistry Strategies and Their Cytotoxicity Toward Human MeWo and A375 Melanoma Cell Lines." Molecules 29, no. 21 (October 31, 2024): 5171. http://dx.doi.org/10.3390/molecules29215171.

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Chalcone is an aromatic ketone that forms the central core of many important biological compounds. Chalcone derivatives show various biological activities, especially anti-inflammatory, antibacterial, antioxidant, and anticancer activities, and also inhibit melanoma cell growth. In this study, we synthesized chalcone compounds with bis-chalcone’s chemical structure under microwave (MW) and microwave–ultrasound (MW-US) conditions and compared them to chalcones produced using the classical synthesis method. All bis-chalcones were synthesized with terephthalaldehyde and an appropriate aromatic ketone as substrates in Claisen–Schmidt condensation. All the obtained compounds were tested regarding their roles as potential anticancer agents. The cytotoxic effect of the bis-chalcones against human MeWo and A375 melanoma cell lines was investigated through colorimetric MTT and SRB assays. The data were analyzed statistically. In the case of the synthesis of bis-chalcones, it was determined that the use of green conditions supported by the MW or MW-US factors led to an increase in the yield of the final products and a reduction in the reaction time compared to the classic method. The biological results showed the high cytotoxic effect of bis-chalcones. The present results show the compounds’ high antiproliferative and cytotoxic potential, especially for the two selected bis-chalcone derivatives (3b and 3c), in particular, at concentrations of 50 μM–200 μM at 24, 48 h, and 72 h of incubation. The use of MW and US for the synthesis of bis-chalcones significantly improved the process compared to the classical method. The derivatives containing two hydroxy and two methoxy groups were the most effective against the tested cancer cells.

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Georgiou, Nikitas, Andromachi Tzani, Kyriaki Vavougyiou, Christos Papadopoulos, Nikolaos Eleftheriadis, Primož Šket, Demeter Tzeli, Tuomas Niemi-Aro, Anastasia Detsi, and Thomas Mavromoustakos. "Synthesis of Anti-Inflammatory Drugs’ Chalcone Derivatives and a Study of Their Conformational Properties Through a Combination of Nuclear Magnetic Resonance Spectroscopy and Molecular Modeling." Pharmaceuticals 18, no. 1 (January 13, 2025): 88. https://doi.org/10.3390/ph18010088.

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Background: In this study, two chalcone analogs were synthesized through in silico and experimental methods, and their potential to inhibit the lipoxygenase enzyme, which plays a role in the inflammation pathway, was assessed. Specifically, this study is a continuation of previous research in which chalcone derivatives were synthesized and characterized. Objectives/Methods: In the current work, we present the re-synthesis of two chalcones, with a focus on their docking studies, NMR analysis, and dynamic simulations. The structure of each chalcone was elucidated through a combination of Nuclear Magnetic Resonance (NMR) and Density Functional Theory (DFT). The substituent effect on the absorption spectrum of the two chalcone derivatives was studied. Results: A “LOX–chalcone” complex, predicted by docking studies, was further examined using molecular dynamics (MD) simulations to evaluate the stability of the complex. After fully characterizing the “LOX–chalcone” complexes in silico, the atomic details of each chalcone’s interaction with LOX-1 and 5-LOX were revealed through Saturation Transfer Difference (STD) NMR (Nuclear Magnetic Resonance). Finally, their selectivity profile was investigated against human 15-LOX-1 and general Lipoxidase activity. Conclusions: The in silico methods suggest that chalcones could be promising lead compounds for drug designs targeting the LOX enzyme.

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Rudrapal, Mithun, Johra Khan, Abdul Aziz Bin Dukhyil, Randa Mohammed Ibrahim Ismail Alarousy, Emmanuel Ifeanyi Attah, Tripti Sharma, Shubham Jagdish Khairnar, and Atul Rupchand Bendale. "Chalcone Scaffolds, Bioprecursors of Flavonoids: Chemistry, Bioactivities, and Pharmacokinetics." Molecules 26, no. 23 (November 26, 2021): 7177. http://dx.doi.org/10.3390/molecules26237177.

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Chalcones are secondary metabolites belonging to the flavonoid (C6-C3-C6 system) family that are ubiquitous in edible and medicinal plants, and they are bioprecursors of plant flavonoids. Chalcones and their natural derivatives are important intermediates of the flavonoid biosynthetic pathway. Plants containing chalcones have been used in traditional medicines since antiquity. Chalcones are basically α,β-unsaturated ketones that exert great diversity in pharmacological activities such as antioxidant, anticancer, antimicrobial, antiviral, antitubercular, antiplasmodial, antileishmanial, immunosuppressive, anti-inflammatory, and so on. This review provides an insight into the chemistry, biosynthesis, and occurrence of chalcones from natural sources, particularly dietary and medicinal plants. Furthermore, the pharmacological, pharmacokinetics, and toxicological aspects of naturally occurring chalcone derivatives are also discussed herein. In view of having tremendous pharmacological potential, chalcone scaffolds/chalcone derivatives and bioflavonoids after subtle chemical modification could serve as a reliable platform for natural products-based drug discovery toward promising drug lead molecules/drug candidates.

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Chen, Jie, Chen-Fu Liu, and Guo-Wu Rao. "Progress in the Synthesis, Angiogenesis Activity and Mechanism of Chalcone Derivatives." Mini-Reviews in Organic Chemistry 17, no. 7 (October 9, 2020): 814–27. http://dx.doi.org/10.2174/1570193x17666191223161941.

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Cancer is a common disease that poses a serious threat to human health. Angiogenesis is essential for the growth and metabolism of tumors, providing oxygen and nutrition for the growth of cells and tissues. However, angiogenesis of tumors depends on the stimulation of growth factors. Vascular Endothelial Growth Factor (VEGFR) is the most unique factor. Therefore, VEGF/VEGFR targeting anticancer drugs are playing an increasingly significant role in clinical trials. In addition, it has been proved that chalcone, the precursor of natural flavonoids, has potential anti-tumor activity, especially anti-angiogenesis activity. This review summarizes the reports about the anti-angiogenesis of chalcone derivatives. Based on the chalcone skeleton, it is divided into substituted chalcones and modified chalcones. The anti-angiogenesis activities of natural or synthetic chalcones, benzene ring modified or connecting bridge modified chalcones are described in this review.

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George, Ginson, Vishal Payyalot Koyiparambath, Sunitha Sukumaran, Aathira Sujathan Nair, Leena K. Pappachan, Abdullah G. Al-Sehemi, Hoon Kim, and Bijo Mathew. "Structural Modifications on Chalcone Framework for Developing New Class of Cholinesterase Inhibitors." International Journal of Molecular Sciences 23, no. 6 (March 14, 2022): 3121. http://dx.doi.org/10.3390/ijms23063121.

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Due to the multifaceted pharmacological activities of chalcones, these scaffolds have been considered one of the most privileged frameworks in the drug discovery process. Structurally, chalcones are α, β-unsaturated carbonyl functionalities with two aryl or heteroaryl units. Amongst the numerous pharmacological activities explored for chalcone derivatives, the development of novel chalcone analogs for the treatment of Alzheimer’s disease (AD) is among the research topics of most interest. Chalcones possess numerous advantages, such as smaller molecular size, opportunities for further structural modification thereby altering the physicochemical properties, cost-effectiveness, and convenient synthetic methodology. The present review highlights the recent evidence of chalcones as a privileged structure in AD drug development processes. Different classes of chalcone-derived analogs are summarized for the easy understanding of the previously reported analogs as well as the importance of certain functionalities in exhibiting cholinesterase inhibition. In this way, this review will shed light on the medicinal chemistry fraternity for the design and development of novel promising chalcone candidates for the treatment of AD.

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Jasim, Hiba A., Lutfun Nahar, Mohammad A. Jasim, Sharon A. Moore, Kenneth J. Ritchie, and Satyajit D. Sarker. "Chalcones: Synthetic Chemistry Follows Where Nature Leads." Biomolecules 11, no. 8 (August 13, 2021): 1203. http://dx.doi.org/10.3390/biom11081203.

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Chalcones belong to the flavonoid class of phenolic compounds. They form one of the largest groups of bioactive natural products. The potential anticancer, anti-inflammatory, antimicrobial, antioxidant, and antiparasitic properties of naturally occurring chalcones, and their unique chemical structural features inspired the synthesis of numerous chalcone derivatives. In fact, structural features of chalcones are easy to construct from simple aromatic compounds, and it is convenient to perform structural modifications to generate functionalized chalcone derivatives. Many of these synthetic analogs were shown to possess similar bioactivities as their natural counterparts, but often with an enhanced potency and reduced toxicity. This review article aims to demonstrate how bioinspired synthesis of chalcone derivatives can potentially introduce a new chemical space for exploitation for new drug discovery, justifying the title of this article. However, the focus remains on critical appraisal of synthesized chalcones and their derivatives for their bioactivities, linking to their interactions at the biomolecular level where appropriate, and revealing their possible mechanisms of action.

