Journal articles: 'Hydrazones'

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Ji, Heng, Hui-qiong Ni, Peng Zhi, et al. "Visible-light mediated directed perfluoroalkylation of hydrazones." Organic & Biomolecular Chemistry 15, no. 28 (2017): 6014–23. http://dx.doi.org/10.1039/c7ob01144j.

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A convenient and efficient protocol was reported to access a series of perfluoroalkylated aromatic aldehyde hydrazones. Aliphatic aldehyde hydrazones and N-monosubstituted hydrazones which are unreactive in previously reported hydrazone perfluoroalkylation reactions now take part in the reaction.

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KushalNath Mishra, Shambaditya Goswami, Kumudhavalli M.V, et al. "Hydrazones and their metal complexes: A short review on their biological potentia." International Journal of Research in Pharmaceutical Sciences 11, SPL4 (2020): 1440–47. http://dx.doi.org/10.26452/ijrps.v11ispl4.4319.

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Hydrazones belong to complexes are beneficial in different fields for their essential role in the development of a range of stable complexes in the coordination chemistry. Different researchers have reported the various medicinal properties of hydrazones. Hydrazone and its metal complexes are useful for the detection of some organic components from pharmaceutical formulations. These metallic compounds act as a catalyst for conducting various chemical reactions and help in making different chemical complexes that are effective against bacteria, fungi, and many other microbes. Aromatic hydrazone derivatives can measure the concentration of low molecular weight aldehyde and ketone complexes. Hydrazones possess numerous medicinal properties, including antimicrobial, anti-cancer, antidepressant, anti-tubercular, anti-viral, etc. For the new drug discovery, hydrazones/azomethines are considered to be an important class of compound. From molecular biology to pharmaceutical formulation, organic chemistry, new drug development process, the importance of hydrazone and its metal complexes is immense. The present review aims to highlight the reported biological activities related to hydrazones for the last decade.

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Asif, Mohammad, and Asif Husain. "Analgesic, Anti-Inflammatory, and Antiplatelet Profile of Hydrazones Containing Synthetic Molecules." Journal of Applied Chemistry 2013 (December 17, 2013): 1–7. http://dx.doi.org/10.1155/2013/247203.

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Hydrazones are present in many of the bioactive compounds with wide interest because of their diverse pharmacological applications. Hydrazones possess wide variety of biological activities such as anticonvulsant, antidepressant, analgesic, anti-inflammatory, antiplatelet, antimicrobial, anticancer, antihypertensive, anthelmintic, antidiabetic, antiparasitic, and other anticipated activities. This created an interest for researchers towards synthesized variety of hydrazone derivatives for different biological activities. Therefore many researchers have synthesized hydrazone derivatives as target structures for their biological activities. This is paper focuses on the analgesic, anti-inflammatory, and antiplatelet activities of hydrazones.

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Kajal, Anu, Suman Bala, Neha Sharma, Sunil Kamboj, and Vipin Saini. "Therapeutic Potential of Hydrazones as Anti-Inflammatory Agents." International Journal of Medicinal Chemistry 2014 (March 4, 2014): 1–11. http://dx.doi.org/10.1155/2014/761030.

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Hydrazones are a special class of organic compounds in the Schiff base family. Hydrazones constitute a versatile compound of organic class having basic structure (R1R2C=NNR3R4). The active centers of hydrazone, that is, carbon and nitrogen, are mainly responsible for the physical and chemical properties of the hydrazones and, due to the reactivity toward electrophiles and nucleophiles, hydrazones are used for the synthesis of organic compound such as heterocyclic compounds with a variety of biological activities. Hydrazones and their derivatives are known to exhibit a wide range of interesting biological activities like antioxidant, anti-inflammatory, anticonvulsant, analgesic, antimicrobial, anticancer, antiprotozoal, antioxidant, antiparasitic, antiplatelet, cardioprotective, anthelmintic, antidiabetic, antitubercular, trypanocidal, anti-HIV, and so forth. The present review summarizes the efficiency of hydrazones as potent anti-inflammatory agents.