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Dhaliwal, Jagjit Singh, Said Moshawih, Khang Wen Goh, Mei Jun Loy, Md Sanower Hossain, Andi Hermansyah, Vijay Kotra, et al. "Pharmacotherapeutics Applications and Chemistry of Chalcone Derivatives." Molecules 27, no. 20 (October 19, 2022): 7062. http://dx.doi.org/10.3390/molecules27207062.

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Chalcones have been well examined in the extant literature and demonstrated antibacterial, antifungal, anti-inflammatory, and anticancer properties. A detailed evaluation of the purported health benefits of chalcone and its derivatives, including molecular mechanisms of pharmacological activities, can be further explored. Therefore, this review aimed to describe the main characteristics of chalcone and its derivatives, including their method synthesis and pharmacotherapeutics applications with molecular mechanisms. The presence of the reactive α,β-unsaturated system in the chalcone’s rings showed different potential pharmacological properties, including inhibitory activity on enzymes, anticancer, anti-inflammatory, antibacterial, antifungal, antimalarial, antiprotozoal, and anti-filarial activity. Changing the structure by adding substituent groups to the aromatic ring can increase potency, reduce toxicity, and broaden pharmacological action. This report also summarized the potential health benefits of chalcone derivatives, particularly antimicrobial activity. We found that several chalcone compounds can inhibit diverse targets of antibiotic-resistance development pathways; therefore, they overcome resistance, and bacteria become susceptible to antibacterial compounds. A few chalcone compounds were more active than conventional antibiotics, like vancomycin and tetracycline. On another note, a series of pyran-fused chalcones and trichalcones can block the NF-B signaling complement system implicated in inflammation, and several compounds demonstrated more potent lipoxygenase inhibition than NSAIDs, such as indomethacin. This report integrated discussion from the domains of medicinal chemistry, organic synthesis, and diverse pharmacological applications, particularly for the development of new anti-infective agents that could be a useful reference for pharmaceutical scientists.

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Ouyang, Yang, Juanjuan Li, Xinyue Chen, Xiaoyu Fu, Si Sun, and Qi Wu. "Chalcone Derivatives: Role in Anticancer Therapy." Biomolecules 11, no. 6 (June 16, 2021): 894. http://dx.doi.org/10.3390/biom11060894.

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Chalcones (1,3-diaryl-2-propen-1-ones) are precursors for flavonoids and isoflavonoids, which are common simple chemical scaffolds found in many naturally occurring compounds. Many chalcone derivatives were also prepared due to their convenient synthesis. Chalcones as weandhetic analogues have attracted much interest due to their broad biological activities with clinical potentials against various diseases, particularly for antitumor activity. The chalcone family has demonstrated potential in vitro and in vivo activity against cancers via multiple mechanisms, including cell cycle disruption, autophagy regulation, apoptosis induction, and immunomodulatory and inflammatory mediators. It represents a promising strategy to develop chalcones as novel anticancer agents. In addition, the combination of chalcones and other therapies is expected to be an effective way to improve anticancer therapeutic efficacy. However, despite the encouraging results for their response to cancers observed in clinical studies, a full description of toxicity is required for their clinical use as safe drugs for the treatment of cancer. In this review, we will summarize the recent advances of the chalcone family as potential anticancer agents and the mechanisms of action. Besides, future applications and scope of the chalcone family toward the treatment and prevention of cancer are brought out.

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Rezende-Júnior, Luís Mário, Leila Maria de Sousa Andrade, Antonio Linkoln Alves Borges Leal, Avilnete Belem de Souza Mesquita, Ana Lurdes Portela de Araújo dos Santos, José de Sousa Lima Neto, José Pinto Siqueira-Júnior, et al. "Chalcones Isolated from Arrabidaea brachypoda Flowers as Inhibitors of NorA and MepA Multidrug Efflux Pumps of Staphylococcus aureus." Antibiotics 9, no. 6 (June 20, 2020): 351. http://dx.doi.org/10.3390/antibiotics9060351.

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Bacterial resistance to antibiotics has become a public health issue around the world. The present study aimed to evaluate the antibacterial activity of chalcones isolated from flowers of Arrabidaea brachypoda, and their potential as efflux pump inhibitors of Staphylococcus aureus efflux pumps. Microdilution assays were performed with natural products from A. brachypoda. Chalcones 1, 3, 4, and 5 did not show intrinsic antimicrobial activity against all S. aureus strains tested, but they were able to potentiate the Norfloxacin action against the SA1199-B (norA) strain, with a better modulating action for the 4 trimethoxylated chalcone. All chalcones were also able to potentiate the action of EtBr against SA1199-B strain, suggesting a potential NorA inhibition. Moreover, chalcone 4 was able to interfere in the activity of MepA, and interfered weakly in the QacA/B activity. Molecular docking analyzes showed that tested chalcones are capable of binding in the hydrophobic cavity of NorA and MepA, in the same Norfloxacin binding site, indicating that chalcone 4 compete with the antibiotic for the same NorA and MepA binding sites. Association of chalcone 4 with Norfloxacin could be an alternative against multidrug resistant S. aureus over-productive of NorA or MepA.

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Tantawy, Mohamed A., Farid M. Sroor, Magda F. Mohamed, Mostafa E. El-Naggar, Fatma M. Saleh, Hamdi M. Hassaneen, and Ismail A. Abdelhamid. "Molecular Docking Study, Cytotoxicity, Cell Cycle Arrest and Apoptotic Induction of Novel Chalcones Incorporating Thiadiazolyl Isoquinoline in Cervical Cancer." Anti-Cancer Agents in Medicinal Chemistry 20, no. 1 (April 10, 2020): 70–83. http://dx.doi.org/10.2174/1871520619666191024121116.

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Background: Chalcones are naturally occurring compounds found in various plant species which are widely used for the traditional popular treatments. Chalcones are distinguished secondary metabolites that are reported to display diverse biological activities such as antiviral, antiplatelet, anti-inflammatory, anticancer, antibacterial and antioxidant agents. The presence of a,ß-unsaturated carbonyl group in chalcones is assumed to be responsible for their bioactivity. In addition, heterocyclic compounds having nitrogen such as isoquinolines are of considerable interest as they constitute the core structural element of many alkaloids that have enormous pharmacological activities. Objective: The objective of this study is the synthesis and biological activity of novel chalcones incorporating thiadiazolyl isoquinoline as potential anticancer candidates. Different genetic tools were used in an attempt to know the mechanism of action of this compound against breast cancer. Methods: An efficient one pot synthesis of novel chalcones incorporating thiadiazolyl isoquinoline has been developed. The cytotoxic activity of the novel synthesized compounds was performed against four different kinds of cancer cell lines. Results: Among all the tested derivatives, chalcone 3 has the best cytotoxic profile against A549, MCF7, and HeLa cell lines, with IC50s (66.1, 51.3, and 85.1μM, respectively). Molecular docking studies for chalcone 3 revealed that CDK2, and EGFRTK domains have strong binding affinities toward the novel chalcone 3, while tubulin-colchicine-ustiloxin, and VEGFRTK domains illustrated moderate mode of binding. Conclusion: We have developed an efficient method for the synthesis of novel chalcones incorporating thiadiazolyl isoquinoline. All compounds showed better cytotoxicity results against four kinds of cancer cell lines (A549, MCF7, HCT116, and HELA cells). The results depicted that chalcone 3 has a high and promising cytotoxic effect against HELA cell line and the mechanism of cytotoxicity was widely studied through different theoretical and experimental tools. Thus, the newly synthesized derivative 3 can be utilized as a novel chemotherapeutic compound for cervical carcinoma.

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Giacomello, Thaís F., Gunar V. da S. Mota, Antônio M. de J. C. Neto, and Fabio L. P. Costa. "Use of Replaced Chalcones to Generate a 13C Chemical Shift Staging Factor for Chalcone and Its Derivate." Advanced Science, Engineering and Medicine 12, no. 4 (April 1, 2020): 464–72. http://dx.doi.org/10.1166/asem.2020.2548.

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Chalcones have attracted the attention of researchers for decades, they are biologically classified as secondary metabolites of low molecular weight. These are considered as the precursors of flavonoids and they are widely distributed in plants such as vegetables, fruits, teas and spices. It has been demonstrating that chalcones possess many important bioactivities including properties of antioxidants and other evidence of its potential beneficial effects on health. Chalcone compounds and its derivatives have been showing a growing interest in the therapeutic properties. Nuclear magnetic resonance (NMR) spectroscopy is one of the most important tools for determining the structures of organic molecules. In the work present a 13C Nuclear magnetic resonance chemical shift protocol of chalcones and derivative based on the application of scaling factor with chalcone molecules. This protocol consists of using density functional theory with gauge-including atomic orbital method to calculating 13C chemical shifts and the application of a parameterized scaling factor in order to ensure accurate structural determination of chalcones and derivative.