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Šandrik, Róbert, Pavol Tisovský, Klaudia Csicsai, et al. "ON/OFF Photostimulation of Isatin Bipyridyl Hydrazones: Photochemical and Spectral Study." Molecules 24, no. 14 (2019): 2668. http://dx.doi.org/10.3390/molecules24142668.

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Four novel isatin hydrazones containing bipyridyl fragments were synthesized as potential ON/OFF switches. Hydrazone Z-isomers exhibit high thermal stability. The characteristic photochemical reaction for all studied hydrazones is the Z–E isomerization in CHCl3. After irradiation of hydrazones 1 and 2 in dimethylformamide (DMF), the photoreaction products are tautomers. When using light with the appropriate wavelength, the photo-tautomerization reaction is reversible. In these conditions, studied hydrazones have ON/OFF switch properties. In the case of hydrazones 1 and 2, by alternating heat and light stimulation it is possible to control the isomerization process reversibly. In the presence of fluoride ions, NH hydrogen from the studied hydrazones is cleaved, and the corresponding anions are formed. The resulting anions of Z-isomers are changed to the corresponding E-isomer at room temperature.

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Jollimore, Jason V., Marc Vacheresse, Keith Vaughan, and Donald L. Hooper. "The effect of ortho and para substituents on the formation of the E and Z isomers of the arylhydrazones obtained from diazonium coupling with methyl 3-aminocrotonate and 3-aminocrotononitrile." Canadian Journal of Chemistry 74, no. 2 (1996): 254–62. http://dx.doi.org/10.1139/v96-029.

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Reaction of arene diazonium salts with 3-aminocrotononitrile or methyl 3-aminocrotonate affords the 2-aryl-hydrazono-3-oxobutanenitrile (1 or 3 and 3′) or the methyl 2-arylhydrazono-3-oxobutanoate (2 and 2′ or 4 and 4′). A series of these hydrazones has been prepared with a range of electron-withdrawing and -donating substituents in the ortho or para position of the aryl moiety. The hydrazones have been characterized by spectroscopic methods, with emphasis on the 1H NMR spectra, which have been used to determine the configuration of the hydrazones as E or Z or a mixture of the two. The para-substituted hydrazononitriles (1) are formed as a single species, namely the Z isomer, whereas the ortho isomers are formed as a mixture of E and Z configurations (3 and 3′). The hydrazonobutanoates (2 and 2′ or 4 and 4′) are formed as E/Z mixtures regardless of the position of the substituent in the aryl moiety. Complete assignments of all signals in the 1H NMR spectra have been made on the basis of the ability of the various substituents to participate in intramolecular hydrogen bonding and a mechanism is proposed to account for the variations in the proportions of E and Z isomers and the effect of the nature of the substituent on this ratio. 13C NMR spectra of selected hydrazones have been recorded as an aid to structure assignment. Key words: hydrazone, diazonium, NMR spectroscopy, E/Z isomers, crotonic acid derivatives.

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Sihag, Monika, and Rinku Soni. "HTIB as an Efficient and Convenient Reagent for Oxidative Cleavage of C=N in Pyrimidinyl Hydrazones." Indian Journal of Heterocyclic Chemistry 33, no. 04 (2023): 393. http://dx.doi.org/10.59467/ijhc.2023.33.393.

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This study is aimed to explore the efficiency of [hydroxy(tosyloxy)iodo]benzene (HTIB) in the oxidative cleavage of some pyrimidinyl hydrazones. The protocol involves stirring the hydrazone derivatives with HTIB in dichloromethane at room temperature. The oxidative cleavage of C = N in pyrimidinyl hydrazones regenerated parent ketones in high yields. The methodology has advantage of preventing over oxidation of carbonyl functionality.

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Wahbeh, Jenna, and Sarah Milkowski. "The Use of Hydrazones for Biomedical Applications." SLAS TECHNOLOGY: Translating Life Sciences Innovation 24, no. 2 (2019): 161–68. http://dx.doi.org/10.1177/2472630318822713.

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The use of hydrazones presents an opportunity for enhancing drug delivery through site-specific drug release, including areas such as tumor tissue or thrombosis. Many researchers are experimenting on how to more efficiently form these hydrazones, specifically using heat and chemical catalysts. Hydrazones respond on the pH environment or are synthesized with particular functional groups of the hydrazone and are two of the many unique features that allow for their programmed drug release. Their flexibility allows them to be relevant in a diverse range of applications, from anti-inflammatory to anticancer to acting as a chelating agent. This review paper discusses efficient ways to optimize the properties of hydrazones and their utilization in various clinical applications, including anticancer, anti-inflammatory, the prevention of platelet aggregation, and roles as chelating agents.

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Rajeev, Jain, Padmaja P., Gupta S., and Gupta Seema. "Electrochemical investigations on some hydrazones." Journal of Indian Chemical Society Vol. 77, Feb 2000 (2000): 91–93. https://doi.org/10.5281/zenodo.5862703.

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School of Studies in Chemistry, Jiwaji University, Gwalior-474 011, India <em>Manuscript received 10 November 1998, revised 2 August 1999, accepted 13 August 1999</em> The electrochemical behaviour of 3-(4'-sulphonamoyl)hydrazono-4-phenylaminobutane-2,4-drones has been studied over a wide pH range at dropping mercury and glassy carbon electrodes. These aryl hydrazones give one four-electron wave/peak corresponding to the reduction of hydrazono group. The wave/peak is found to be diffusion-controlled and irreversible in nature. A reduction mechanism is suggested for the aryl hydrazones.

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Pisk, Jana, Ivica Đilović, Tomica Hrenar, Danijela Cvijanović, Gordana Pavlović, and Višnja Vrdoljak. "Effective methods for the synthesis of hydrazones, quinazolines, and Schiff bases: reaction monitoring using a chemometric approach." RSC Advances 10, no. 63 (2020): 38566–77. http://dx.doi.org/10.1039/d0ra06845d.

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Patra, Debashis, Subhabrata Paul, Indira Majumder та ін. "Exploring the effect of substituent in the hydrazone ligand of a family of μ-oxidodivanadium(v) hydrazone complexes on structure, DNA binding and anticancer activity". Dalton Transactions 46, № 46 (2017): 16276–93. http://dx.doi.org/10.1039/c7dt03585c.

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Kpoviessi, Bénédicta Kpadonou, Bardieu Atchadé, Basile Goueti, et al. "Synthesis, Spectrometrical Characterization and Pharmacological Properties of Six Substituted Hydrazones with Carbonyl Compounds." Chemical Science International Journal 34, no. 2 (2025): 11–24. https://doi.org/10.9734/csji/2025/v34i2953.

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Hydrazones are molecules that prevent the growth of several microbial and parasitic strains by inhibited the replication of DNA sequences due to their chelating properties of metal ions. They are well recognized for Antiparasitic, Antimicrobial, Antibacterial, Antiviral, Antitumoral, Antimalarial and Anticonvulsive activities. The aim of the current study is to synthesized novel substituted hydrazones of ketones and aromatic aldehydes and to study their antiparasitic activities against Trypanosoma brucei brucei parasite. Synthesized hydrazone derivatives have been confirmed by elemental analysis and HPLC method, SMHR, 1H and 13C NMR spectroscopy. Three hydrazones derivatives have been synthesized namely phenylhydrazones, 2,4-dinitrophenyl hydrazones and benzohydrazones. The antiparasitic properties of these molecules were evaluated on Trypanosoma brucei brucei. The derivatives from phenylhydrazones and benzohydrazones were showing more antiparasitic activity like benzophenone benzohydrazone (D3) and salicylaldehyde phenylhydrazone (B1) compounds, which exhibited moderate activity on Trypanosoma brucei brucei (IC50 = 19.49 μM; IC50 = 20.01 μM respectively). Cytotoxicity tests again the human noncancer fibroblast cell line (WI38) were carried out with selected synthesized compounds and it showed that the most compounds were active against Trypanosoma brucei brucei. As a result of these findings, hydrazones could be a promising route in the treatment of trypanosomiasis.

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Fazylov, S., O. Nurkenov, I. Pustolaikina, et al. "CLATHRATE COMPLEXES OF HYDRAZONES OF 2- AND 4-HYDROXYBENZOIC ACIDS WITH CYCLODEXTRINS AND THEIR PROPERTIES." Chemical Journal of Kazakhstan, no. 1 (March 27, 2025): 25–36. https://doi.org/10.51580/2025-1.2710-1185.03.