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Haryadi, Winarto, and Harno Dwi Pranowo. "Molecular docking and dynamics analysis of halogenated imidazole chalcone as anticancer compounds." Pharmacia 70, no. 2 (May 22, 2023): 323–29. http://dx.doi.org/10.3897/pharmacia.70.e101989.

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Cancer is one of the three biggest causes of death in the world. The development of new drugs against this disease is a serious study that must be carried out in order to reduce mortality and extend the life span of sufferers. The aim of this research was to develop a new anti-cancer drug based on halogenated imidazole chalcones have been conducted. A 18 The halogenated imidazole chalcone compound was designed and performed molecular docking. Potential compounds of molecular docking are then carried out molecular dynamics. The results of molecular docking show that the potential chalcones based on bond affinity and specific interactions are chalcones B5, B6, C5, and C6. Analysis of the molecular dynamics result parameters are root mean standard deviation (RMSD) complex, root mean square fluctuation (RMSF), Radius of Gyration, Protein-ligand hydrogen bonding, and complex stability with generalized born surface area (GBSA) method, where the potential chalcone compounds are chalcones B5 and B6.

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Dwivedi, Pratibha, and Dr Alka Pradhan. "Synthesis and Characterization of Various Pyrazolines From Chalcones." International Journal for Research in Applied Science and Engineering Technology 10, no. 5 (May 31, 2022): 2108–10. http://dx.doi.org/10.22214/ijraset.2022.42656.

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Abstract: Some novel series of pyrazoline derivatives were synthesized from Chalcones. Various Pyrazoline derivatives were prepared by reflux reaction of Chalcone with Phenyl Hydrazine Hydrate in ethanolic solution. The structures of the newly synthesized Pyrazoline derivatives have been characterized by spectral data. Keywords: Pyrazolines, chalcones, spectral analysis.

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Silva, Priscila Teixeira da, Thiago Sampaio de Freitas, Diniz Maciel Sena, Paulo Nogueira Bandeira, Murilo Ségio da Silva Julião, Emmanuel Silva Marinho, Ana Aline Coêlho Alcanfor, et al. "Structural, Vibrational and Electrochemical Analysis and Antibacterial Potential of Isomeric Chalcones Derived from Natural Acetophenone." Applied Sciences 10, no. 14 (July 8, 2020): 4713. http://dx.doi.org/10.3390/app10144713.

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Background: Chalcones are part of a family of small phenolic compounds that are being extensively studied for presenting a diversity of molecular structures and biological activities. In this paper, two chalcones, (E)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one (1), (E)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one (2), were synthesized by Claisen–Schmidt condensation. Methods: The molecular structures of these chalcones were determined by Nuclear Magnetic Resonance and characterized by infrared, Raman spectroscopy, and electrochemical analysis at room temperature. Vibrational wavenumbers were predicted using Functional Density Theory (DFT) calculations, and their normal modes were analyzed in terms of potential energy distribution (PED). Besides this, DFT calculations were performed to obtain the molecular orbitals and their quantum descriptors. The UV-Vis absorption spectrum of the synthesized chalcones was measured and compared with each other. In addition, analyses of antimicrobial activity and modulation of antibiotic resistance were carried out to assess the antibacterial potential of these chalcones. Results: The vibrational spectra of polycrystalline chalcones obtained by ATR-FTIR, FT-Raman and DFT calculations allowed a complete assignment of the vibrational modes, and revealed the quantum chemical parameters. Both chalcones did not show good responses when associated with the antibiotics Ciprofloxacin and Cephalexin against S. aureus 10 and E. coli 06 strains. However, a significant potentiating of the Gentamicin activity against S. aureus 10 and E. col 06 strains was observed for chalcone 2. On the other hand, when associated with Norfloxacin, an antagonistic effect was observed. The results found for EtBr suggest that, although the tested chalcones behave as efflux pump inhibitors, probably inhibiting other efflux pumps, they were not able to inhibit NorA. Thus, these synthetic chalcones are not recommended for use in association with Norfloxacin against strains of S. aureus 1199-B that overexpress the NorA gene. Conclusions: Spectroscopic data confirmed the structure of the chalcones, and chalcone 2 showed potential as an adjuvant in antibiotic therapy.

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Liargkova, Thalia, Nikolaos Eleftheriadis, Frank Dekker, Efstathia Voulgari, Constantinos Avgoustakis, Marina Sagnou, Barbara Mavroidi, Maria Pelecanou, and Dimitra Hadjipavlou-Litina. "Small Multitarget Molecules Incorporating the Enone Moiety." Molecules 24, no. 1 (January 7, 2019): 199. http://dx.doi.org/10.3390/molecules24010199.

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Chalcones represent a class of small drug/druglike molecules with different and multitarget biological activities. Small multi-target drugs have attracted considerable interest in the last decade due their advantages in the treatment of complex and multifactorial diseases, since “one drug-one target” therapies have failed in many cases to demonstrate clinical efficacy. In this context, we designed and synthesized potential new small multi-target agents with lipoxygenase (LOX), acetyl cholinesterase (AChE) and lipid peroxidation inhibitory activities, as well as antioxidant activity based on 2-/4- hydroxy-chalcones and the bis-etherified bis-chalcone skeleton. Furthermore, the synthesized molecules were evaluated for their cytotoxicity. Simple chalcone b4 presents significant inhibitory activity against the 15-human LOX with an IC50 value 9.5 µM, interesting anti-AChE activity, and anti-lipid peroxidation behavior. Bis-etherified chalcone c12 is the most potent inhibitor of AChE within the bis-etherified bis-chalcones followed by c11. Bis-chalcones c11 and c12 were found to combine anti-LOX, anti-AchE, and anti-lipid peroxidation activities. It seems that the anti-lipid peroxidation activity supports the anti-LOX activity for the significantly active bis-chalcones. Our circular dichroism (CD) study identified two structures capable of interfering with the aggregation process of Aβ. Compounds c2 and c4 display additional protective actions against Alzheimer’s disease (AD) and add to the pleiotropic profile of the chalcone derivatives. Predicted results indicate that the majority of the compounds with the exception of c11 (144 Å) can cross the Blood Brain Barrier (BBB) and act in CNS. The results led us to propose new leads and to conclude that the presence of a double enone group supports better biological activities.

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Krajka-Kuźniak, Violetta, Marta Belka, and Katarzyna Papierska. "Targeting STAT3 and NF-κB Signaling Pathways in Cancer Prevention and Treatment: The Role of Chalcones." Cancers 16, no. 6 (March 8, 2024): 1092. http://dx.doi.org/10.3390/cancers16061092.

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Chalcones are a type of natural flavonoid compound that have been found to possess promising anticancer properties. Studies have shown that chalcones can inhibit the growth and proliferation of cancer cells, induce apoptosis, and suppress tumor angiogenesis. In addition to their potential therapeutic applications, chalcones have also been studied for their chemopreventive effects, which involve reducing the risk of cancer development in healthy individuals. Overall, the anticancer properties of chalcones make them a promising area of research for developing new cancer treatments and preventative strategies. This review aims to provide a thorough overview of the central studies reported in the literature concerning cancer prevention and the treatment of chalcones. Although chalcones target many different mechanisms, the STAT and NF-κB signaling pathways are the ones this review will focus on, highlighting the existing crosstalk between these two pathways and considering the potential therapeutic opportunities for chalcone combinations.

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Nashwa K.K and K. Anuja. "Chalcones As Modulators Of Neurodegenerative Processes: Exploring Their Role In Alzheimer's And Parkinson's Diseases." International Journal of Allied Medical Sciences and Clinical Research 12, no. 3 (August 17, 2024): 340–53. https://doi.org/10.61096/ijamscr.v12.iss3.2024.340-353.

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Neurodegenerative diseases such as Alzheimer's and Parkinson's present a significant global health challenge due to their increasing prevalence and the lack of effective treatments. Chalcones, a class of natural flavonoids, have emerged as promising therapeutic agents due to their diverse biological activities, including antioxidant, anti-inflammatory, and enzyme inhibitory properties. This review comprehensively examines the role of chalcones as modulators of neurodegenerative processes, focusing on their potential therapeutic applications in Alzheimer's and Parkinson's diseases. We explore the molecular mechanisms underlying chalcone activity, including the inhibition of key enzymes like monoamine oxidases (MAOs) and acetylcholinesterase (AChE), as well as their impact on amyloid-beta aggregation, tau phosphorylation, and neuroinflammation. Additionally, we highlight recent advances in structure–activity relationship (SAR) studies that have led to the development of potent chalcone derivatives with enhanced neuroprotective properties. We also discusses the therapeutic potential and limitations of chalcones, providing insights into future research directions for the development of chalcone-based treatments for neurodegenerative diseases.