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The paper presents the results of a study on the preparation of water-soluble complexes of inclusions of 4- and 2-hydroxyhydrazides of benzoic acid and their hydrazones with cyclodextrins (β-CD, γ-CD) in an aqueous alcohol solution. Methods. The complexation of the obtained hydrazones with --, -, -cyclodextrins was studied in silico using molecular docking and modeling methods. Results and discussion. All the investigated hydrazones demonstrated the best value of binding affinity with β -cyclodextrin. The efficiency of binding of the studied hydrazones to cyclodectrins is provided primarily by the correspondence of the geometric parameters of the "guest" and "host" molecules, as well as the formation of intermolecular hydrogen bonds. The complexation of the studied cγ-CD hydrazones proceeds with the participation of both internal protons of the cyclodextrin cavity and those located on the outer surface of the conical cone to form mixed supramolecular complexes. The spectral and thermochemical properties of the inclusion complexes were characterized using IR, 1H, and 13C NMR spectroscopy. Conclusion. The optimal conditions proposed in the work for the encapsulation of hydrazone derivatives of benzoic acid can be used in the preparation of water-soluble forms of similar compounds.

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Dinda, Soumitra, Tamanna Sultana, Suhana Sultana, et al. "Ruthenocycles of benzothiazolyl and pyridyl hydrazones with ancillary PAHs: synthesis, structure, electrochemistry and antimicrobial activity." New Journal of Chemistry 44, no. 26 (2020): 11022–34. http://dx.doi.org/10.1039/d0nj01447h.

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The antimicrobial activity of ruthenocycles of pyridyl and benzothiazolyl hydrazones has been investigated. The study established that such activity is comparatively higher for the complex containing benzothiazolyl hydrazone.

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Zhu, Xu, and Shunsuke Chiba. "TEMPO-mediated allylic C–H amination with hydrazones." Org. Biomol. Chem. 12, no. 26 (2014): 4567–70. http://dx.doi.org/10.1039/c4ob00839a.

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TEMPO-mediated reactions of alkenyl hydrazones afforded azaheterocycles via sp<sup>3</sup> C–H allylic amination. The transformation is featured by a sequence of remote allylic H-radical shift and allylic homolytic substitution with hydrazone radicals.

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Vojinovic-Jesic, Ljiljana, Sladjana Novakovic, Vukadin Leovac, and Valerija Cesljevic. "Transition metal complexes with Girard reagents and their hydrazones." Journal of the Serbian Chemical Society 77, no. 9 (2012): 1129–55. http://dx.doi.org/10.2298/jsc120704083v.

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This is the first review dealing with the coordination chemistry of metal complexes with Girard's reagents and their hydrazones. The short introduction points out to chemical properties and significance of these organic compounds. The next section briefly describes synthetic methods for preparing complexes with Girard's reagents, as well as modes of coordination of these ligands. The last two extensive sections review the preparation, stereochemistry and structural characteristics of metal complexes with Girard's hydrazones, including some newer non-hydrazonic derivatives of Girard's reagents, also.

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Kandil, Farouk, Mohamad Khaled Chebani, and Wail Al Zoubi. "Synthesis of Macrocyclic Bis-Hydrazone and Their Use in Metal Cations Extraction." ISRN Organic Chemistry 2012 (February 8, 2012): 1–8. http://dx.doi.org/10.5402/2012/208284.

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Two new macrocyclic hydrazone Schiff bases were synthesized by reaction of succindihydrazide and adipdihydrazide with acetylacetone. Hydrazones have been characterized by elemental analyses and IR, mass, 1H NMR, and 13C NMR spectral data. Hydrazones have been studied by liquid-liquid extraction towards the s-metal ions (Li+, Na+, and K+) and d-metal ions (Cu2+ and Cr3+) from aqueous phase to organic phase. The effect of chloroform and dichloromethane as organic solvents over the metal chlorides extraction was investigated at 25 ± 0.1°C by using flame atomic absorption. We found differences between the two solvents in extraction selectivity.

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Popiołek, Łukasz. "Updated Information on Antimicrobial Activity of Hydrazide–Hydrazones." International Journal of Molecular Sciences 22, no. 17 (2021): 9389. http://dx.doi.org/10.3390/ijms22179389.

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Hydrazide–hydrazones possess a wide spectrum of bioactivity, including antibacterial, antitubercular, antifungal, anticancer, anti-inflammatory, anticonvulsant, antidepressant, antiviral, and antiprotozoal properties. This review is focused on the latest scientific reports regarding antibacterial, antimycobacterial, and antifungal activities of hydrazide–hydrazones published between 2017 and 2021. The molecules and their chemical structures presented in this article are the most active derivatives, with discussed activities having a hydrazide–hydrazone moiety as the main scaffold or as a side chain. Presented information constitute a concise summary, which may be used as a practical guide for further design of new molecules with antimicrobial activity.

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Al Nasr, Ibrahim S., Waleed S. Koko, Tariq A. Khan, Rainer Schobert, and Bernhard Biersack. "Old Dogs with New Tricks: Antiparasitic Potential of Structurally Diverse 5-Nitrofuran and 5-Nitrothiophene Imines and Acyl Hydrazones." Scientia Pharmaceutica 91, no. 3 (2023): 44. http://dx.doi.org/10.3390/scipharm91030044.

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Miscellaneous imines and acyl hydrazones were prepared from 5-nitrofuraldehyde and 5-nitrothiophene-2-carboxaldehyde. Their activities against Toxoplasma gondii and Leishmania major parasites were evaluated. Promising antiparasitic effects and selectivities were observed for certain acyl hydrazones and imines. Cobalt(II) and copper(II) complexes conserved the high anti-Toxoplasma activities of 3-hydroxy-2-naphthoic carboxyl hydrazone (2a). In addition, sound activities against L. major promastigotes were observed for various analogs of 2a (2b and 2i) and pyrid-2-ylpyrazole-based imines (3g and 3h). Relatively low toxicities to kidney cells and macrophages indicate promising selectivity profiles for these compounds.

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Pangal, Anees, Javed A. Shaikh, Mansura Mulani, and Khursheed Ahmed. "SYNTHESIS, ANTICANCER ACTIVITIES AND IN SILICO SCREENING OF 3-ACETYLCOUMARINHYDRAZONE SCAFFOLDS." Journal of Advanced Scientific Research 12, no. 04 Suppl 1 (2021): 225–33. http://dx.doi.org/10.55218/jasr.s1202112425.

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3-acetylcoumarin hydrazone scaffolds, synthesized from 3-acetylcoumarin and substituted benzoic acid hydrazides are reported with structural characterization using IR, HRMS, 1H and 13C-NMR. The In vitro anticancer activities against three human cancer cell lines viz. MCF-7 (human breast cancer cell line), HeLa (human cervical cancer cell line) and SCC-40 (human oral squamous cell carcinoma) are carried out while the tumour selectivity of compounds are tested on the normal human peripheral blood mononuclear cells (PBMCs). The compounds 3ACOH, 3ACDH and 3ACMH exhibited higher sensitivity towards HeLa with GI50 values between 20.4 - 44.1μg/ml and this range of GI50 concentration of hydrazones showed no remarkable toxicity against normal PBMCs. Molecular docking studies revealed commendable binding interactions with cyclooxygenase enzyme (PDB ID 6COX). ADMET analysis shows the hydrazones are showing drug-likeness properties. The reported observations of 3-acetylcoumarin hydrazones suggest their possible role as promising new anticancer drug candidates.

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Zahirović, Adnan, Irnesa Osmanković, Amar Osmanović, et al. "Interaction of Copper(II) Complexes of Bidentate Benzaldehyde Nicotinic Acid Hydrazones with BSA: Spectrofluorimetric and Molecular Docking Approach." Acta Chimica Slovenica 70, no. 1 (2023): 74–85. http://dx.doi.org/10.17344/acsi.2022.7826.