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Sweeting, Stephen G., Charlie L. Hall, Jason Potticary, Natalie E. Pridmore, Stephen D. Warren, Matthew E. Cremeens, Gemma D. D'Ambruoso, Masaomi Matsumoto, and Simon R. Hall. "The solubility and stability of heterocyclic chalcones compared with trans-chalcone." Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials 76, no. 1 (February 1, 2020): 13–17. http://dx.doi.org/10.1107/s2052520619015907.

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Heterocyclic chalcones are a recently explored subgroup of chalcones that have sparked interest due to their significant antibacterial and antifungal capabilities. Herein, the structure and solubility of two such compounds, (E)-1-(1H-pyrrol-2-yl)-3-(thiophen-2-yl)prop-2-en-1-one and (E)-3-phenyl-1-(1H-pyrrol-2-yl)prop-2-en-1-one, are assessed. Single crystals of (E)-1-(1H-pyrrol-2-yl)-3-(thiophen-2-yl)prop-2-en-1-one were grown, allowing structural comparisons between the heterocyclic chalcones and (2E)-1,3-diphenylprop-2-en-1-one, trivially known as trans-chalcone. The two heterocyclic chalcones were found to be less soluble in all solvents tested and to have higher melting points than trans-chalcone, probably due to their stronger intermolecular interactions arising from the functionalized rings. Interestingly, however, it was found that the addition of the thiophene ring in (E)-1-(1H-pyrrol-2-yl)-3-(thiophen-2-yl)prop-2-en-1-one increased both the melting point and solubility of the sample compared with (E)-3-phenyl-1-(1H-pyrrol-2-yl)prop-2-en-1-one. This observation may be key for the future crystal engineering of heterocyclic chalcones for pharmaceutical applications.

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K. Saini, K. Rajendra, S. Amit Choudhary, Yogesh C. Joshi, and P. Joshi. "Solvent Free Synthesis of Chalcones and their Antibacterial Activities." E-Journal of Chemistry 2, no. 4 (2005): 224–27. http://dx.doi.org/10.1155/2005/294094.

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The solvent free synthesis of six chalcones was carried out by grinding the piperanal and the acetophenone (unsubstituted, 4-methyl, 4-methoxy, 4-bromo, 4-nitro, 3-chloro) in the presence of solid sodium hydroxide with a mortar and pestle. In general, the chalcones were obtained in high yield and high purity. Minor quantities of Ketol and Michael addition product were easily removed by recrystallization. The result indicates a correlation between the success of the solvent-free synthesis and melting point of the chalcone. Chalcone with relatively high melting points (higher than 80°C) were obtained in high yields. The two chalcones that could not be produced in good yields were having relatively low melting points. They have been screened for their antibacterial activity against Gram positive and Gram negative bacteria.

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Mulyana, Fathoni Ega, Stephanus Satria Wira Waskitha, Deni Pranowo, Melati Khairuddean, and Tutik Dwi Wahyumingsih. "Synthesis of chalcone derivatives with methoxybenzene and pyridine moieties as potential antimalarial agents." Pharmacia 70, no. 4 (November 7, 2023): 1305–13. http://dx.doi.org/10.3897/pharmacia.70.e107406.

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Malaria remains an endemic disease in tropical regions, urgently needed the search for effective antimalarial agents due to resistance against existing drugs. This study investigated the potential antimalarial activity of pyridine-based chalcone derivatives against P. falciparum 3D7 and FCR3 strains. The chalcones were synthesized through a one-pot method using various pyridine carbaldehyde, resulting in yields ranging from 53.74 to 86.37%, and all products were characterized using FTIR, GC-MS, and NMR spectroscopies. Among the six chalcones tested, chalcone A [1-(2-methoxyphenyl)-3-(pyridin-2-yl)prop-2-en-1-one] displayed the highest antimalarial activity with IC50 values of 0.48 and 0.31 μg/mL against P. falciparum 3D7 and FCR3 strains, respectively, and a resistance index of 0.65. Molecular docking studies highlighted the interaction of the carbonyl group of all chalcones with Asn108 amino acid residue in the PfDHFR-TS active site via hydrogen bonding, demonstrating their potential as the antimalarial agent. Notably, the positioning of methoxy and pyridine substituents significantly influenced the antimalarial activity of the chalcones.

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Mustikasari, Kamilia, and Uripto Trisno Santoso. "The Benefits of Chalcone and Its Derivatives as Antibacterial Agents: A Review." BIO Web of Conferences 20 (2020): 03007. http://dx.doi.org/10.1051/bioconf/20202003007.

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Chalcone is a secondary metabolite compound found in plants. Chalcones contain two aryl rings, namely ring A and B which connected to the α,β unsaturated ketones. Chalcone derivatives are synthesized by various substituent groups in both rings, as well as the types of rings. These variations make chalcone and its derivatives, have interesting bioactivity, one of which is antibacterial. This review is considered the chalcone-derived compounds that have antibacterial bioactivity, including methoxy, hydroxy, prenyl, and halogen groups in ring A or B. Besides, there are two forms of these rings as well such as pyrroly l-furany l-chalcones and indoly l-thiopheny l-chalcone. We hope this review is useful for the development of the synthesis of organic compounds and the discovery of new drug design.

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Wang, Danni, Jing Liang, Jing Zhang, Yuefei Wang, and Xin Chai. "Natural Chalcones in Chinese Materia Medica: Licorice." Evidence-Based Complementary and Alternative Medicine 2020 (March 16, 2020): 1–14. http://dx.doi.org/10.1155/2020/3821248.

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Licorice is an important Chinese materia medica frequently used in clinical practice, which contains more than 20 triterpenoids and 300 flavonoids. Chalcone, one of the major classes of flavonoid, has a variety of biological activities and is widely distributed in nature. To date, about 42 chalcones have been isolated and identified from licorice. These chalcones play a pivotal role when licorice exerts its pharmacological effects. According to the research reports, these compounds have a wide range of biological activities, containing anticancer, anti-inflammatory, antimicrobial, antioxidative, antiviral, antidiabetic, antidepressive, hepatoprotective activities, and so on. This review aims to summarize structures and biological activities of chalcones from licorice. We hope that this work can provide a theoretical basis for the further studies of chalcones from licorice.

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Desai, Dr Arpitaben P., and Patel Drashti K. "Synthesis of Chalcone Derivatives and its Antimicrobial Activities." INTERANTIONAL JOURNAL OF SCIENTIFIC RESEARCH IN ENGINEERING AND MANAGEMENT 07, no. 11 (November 1, 2023): 1–11. http://dx.doi.org/10.55041/ijsrem27306.

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To investigate the in vitro antibacterial activity of these chalcones against Gram-positive and Gram- negative bacteria as well as fungi, a series of five chalcones that closely mimic those found in nature were created. By the Claisen-Schmidt condensation and a green chemistry procedure that used sodium hydroxide as a catalyst in clean water, chalcones were produced from acetophenone and substituted benzaldehydes with good yields. Amoxicillin and fluconazole were used as standards for the antimicrobial assessment, which was done using the filter paper disc plate technique on a set of chosen bacteria. The structure of the generated derivatives has been determined by employing FTIR Spectroscopy, NMR, and other physicochemical characteristics. These synthesized chalcones showed the expected antibacterial action after being tested for it. This green procedure is the most practical, effective, and environmentally friendly method for the synthesis of chalcones by the Claisen- Schmidt condensation because it is simple to synthesize and purify these chalcones and because high yields are observed. The future development of chalcone derivatives as commercial antibacterial medicines is quite promising.

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Sinha, Reema, Pankaj Kumar, and Ashish Sikdar. "A COMPREHENSIVE REVIEW ON CHALCONE ANALOGUES-VERSATILE SCAFFOLD WITH MEDICINAL AND BIOLOGICAL POTENTIAL." Journal of Applied Pharmaceutical Sciences and Research 6, no. 3 (December 14, 2023): 10–15. http://dx.doi.org/10.31069/japsr.v6i3.03.

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This review’s main focus is on the most recent synthesis of chalcones with N, O, or S heterocycles, highlighting their biological potential. Chalcone derivatives are considered in beneficial species because they possess a keto-ethylenic moiety, CO−CH=CH−. Due to the existence of a reactive α, β-unsaturated carbonyl group, the synthesis of chalcone derivatives, which have been physiologically explored for use against specific disease targets, has been made possible by recent advances in heterocyclic chemistry. The need for novel drugs that are effective against multidrug-resistant pathogens has been driven by the growth in antibiotic resistance brought on by a variety of reasons. Chalcones are phenolic compounds that fall within the flavonoids category. They are a part of a large category of naturally occurring bioactive substances. During this review we have gone through a number of studies where chalcones were created via Claisen Schmidt condensation of suitable acetophenone with suitable aromatic aldehydes in the presence of an aqueous solution of potassium hydroxide and ethanol at room temperature in an effort to create antibacterial agents. The review content have been obtained through web browsing on various scientific databases and search engines like Science Direct, Pub Med, Research Gate, Google Scholar, etc. The synthesis of diverse chalcone derivatives was motivated by the potential activity of naturally occurring chalcones as anticancer, anti-inflammatory, antibacterial, antioxidant, and antiparasitic characteristics, as well as by their unique chemical structural structure. Flavonoids and isoflavonoids, which are frequent chemical building blocks found in a variety of naturally derived compounds, are enhanced by chalcone. This review may prove to be helpful for the creation and design of new powerful therapeutic medications.