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Two copper(II) complexes of 4-chloro- and 4-dimethylaminobenzaldehyde nicotinic acid hydrazones were prepared and characterized by elemental analysis, mass spectrometry, infrared and electron spectroscopy and conductometry. These rare examples of bis(hydrazonato)copper(II) complexes are neutral complex species with copper(II) center coordinated with two monoanionic bidentate O,N-donor hydrazone ligands coordinated in enol-imine form. The interaction of hydrazone ligands and corresponding copper(II) complexes with CT DNA and BSA was investigated. Copper(II) complexes are slightly effective in binding the DNA than pristine hydrazones. The results indicate groove binding or moderate intercalation which are not significantly affected by the nature of substituent at hydrazone ligands. On contrary, affinities of two copper(II) complexes toward BSA significantly differs and depends on the nature of the substituent, however in absence of thermodynamic data difference in nature of binding forces cannot be excluded. The complex bearing electron- withdrawing 4-chloro substituent has larger affinity toward BSA compared to 4-dimethyamino analogue. These findings were theoretically supported by molecular docking study.

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Sun, Zi-Qiang, Shun-Feng Yu, Xin-Lan Xu, Xiao-Yang Qiu, and Shu-Juan Liu. "Two Vanadium(V) Complexes Derived from Bromo and Chloro-Substituted Hydrazone Ligands: Syntheses, Crystal Structures and Antimicrobial Property." Acta Chimica Slovenica 67, no. 4 (2020): 1281–89. http://dx.doi.org/10.17344/acsi.2020.6236.

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Two vanadium(V) complexes derived from the bromo and chloro-substituted hydrazones N’-(4-bromo-2-hydroxybenzylidene)- 2-chlorobenzohydrazide (H2L1) and N’-(3-bromo-5-chloro-2-hydroxybenzylidene)-3-methylbenzohydrazide (H2L2) with the formula [VOL1(OCH3)(CH3OH)] (1) and [VOL2(OCH3)(CH3OH)] (2) were newly synthesized and characterized by IR, UV-Vis and 1H NMR spectroscopy. The structures of H2L1 and the complexes were further confirmed by single crystal X-ray diffraction. Both vanadium complexes are mononuclear, with the metal atoms coordinated by the hydrazone ligands, methanol ligands, and methanolate ligands, and the oxo groups, forming octahedral geometry. The hydrazones and the vanadium complexes were assayed for the antimicrobial activities on Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Pseudomonas fluorescence, and the fungi Candida albicans and Aspergillus niger. The existence of the bromo and chloro groups in the hydrazone ligands may improve the antimicrobial property.

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Li, Chao-Jun, Jianlin Huang, Xi-Jie Dai, et al. "An Old Dog with New Tricks: Enjoin Wolff–Kishner Reduction for Alcohol Deoxygenation and C–C Bond Formations." Synlett 30, no. 13 (2019): 1508–24. http://dx.doi.org/10.1055/s-0037-1611853.

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The Wolff–Kishner reduction, discovered in the early 1910s, is a fundamental and effective tool to convert carbonyls into methylenes via deoxygenation under strongly basic conditions. For over a century, numerous valuable chemical products have been synthesized by this classical method. The reaction proceeds via the reversible formation of hydrazone followed by deprotonation with the strong base to give an N-anionic intermediate, which affords the deoxygenation product upon denitrogenation and protonation. By examining the mechanistic pathway of this century old classical carbonyl deoxygenation, we envisioned and subsequently developed two unprecedented new types of chemical transformations: a) alcohol deoxygenation and b) C–C bond formations with various electrophiles including Grignard-type reaction, conjugate addition, olefination, and diverse cross-coupling reactions.1 Introduction2 Background3 Alcohol Deoxygenation3.1 Ir-Catalyzed Alcohol Deoxygenation3.2 Ru-Catalyzed Alcohol Deoxygenation3.3 Mn-Catalyzed Alcohol Deoxygenation4 Grignard-Type Reactions4.1 Ru-Catalyzed Addition of Hydrazones with Aldehydes and Ketones4.2 Ru-Catalyzed Addition of Hydrazone with Imines4.3 Ru-Catalyzed Addition of Hydrazone with CO2 4.4 Fe-Catalyzed Addition of Hydrazones5 Conjugate Addition Reactions5.1 Ru-Catalyzed Conjugate Addition Reactions5.2 Fe-Catalyzed Conjugate Addition Reactions6 Cross-Coupling Reactions6.1 Ni-Catalyzed Negishi-type Coupling6.2 Pd-Catalyzed Tsuji–Trost Alkylation Reaction7 Other Reactions7.1 Olefination7.2 Heck-Type Reaction7.3 Ullmann-Type Reaction8 Conclusion and Outlook

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El-Azab, Adel S., Alaa A. M. Abdel-Aziz, Ahmed H. Bakheit, et al. "Remarkable utilization of quinazoline-based homosulfonamide for in vitro cytotoxic effects with triple kinase inhibition activities: cell cycle analysis and molecular docking profile." RSC Advances 15, no. 1 (2025): 541–58. https://doi.org/10.1039/d4ra07174c.

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Hydrazone 5 had a higher mean GI50 (1.1 μM) than gefitinib and erlotinib (2.1 and 7.7 μM). Compared to gefitinib and dinaciclib, hydrazones 5 and 6 strongly inhibit EGFR, HER2, and CDK9 kinases. They are also less toxic to WI-38 than doxorubicin.

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Harjeet, Kaur, Manpreet, and Shilpa. "Review on hydrazone and it's biological activities." International Journal of Multidisciplinary Research Transactions 6, no. 4 (2024): 166–81. https://doi.org/10.5281/zenodo.11075191.

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The main traits and attributes of hydrazone are enumerated in its abstract. The chemical compound hydrazone is composed of a particular functional group known as the hydrazone group (-NHN=). Numerous biological activities, such as antibacterial, antiviral, antioxidant, and anticancer properties, are well-known for it. Because of these properties, hydrazone molecules are attractive options for a range of medical and pharmaceutical applications. However, hydrazones' particular biological activity can differ based on their chemical makeup and alterations. To completely comprehend their methods of action and their therapeutic applications, more research is required.

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Costa, Maximilian, Frances Adhamidhi, Maxim Mastyugin, et al. "Solvent- and Catalyst-Free Environmentally Benign High Hydrostatic Pressure-Assisted Synthesis of Bioactive Hydrazones and the Evaluation of Their Stability Under Various Storage Conditions." Molecules 29, no. 22 (2024): 5287. http://dx.doi.org/10.3390/molecules29225287.

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Our group has seen great promise in using substituted diaryl-hydrazones to alleviate oxidative stress in preeclampsia. Specifically, fluorinated diaryl-hydrazones have shown great efficacy, confirmed via antioxidant assays and animal trials using pregnant mice. In addition to efficient antioxidant properties, these diaryl-hydrazones are also considered non-toxic. While the synthesis of these compounds is relatively simple, it commonly utilizes undesirable solvents and glacial acetic acid as the catalyst; additional solvents are needed for the isolation of the desired products, which negatively affects the green synthesis of the hydrazones. To combat this possible industrial roadblock, we have begun incorporating the use of hydrostatic high pressure (HHP) in the synthesis. The use of HHP allowed us to synthesize substituted diaryl-hydrazones in a 1:1 molar ratio without the need for solvents or acid catalysts. The optimized procedure can produce nearly quantitative yields, leading to an easier isolation of the products. Different HHP methodologies, such as constant high-pressure treatment and cycling (with different number of cycles, holding and decompression times) were applied and cycling was observed to be the most efficient activation for the majority of the reactions. Stability experiments were also conducted with one of the products and observed that although the solid-state storage does not alter the hydrazone, storing it in various solvents may significantly decrease the concentration of the active component which should be considered when performing the biochemical/biological assays.

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Kaur, Aneet Kamal, Renu Bala, Poonam Kumari, Sumit Sood, and Karan Singh. "Microwave Assisted Vilsmeier-Haack Reaction on Substituted Cyclohexanone Hydrazones: Synthesis of Novel 4,5,6,7-Tetrahydroindazole Derivatives." Letters in Organic Chemistry 16, no. 3 (2019): 170–75. http://dx.doi.org/10.2174/1570178615666180917101637.