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Bala, Daniela, Luiza-Izabela Jinga, Marcela Popa, Anamaria Hanganu, Mariana Voicescu, Coralia Bleotu, Laszlo Tarko, and Simona Nica. "Design, Synthesis, and Biological Evaluation of New Azulene-Containing Chalcones." Materials 15, no. 5 (February 22, 2022): 1629. http://dx.doi.org/10.3390/ma15051629.

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Azulene-containing chalcones have been synthesized via Claisen–Schmidt condensation reaction. Their chemical structure has been established by spectroscopic methods where the 1H-NMR spectra suggested that the title chalcones were geometrically pure and configured trans (J = 15 Hz). The influence of functional groups from azulene-containing chalcones on the biological activity of the 2-propen-1-one unit was investigated for the first time. This study presents optical and fluorescent investigations, QSAR studies, and biological activity of 10 novel compounds. These chalcones were evaluated for their antimicrobial activity against Gram-positive and Gram-negative bacteria. The results revealed that most of the synthesized compounds showed inhibition against Gram-negative microorganisms, independent of the substitution of azulene scaffold. Instead, all azulene-containing chalcones exhibited good antifungal activity against Candida parapsilosis, with MIC values ranging between 0.156 and 0.312 mg/mL. The most active compound was chalcone containing azulene moieties on both sides of the 2-propene-1-one bond, exhibiting good activity against both bacteria-type strains and good antifungal activity. This antifungal activity combined with low toxicity makes azulene-containing chalcones a new class of bioorganic compounds.

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López, Génesis, Marco Mellado, Enrique Werner, Bastián Said, Patricio Godoy, Nelson Caro, Ximena Besoain, Iván Montenegro, and Alejandro Madrid. "Sonochemical Synthesis of 2’-Hydroxy-Chalcone Derivatives with Potential Anti-Oomycete Activity." Antibiotics 9, no. 9 (September 4, 2020): 576. http://dx.doi.org/10.3390/antibiotics9090576.

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This work reports on the synthesis of eight new 2′-hydroxy-chalcones with potential anti-phytopathogenic applications in agroindustry, AMONG others, via Claisen–Schmidt condensation and ultrasound assisted reaction. Assays showed three chalcones with allyl moieties strongly inhibited growth of phytopathogenic oomycete Phytophthora infestans; moreover, compound 8a had a half maximal effective concentration (EC50) value (32.5 µg/mL) similar to that of metalaxyl (28.6 µg/mL). A software-aided quantitative structure–activity relationship (QSAR) analysis of the whole series suggests that the structural features of these new chalcones—namely, the fluoride, hydroxyl, and amine groups over the carbon 3′ of the chalcone skeleton—increase anti-oomycete activity.

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Komoto, Tatiana, Tayná Bernardes, Thaís Mesquita, Luis Bortolotto, Gabriel Silva, Tamires Bitencourt, Seung Baek, Mozart Marins, and Ana Fachin. "Chalcones Repressed the AURKA and MDR Proteins Involved in Metastasis and Multiple Drug Resistance in Breast Cancer Cell Lines." Molecules 23, no. 8 (August 13, 2018): 2018. http://dx.doi.org/10.3390/molecules23082018.

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In the present investigation, trans-chalcone and licochalcone A were tested against MCF-7 and BT-20 breast cancer cell lines for anti-tumor activity. We found that both chalcones down regulated important genes associated to cancer development and inhibited cell migration of metastatic cells (BT-20). Finally, we observed that licochalcone A reduces the MDR-1 protein, while both chalcones suppress the AURKA protein in a dose-dependent manner. In conclusion, we observed the trans-chalcone and licochalcone A affected the cell viability of breast cancer cell lines MCF-7 and BT-20 and presents anti-metastatic and anti-resistance potential, by the repression of AUKA and MDR-1 proteins.

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Farooq, Saba, and Zainab Ngaini. "Recent Synthetic Methodologies for Chalcone Synthesis (2013-2018)." Current Organocatalysis 6, no. 3 (September 5, 2019): 184–92. http://dx.doi.org/10.2174/2213337206666190306155140.

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An up-to-date short review of the chalcone methodologies is presented, which is the most interesting and beneficial for choosing the desired protocol to synthesize suitable derivatives of chalcones. Chalcones are fluorescent, stable compounds which contribute to the synthesis of various pharmacologically important heterocyclic structure-based derivatives. Chalcone has displayed a remarkable curative efficiency to cure several diseases. Several schemes and methodologies have been reported for employing different catalysts and reagents. The development of improved methodologies of α, β-unsaturated carbonyl compounds is still on going. In this review, synthetic methodologies and their recent modification in designing new methods with efficient, economical, eco-friendly and high yield are discussed.

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Coskun, Demet, Misir Ahmedzade, and Sevda Kirbag. "3-(Substituted Aryl)-1-benzofuranyl-2-propenones: Antimicrobial Properties of Some Chalcones-Type Compounds and their 2-Pyrazoline Derivatives." E-Journal of Chemistry 8, no. 4 (2011): 1574–81. http://dx.doi.org/10.1155/2011/806854.

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2-Acetylbenzofuran on condensation with furan-2-carboxaldehyde and pyrrole-2-carboxaldehyde in methanolic KOH solution yielded the corresponding benzofuran chalcones. These two compounds and nine benzofuran chalcones were synthesized before, were further reacted with hydrazine hydrate in ethanol which led to the formation of 2-pyrazoline derivatives. All the synthesized compounds were characterized by elemental analysis, melting point determination, infrared spectroscopy and nuclear magnetic resonance spectroscopy. Nine chalcone-type compounds and eleven 2-pyrazolines were evaluated for their biological activities against the six bacteria and the three yeast and it was seen that thirteen compounds showed activity. Four of them are chalcone-type compounds showed more or less activity.

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Hba, Soufyane, Suzan Ghaddar, Hicham Wahnou, Aline Pinon, Riad El Kebbaj, Christelle Pouget, Vincent Sol, Bertrand Liagre, Mounia Oudghiri, and Youness Limami. "Natural Chalcones and Derivatives in Colon Cancer: Pre-Clinical Challenges and the Promise of Chalcone-Based Nanoparticles." Pharmaceutics 15, no. 12 (December 1, 2023): 2718. http://dx.doi.org/10.3390/pharmaceutics15122718.

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Colon cancer poses a complex and substantial global health challenge, necessitating innovative therapeutic approaches. Chalcones, a versatile class of compounds with diverse pharmacological properties, have emerged as promising candidates for addressing colon cancer. Their ability to modulate pivotal signaling pathways in the development and progression of colon cancer makes them invaluable as targeted therapeutics. Nevertheless, it is crucial to recognize that although chalcones exhibit promise, further pre-clinical studies are required to validate their efficacy and safety. The journey toward effective colon cancer treatment is multifaceted, involving considerations such as optimizing the sequencing of therapeutic agents, comprehending the resistance mechanisms, and exploring combination therapies incorporating chalcones. Furthermore, the integration of nanoparticle-based drug delivery systems presents a novel avenue for enhancing the effectiveness of chalcones in colon cancer treatment. This review delves into the mechanisms of action of natural chalcones and some derivatives. It highlights the challenges associated with their use in pre-clinical studies, while also underscoring the advantages of employing chalcone-based nanoparticles for the treatment of colon cancer.

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Mahapatra, Debarshi K., Soumajit Ghorai, Sanjay K. Bharti, Asmita G. Patil, and Shovanlal Gayen. "Current Discovery Progress of Some Emerging Anti-infective Chalcones: Highlights from 2016 to 2017." Current Drug Discovery Technologies 17, no. 1 (April 17, 2020): 30–44. http://dx.doi.org/10.2174/1570163815666180720170030.

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The anti-infective potentials of the natural products are very well known for centuries and are a part of traditional healing. The foremost therapeutic classes include flavones, isoflavones, flavonols, flavanones, flavanols, proanthocyanidins, anthocyanidins, chalcones, and aurones. The chalcone or 1,3-diphenyl-2E-propene-1-one represents the class of natural products which are comprised of benzylideneacetophenone function; i.e. two aromatic moieties linked together by an α, β-unsaturated carbonyl bridge comprising three-carbons. At present, chalcone is one of the privileged scaffolds that can be synthesized in the laboratory to derive different pharmacologically active compounds. This article is the continued form of the previously published work on anti-infective perspectives of chalcones (highlighted till 2015). The current work emphasizes on the discovery process of the chalcone in the period of 2016 to 2017 on malaria, trypanosomiasis, leishmaniasis, filaria, tuberculosis, netamodes, Human Immunodeficiency Virus (HIV), Tobacco Mosaic Virus (TMV), Severe Acute Respiratory Syndrome (SARS), and miscellaneous conditions. This review comprehensively focuses on the latest progress related with the anti-infective chalcones. The content includes the crucial structural features of chalcone scaffold including structure-activity relationship(s) along with their plausible mechanism of action(s) from the duration Jan 2016 to Dec 2017. This literature will be of prime interest to medicinal chemists in getting ideas and concepts for better rational development of potential anti-infective inhibitors.

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Federič, Jozef, and Štefan Toma. "Michael additions to metallocene analogues of chalcones." Collection of Czechoslovak Chemical Communications 52, no. 1 (1987): 174–81. http://dx.doi.org/10.1135/cccc19870174.

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Eleven analogues of chalcones were synthesized; the variously substituted ferrocenyl, ruthenocenyl or η5-cyclopentadienyltricarbonylmanganese are attached to the β-carbon of the chalcone double bond. Methyl malonate was added to eight selected chalcones. The effect of an aryl group on the chemical shift difference of diastereotopic -COOCH3 groups is discussed. The Vilsmeier-Haack formylation was employed to prepare 1'-chloro and 1'-bromoferrocenecarbaldehydes. The synthesis of 2-chloroferrocenecarbaldehyde from 2-chloroferrocenylmethyldimethylamine is also described.

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Ivanova, A. B., D. I. Batovska, I. T. Todorova, B. A. Stamboliyska, J. Serly, and J. Molnar. "Comparative Study on the MDR Reversal Effects of Selected Chalcones." International Journal of Medicinal Chemistry 2011 (February 6, 2011): 1–7. http://dx.doi.org/10.1155/2011/530780.

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Based on the structure of three previously established lead compounds, fifteen selected chalcones were synthesized and evaluated for their multidrug resistance (MDR) reversal activity on mouse lymphoma cells. The most active chalcones were stronger revertants than the positive control, verapamil. In the model of combination chemotherapy, the interactions between the anticancer drug doxorubicin and two of the most effective compounds were measured in vitro, on human MDR1 gene transfected mouse lymphoma cells, showing that the type of interaction for one of these compounds was indifferent while that for the other one was additive. Furthermore, two chalcones inhibited 50% of cell proliferation in concentration of around 0.4 μg/mL and were from 2- to 100-fold more active than the most chalcones. The structure-activity relationships were obtained and discussed in view of their usefulness for the design of chalcone-like P-gp modulators and drugs able to treat resistant cancers.

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Wijayanti, Lucia Wiwid, Respati Tri Swasono, Wonkoo Lee, and Jumina Jumina. "Synthesis and Evaluation of Chalcone Derivatives as Novel Sunscreen Agent." Molecules 26, no. 9 (May 4, 2021): 2698. http://dx.doi.org/10.3390/molecules26092698.

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Ultraviolet (UV) irradiation is a serious problem for skin health thus the interest in the research to develop sunscreen agent has been increasing. Chalcone is a promising compound to be developed as its chromophore absorbs in the UV region. Therefore, in the present work, we synthesized eight chalcone derivatives through Claisen–Schmidt condensation at room temperature. The evaluation of the optical properties of each chalcone derivatives in the UV region was conducted through spectroscopic and computational studies. The synthesized chalcones were obtained in good yields and they were active in the UV region. The results revealed that more methoxy substituents to chalcone leads toward red shift. All chalcone derivatives have high molar absorptivity value (21,000–56,000) demonstrating that they have the potential to be used as the sunscreen agent. The cytotoxicity assay showed that chalcone derivatives were demonstrating low toxicity toward normal human fibroblast cell, which is remarkable. Therefore, we concluded that the synthesized chalcones in this work were potential to be developed as novel sunscreen agents in real application.

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Osman, Marwa S., Talal A. Awad, Shaza W. Shantier, Elrashied A. E. Garelnabi, Moawia M. Mukhtar, Wadah Osman, Ramzi A. Mothana, and Rashid I. Elhag. "Insights into the molecular basis of some chalcone analogues as potential inhibitors of Leishmania donovani: An integrated in silico and in vitro study." Open Chemistry 20, no. 1 (January 1, 2022): 680–93. http://dx.doi.org/10.1515/chem-2022-0160.

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Abstract Protozoal infections caused by species belonging to Leishmania donovani complex are responsible for the most severe form of leishmaniasis, especially in Sudan and other developing countries. Drugs commonly used for the treatment of the disease show varying levels of effectiveness and also have associated side effects. Thus, the present work highlights the synthesis of some chalcones to be used as potential anti-leishmanial agents. The activity of the synthesized chalcones has been evaluated against L. donovani. The ADMET profile of the synthesized compounds were tested using various integrated web-based tools. Moreover, in order to investigate the molecular mechanism of action, the chalcone compounds were docked into L. donovani trypanothione reductase (TR) using Autodock 4.0 and molecular dynamics were studies. Eight compounds showed the highest activity against the morphological forms. Among these compounds, chalcones 15 has shown the highest inhibitory effect with IC50 value of 1.1 µM. In addition, pharmacokinetic and toxicological investigations revealed its good oral bioavailability and low toxicity. Furthermore, chalcone 15 was found to interact with high affinity (−13.7 kcal/mol) with TR, an essential enzyme for the leishmanial parasite. Thus, this promising activity against L. donovani supports the use of chalcone 15 as a potential new therapy for visceral leishmaniasis.

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Letulle, Cécile, François-Xavier Toublet, Aline Pinon, Soufyane Hba, Aurélie Laurent, Vincent Sol, Catherine Fagnère, et al. "Synthesis and Antiproliferative Effect of 3,4,5-Trimethoxylated Chalcones on Colorectal and Prostatic Cancer Cells." Pharmaceuticals 17, no. 9 (September 13, 2024): 1207. http://dx.doi.org/10.3390/ph17091207.

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In the context of designing innovative anticancer agents, the synthesis of a series of chalcones bearing a 3,4,5-trimethoxylated A ring and a variety of B rings, including phenols and original heterocycles such as chromones, was conducted. For this end, Claisen–Schmidt condensation was performed in basic or acidic conditions between the common starting material 3,4,5-trimethoxyacetophenone and appropriate aldehydes; this allowed the recovery of fifteen chalcones in moderate–good yields. The synthesized compounds were screened for their antiproliferative activity against colorectal and prostatic cancer cells, using a colorimetric MTT assay. Among the new chromonyl series, chalcone 13 demonstrates an interesting antiproliferative effect, with IC50 values in the range of 2.6–5.1 µM at 48 h. Then, our study evidenced that indolyl chalcone 10 exhibits excellent activity towards the selected cell lines (with IC50 less than 50 nM). This compound has already been described and has been shown to be a potent anticancer agent against other cancer cell lines. Our investigations highlighted apoptosis induction, through several pro-apoptotic markers, of these two heterocyclic chalcones. Considering phenolic chalcones, compounds 2 and 8 were found to be the most active against cell proliferation, exerting their effect by inducing the depolymerization of cell microtubules. The most promising compounds in this series will be selected for application in a strategy of vectorization by either active or passive targeting.

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Novilla, Arina, Mustofa Mustofa, Indwiani Astuti, Jumina Jumina, and Hery Suwito. "Cytotoxic Activity of Methoxy-4’amino Chalcone Derivatives Against Leukemia Cell Lines." Molecular and Cellular Biomedical Sciences 3, no. 1 (March 1, 2019): 34. http://dx.doi.org/10.21705/mcbs.v3i1.44.

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Background: Chemotherapy is a common treatment for leukemia as well as in other cancer treatment. The lack of tumor selectivity and development of multi-drug resistance by chemotherapy caused the development of new strategy in cancer treatment become a pressing need. This study was performed to evaluate the anticancer activity and selectivity of seven derivatives of chalcones against K562 and HL-60 leukemia cell lines. Materials and Methods: The cytotoxicity of chalcone’s seven derivatives (compound 1-7) was tested by using MTS (3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxyme-thoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium) method. The percentage of cell mortality data was calculated then the IC50 was analyzed using probit analysis (SPSS 17). The selectivity index (SI) then calculated from IC50 ratio of normal lymphocyte cells and cancerous cells line (HL-60 and K562).Results: The IC50 of almost all seven tested compounds were lower in HL-60 cell lines than K562 cell lines, except for Compound 7. The number and position of methoxy groups in chalcone derivatives influenced the anticancer and cancer selectivity of chalcone derivatives.Conclusion: The results revealed that the number and position of methoxy groups in chalcone derivatives influenced the anticancer and cancer selectivity of chalcone derivatives.Keywords: anticancer, chalcone derivatives, methoxy-4’-amino chalcone, leukemia, cytotoxic, selectivity

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Salotra, Riddhi, and Divya Utreja. "A Comprehensive Appraisal of Chalcones and Their Heterocyclic Analogs as Antimicrobial Agents." Current Organic Chemistry 24, no. 23 (December 28, 2020): 2755–81. http://dx.doi.org/10.2174/1385272824999200922090524.

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Owing to the growing demand for compelling antimicrobial agents, chalcones and their heterocyclic derivatives have engrossed prodigious attention of medicinal chemists as an effective clinical template for the synthesis of such agents on account of their structural diversity and molecular flexibility. Chalcones are considered as a fortunate scaffold in the field of both synthetic as well as natural product chemistry. They are reflected as a remarkable section of logically occurring pharmacophores that possess a comprehensive scale of biological activities, such as anti-cancer, anti-malarial, anti-viral and anti-inflammatory, rendering them with a high degree of assortment and noble therapeutic profile. They act as a crucial intermediate for the synthesis of novel heterocyclic skeletons holding biodynamic behavior. This review emphasizes on different aspects of chalcones including their natural sources, recent synthetic methodologies and evaluation of their anti-microbial potential. It is expected as a persuasive compilation on chalcones that may benefit the experts to design potent and less toxic chalcone referents as medicinal agents.

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B, Ravindar, Srinivasa Murthy M, and Afzal Basha Shaik. "DESIGN, FACILE SYNTHESIS, AND BIOLOGICAL EVALUATION OF NOVEL 1,3-THIAZINE DERIVATIVES AS POTENTIAL ANTICONVULSANT AGENTS." Asian Journal of Pharmaceutical and Clinical Research 9, no. 5 (September 1, 2016): 272. http://dx.doi.org/10.22159/ajpcr.2016.v9i5.13676.

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ABSTRACTObjective: Chalcones and their heterocyclic analogs represent an important class of small molecules having anticonvulsant activities. Therefore, inthis study, the synthesis and anticonvulsant activity of some new chalcones and 1,3-thiazines were described.Methods: The reaction of 1-acetylnaphthalene with substituted aromatic aldehydes in the presence of aq. NaOH afforded corresponding chalconeswhich upon further cyclization with thiourea resulted in 1,3-thiazine derivatives. The newly synthesized compounds were tested for anticonvulsantactivity by pentylenetetrazole-induced seizures method using diazepam as standard.Results: Most of the compounds showed good anticonvulsant activity but is less than diazepam. 1,3-thiazines were more potent than chalconesand among them, compound P4 containing 4-fluorophenyl substituents on the thiazine moiety was more potent as it has prolonged the onset ofconvulsions by 155.2 seconds.Conclusion: We described the synthesis and anticonvulsant activity of novel chalcones and 1,3-thiazine derivatives. 1,3-thiazines are more activeanticonvulsant agents than chalcones and in particular compounds with electron withdrawing substituents.Keywords: Chalcone, 1,3-thiazine, Pentylenetetrazole.

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Ali, R., A. Rahim, and A. Islam. "Synthesis and Antimicrobial Activity of 7-Hydroxy-3',4'-Methylenedioxy- and 7-Benzyloxy-3',4'-Methylenedioxy Flavanones." Journal of Scientific Research 9, no. 3 (September 1, 2017): 297–306. http://dx.doi.org/10.3329/jsr.v9i3.31229.

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7-Hydroxy-3',4'-methylenedioxy- and 7-benzyloxy-3',4'-methylenedioxy flavanones have been synthesized starting from 2,4-dihydroxyacetophenone. Subsequently biocidal activities of the flavanones have been investigated along with their corresponding chalcones against some bacterial and fungal strains. 2'-Hydroxy-4'-benzyloxy-3,4-methylenedioxy chalcone (5) and its corresponding flavanone (7) showed good antibacterial and antifungal activities against some selected bacterial and fungal strains. On the other hand, 2',4'-dihydroxy-3,4-methylenedioxy chalcone (4) showed no antibacterial and antifungal activities while its corresponding flavanone (6) showed a little antibacterial activity only at higher concentration but did not show antifungal activity. The synthesized chalcones and flavanones have been characterized using UV-Vis, IR and 1H NMRspectral data together with elemental analysis.

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Das, Manik, and Kuntal Manna. "Chalcone Scaffold in Anticancer Armamentarium: A Molecular Insight." Journal of Toxicology 2016 (2016): 1–14. http://dx.doi.org/10.1155/2016/7651047.

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Cancer is an inevitable matter of concern in the medicinal chemistry era. Chalcone is the well exploited scaffold in the anticancer domain. The molecular mechanism of chalcone at cellular level was explored in past decades. This mini review provides the most recent updates on anticancer potential of chalcones.

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Olbrykh, Arina, Aleksei Titov, Alexander Smol’yakov, Oleg Filippov, and Elena S. Shubina. "Exploring the Interaction of Pyridine-Based Chalcones with Trinuclear Silver(I) Pyrazolate Complex." Inorganics 11, no. 4 (April 21, 2023): 175. http://dx.doi.org/10.3390/inorganics11040175.

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The investigation of the interaction of cyclic trinuclear silver(I) pyrazolate [AgPz]3 (Pz = 3,5-bis(trifluoromethyl)pyrazolate) with pyridine-based chalcones (anthracen-9-yl and phenyl-substituted ones) has been performed by IR-, UV-vis, and NMR spectroscopies in the solution. The carbonyl group participates in coordination with metal ions in all complexes. However, the network of π-π/M-π non-covalent intermolecular interactions mainly influences complex formation. The spectral data suggest retaining the structures for all studied complexes in the solution and solid state. E-Z isomerization in the case of anthracene-containing compounds significantly influences the complexation. E-isomer of chalcones seeks the planar structure in the complexes with [AgPz]3. In contrast, the Z-isomer of chalcone demonstrates the chelating coordination of O- and N atoms to silver ions. The complexation of anthracene-containing chalcones allows the switching of the emission nature from charge transfer to ligand-centered at 77 K. In contrast, phenyl-substituted chalcone in complex with macrocycle demonstrates that the emission significantly shifted (Δ = ca. 155 nm) to the low-energy region compared to the free base.

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Montes-González, Ingrid, Ambar M. Alsina-Sánchez, Juan C. Aponte-Santini, Sara M. Delgado-Rivera, and Geraldo L. Durán-Camacho. "Perspectives of ferrocenyl chalcones: synthetic scaffolds toward biomedical and materials science applications." Pure and Applied Chemistry 91, no. 4 (April 24, 2019): 653–69. http://dx.doi.org/10.1515/pac-2018-0802.

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Abstract Ferrocene and its derivatives constitute versatile and interesting scaffolds for the global chemical enterprise due to its multiple applications that range from biomedical to materials science. Ferrocenyl derivatives are the leading compounds in our research for the syntheses and characterization as well as their potential biological applications. Among them, our recent focus has been in ferrocenyl chalcones as a framework for further derivatization. The proposed modifications consist on the incorporation of heterocyclic moieties into the ferrocenyl chalcone core. This can be afforded either by introducing a heterocyclic aromatic moiety as a substituent or functionalizing the α-β unsaturated system. Another modification explored is the formation of ammonium or pyridinium salts to increase water solubility. Studied ferrocenyl chalcones exhibit remarkable stability, physical, and electrochemical properties. These factors have led the approaches for them to be precursors of biologically active compounds (cancer, bacteria, malaria, and neurobiological diseases). Moreover, other potential applications include molecular materials, redox-sensors, and polymers. Our goal in this mini review is to highlight the chemistry of ferrocene derivatives with particular prominence to those ferrocenyl chalcones studied in our laboratory and their applications. Moreover, we are providing a background on ferrocene, chalcones, and ferrocenyl chalcones, emphasizing the methodologies with preeminent yields.

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Mathew, Bijo, Della Grace Thomas Parambi, Vishnu Sankar Sivasankarapillai, Md Sahab Uddin, Jerad Suresh, Githa Elizabeth Mathew, Monu Joy, Akash Marathakam, and Sheeba Varghese Gupta. "Perspective Design of Chalcones for the Management of CNS Disorders: A Mini-Review." CNS & Neurological Disorders - Drug Targets 18, no. 6 (August 30, 2019): 432–45. http://dx.doi.org/10.2174/1871527318666190610111246.

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: The development of chalcone-based compounds for CNS disorders has been explored by many research groups. Chalcones are being considered as a potent organic scaffold with widespread applications in the field of drug discovery and medicinal chemistry. The planar or semi-planar geometry of chalcones with various functionalities impinged on the terminal aromatic systems renders the molecule its bio-activity including anti-cancer, anti-malarial, anti-microbial, anti-fungal, antileishmanial, anti-viral, anti-diabetic, anti-hypertensive properties, etc. Moreover, cutting-edge research has been executed in the domain of Central Nervous System (CNS) based scheme, further, their identification and classifications also remain of high interest in the field of medicinal chemistry but the specific reviews are limited. Hence, the present review highlights the significance of chalcones toward their CNS activities (up to 2019), which include anti-depressant activity, anxiolytic activity, activity with GABA receptors, acetylcholinesterase (AChE) and butyryl cholinesterase (BChE) inhibitions, activity as adenosine receptor antagonists anti-Alzheimer’s agents, β-amyloid plaques imaging agents, monoamine oxidase inhibition. To our knowledge, this is the first review exclusively for CNS activity profile of chalcones.

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Journal, Baghdad Science. "Synthesis and Characterization of Some Novel Oxazine, Thiazine and Pyrazol Derivatives." Baghdad Science Journal 13, no. 2 (June 5, 2016): 244–52. http://dx.doi.org/10.21123/bsj.13.2.244-252.

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In this paper, some chalcone derivatives (C1, C2) were synthesized based on the reaction of equal amount of substituted acetophenone and substituted banzaldehyde in basic medium. Oxazine and thiazine derivatives were prepared from the reaction of chalcones (C1-C2) with urea and thiourea respectively in a basic medium. Pyrazole derivatives were prepared based on the reaction of chalcones with hydrazine mono hydrate or phenyl hydrazine in the presence of glacial acetic acid as a catalyst. The new synthesized compounds were identified using various physical techniques like1 H-NMR and FT-IR spectra.

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Coşkun, Demet, Suat Tekin, Süleyman Sandal, and Mehmet Fatih Coşkun. "Synthesis, Characterization, and Anticancer Activity of New Benzofuran Substituted Chalcones." Journal of Chemistry 2016 (2016): 1–8. http://dx.doi.org/10.1155/2016/7678486.

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Benzofuran derivatives are of great interest in medicinal chemistry and have drawn considerable attention due to their diverse pharmacological profiles including anticancer activity. Similarly, chalcones, which are common substructures of numerous natural products belonging to the flavonoid class, feature strong anticancer properties. A novel series of chalcones, 3-aryl-1-(5-bromo-1-benzofuran-2-yl)-2-propanones propenones (3a–f), were designed, synthesized, and characterized.In vitroantitumor activities of the newly synthesized (3a–f) and previously synthesized (3g–j) chalcone compounds were determined by using human breast (MCF-7) and prostate (PC-3) cancer cell lines. Antitumor properties of all compounds were determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Cell viability assay for the tested chalcone compounds was performed and thelog⁡IC50values of the compounds were calculated after 24-hour treatment. Our results indicate that the tested chalcone compounds show antitumor activity against MCF-7 and PC-3 cell lines (p<0.05).

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Pragi, Jagdeep Singh Dua, and Jitender Singh. "Chalcone Ditosylates as Potent Precursor for Synthesis of Some 4,5-Disubstituted Isoxazoles with Antioxidant and Anti-inflammatory Activities." Asian Journal of Chemistry 31, no. 8 (June 28, 2019): 1847–50. http://dx.doi.org/10.14233/ajchem.2019.22077.

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The present work emphasizes on the synthesis of a series of 4,5-disubstituted isoxazole derivatives of α,β-chalcone ditosylates which were synthesized by the reaction of α,β-chalcone ditosylates with hydroxylamine hydrochloride. Various α,β-chalcone ditosylates were prepared by the reaction of respective chalcones with hydroxyl (tosyloxy)iodobenzene.The synthesized compounds were characterized and subsequently evaluated for anti-inflammatory and antioxidant properties.

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Sahu, Adarsh, Shweta Mishra, Asmita Gajbhiye, and Ram Kishore Agrawal. "Magnesium Perchlorate Catalyzed Phospha-Michael Addition of Dialkyl Phosphite to Chalcone." Current Organic Synthesis 15, no. 7 (October 16, 2018): 1020–23. http://dx.doi.org/10.2174/2210315508666180103162452.

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Aim and Objective: Phosphonate possesses a broad range of applications ranging from agrochemistry to medicines. Because of the synthetic and biological importance of phosphonate, their chemistry has stimulated an increasing interest. Hence we developed an efficient and eco-friendly Mg(ClO4)2 catalyzed one pot, solvent free synthesis of phosphonate derivatives of chalcones. Materials and Methods: Magnesium perchlorate phosphonate derivatives of chalcones were synthesized. The reactions were executed at room temperature in the presence of Anhydrous Magnesium perchlorate Anhy. Mg(ClO4)2 under solvent free condition, affording high yield of the product. The cardinal significance of the method lies in its uncomplicated and eco- friendly experimental conditions. Results: The PMA method for P-C bond formation, using dialkyl phosphite with chalcone, was performed in the presence of Anhydrous Magnesium perchlorate under solvent free condition. Despite the solvent free condition, the methodology is efficient since it is required only in catalytic amount of Anhy. Mg(ClO4)2 in one pot reaction. Results demonstrated that the catalytic PMA of dimethyl phosphite, diethyl phosphite, diisopropyl phosphite and dibutyl phosphite with chalcone generates desired products with a percentage yield of 60-80%. Conclusion: We have developed a new efficient PMA method for P-C bond formation, using dialkyl phosphite with α,β-unsaturated ketone i.e. chalcone. To the best of our knowledge, Anhy. Mg(ClO4)2 catalyzed phosphamicheal addition of dialkyl phosphite with chalcones was found to be a new and efficient method for various biological applications.

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Popova, Milena, Vassya Bankova, Stefan Spassov, Iva Tsvetkova, Mario Vides Silva, Maria Tsartsarova, and Christo Naydenski. "New Bioactive Chalcones in Propolis from El Salvador." Zeitschrift für Naturforschung C 56, no. 7-8 (August 1, 2001): 593–96. http://dx.doi.org/10.1515/znc-2001-7-819.

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2′,3′-Dihydroxy-4,4′-dimethoxychalcone (1) and 2′,3′,4-trihydroxy-4′-methoxy-chalcone, two new chalcones, were isolated from propolis from El Salvador. The compounds showed significant antibacterial ana antifunfag activity and moderate toxicity to Artemia salina nauplii

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Fatima, Miraj, Samina Aslam, Ansa Madeeha Zafar, Ali Irfan, Misbahul Ain Khan, Muhammad Ashraf, Shah Faisal, et al. "Exploring the Synthetic Chemistry of Phenyl-3-(5-aryl-2-furyl)- 2-propen-1-ones as Urease Inhibitors: Mechanistic Approach through Urease Inhibition, Molecular Docking and Structure–Activity Relationship." Biomedicines 11, no. 9 (August 30, 2023): 2428. http://dx.doi.org/10.3390/biomedicines11092428.

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Furan chalcone scaffolds belong to the most privileged and promising oxygen-containing heterocyclic class of compounds, which have a wide spectrum of therapeutic applications in the field of pharmaceutics, pharmacology, and medicinal chemistry. This research described the synthesis of a series of twelve novel and seven reported furan chalcone (conventional synthetic approach) analogues 4a–s through the application of microwave-assisted synthetic methodology and evaluated for therapeutic inhibition potential against bacterial urease enzyme. In the first step, a series of nineteen substituted 5-aryl-2-furan-2-carbaldehyde derivatives 3a–s were achieved in moderate to good yields (40–70%). These substituted 5-aryl-2-furan-2-carbaldehyde derivatives 3a–s were condensed with acetophenone via Claisen–Schmidt condensation to furnish 19 substituted furan chalcone scaffolds 4a–s in excellent yields (85–92%) in microwave-assisted synthetic approach, while in conventional methodology, these furan chalcone 4a–s were furnished in good yield (65–90%). Furan chalcone structural motifs 4a–s were characterized through elemental analysis and spectroscopic techniques. These nineteen (19)-afforded furan chalcones 4a–s were screened for urease inhibitory chemotherapeutic efficacy and most of the furan chalcones displayed promising urease inhibition activity. The most active urease inhibitors were 1-phenyl-3-[5-(2′,5′-dichlorophenyl)-2-furyl]-2–propen-1-one 4h with an IC50 value of 16.13 ± 2.45 μM, and 1-phenyl- 3-[5-(2′-chlorophenyl)-2-furyl] -2-propen-1-one 4s with an IC50 value of 18.75 ± 0.85 μM in comparison with reference drug thiourea (IC50 = 21.25 ± 0.15 μM). These furan chalcone derivatives 4h and 4s are more efficient urease inhibitors than reference drug thiourea. Structure–activity relationship (SAR) revealed that the 2,5-dichloro 4h and 2-chloro 4s moiety containing furan chalcone derivatives may be considered as potential lead reagents for urease inhibition. The in silico molecular docking study results are in agreement with the experimental biological findings. The results of this study may be helpful in the future drug discovery and designing of novel efficient urease inhibitory agents from this biologically active class of furan chalcones.

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Journal articles on the topic 'Chalcones'

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