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Vilsmeier-Haack reaction is one of the most important chemical reactions used for formylation of electron-rich arens. Even though Vilsmeier-Haack reaction was studied on a wide variety of hydrazones of enolizable ketones, literature lacks the examples of the use of 4-substituted cyclohexanones as a substrate. The cyclization potential of hydrazones of cyclic keto compounds is still interested topic of investigation. In the present study, the reaction of various hydrazines with 4-substituted cyclohexanones was proceeded and the resulted hydrazones in crude form were treated with Vilsmeier- Haack reagent using both conventional as well as microwave methods. The reaction of phenyl hydrazine with 4-phenylcyclohexanone yielded the corresponding tetrahydro-1H-carbazole instead of hydrazone during solvent evaporation at 40ºC. By keeping the temperature of water bath to 0ºC, the corresponding hydrazone was isolated in crude form which was immediate treated with POCl3/DMF for 10 min at 90ºC using microwave irradiation method afforded novel 4,5,6,7-tetrahydroindazole derivative. Using this optimized condition, the substrate scope for the synthesis of tetrahydroindazole derivatives was explored and synthesized total 6 final compounds. The microwave assisted synthesis of tetrahydroindazoles from 4-substituted cyclohexanones has been reported for the first time under mild conditions in good yield. Easy work up procedure, high yielding, shortened reaction times, clean and ecofriendly are the main advantages of this protocol.

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KASIMBI, D., K. HUSSAIN REDDY, and N. DEVANNA. "Synthesis, Spectral Characterization and Antibacterial Activity of Copper(II) Complexes of Functionalized Hydrazones." Asian Journal of Chemistry 31, no. 6 (2019): 1289–93. http://dx.doi.org/10.14233/ajchem.2019.21942.

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Copper(II) complexes having the formula CuL2 {where, L = 2-acetylthiophene acetoylhydrazone (ATAH), 2-acetylthiophene benzoylhydrazone (ATBH)} have been investigated on the basis of elemental analysis, molar conductivity measurements, magnetic susceptibility, UV-visible, IR and ESR spectral data. Non-electrolytic nature of the complexes are revealed by molar conductance data. IR spectral data suggested that hydrazones act as tridentate ligands. The spin Hamiltonian, orbital reduction and bonding parameters of complexes are calculated using ESR spectra of complexes. The compounds are screened for their antibacterial activities against Pseudomonas aureoginos and Bacillus cereus. Acetoylhydrazones show more antibacterial activity than the corresponding benzoyl hydrazones. Some of the Cu(II) complexes show more activity than hydrazone ligands.

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Enders, Dieter, and Christoph Thiebes. "Efficient stereoselective syntheses of piperidine, pyrrolidine, and indolizidine alkaloids." Pure and Applied Chemistry 73, no. 3 (2001): 573–78. http://dx.doi.org/10.1351/pac200173030573.

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Recent advances in the diastereo- and enantioselective synthesis of piperidine, pyrrolidine, and indolizidine alkaloids, based on the highly stereoselective 1,2-addition to the CN double bond of chiral aldehyde-SAMP/RAMP hydrazones, are described. The enantioselective syntheses of the pyrrolidine alkaloids bgugaine and (2S,12¢R)-2-(12¢-aminotridecyl)-pyrrolidine, a defense alkaloid of the Mexican bean beetle are reported. Furthermore, the SAMP/RAMP-hydrazone method was applied to the syntheses of two 5,8-disubstituted indolizidine alkaloids that have been extracted from neotropical poison-dart frogs. The a-alkylation of aldehyde-SAMP/RAMP hydrazones has been used in the enantioselective synthesis of two epimers of stenusine, a 3-substituted piperidine alkaloid and spreading reagent of the beetle Stenus comma.

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30

Nocheva, Hristina, Stanislava Vladimirova, Diana Tzankova, Lily Peikova, and Maya Georgieva. "Analgesic properties of newly synthesized N pyrrolyl hydrazide hydrazones." Tropical Journal of Pharmaceutical Research 22, no. 1 (2023): 121–27. http://dx.doi.org/10.4314/tjpr.v22i1.17.

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Purpose: To screen a series of newly synthesized N-pyrrolyl hydrazide hydrazones for analgesic activity via Paw-pressure (PP) test and hot plate test (HPT). Methods: The compounds newly synthesized through the classical Paal-Knor cyclization, N-pyrrolyl hydrazide-hydrazones were administered intraperitoneally at a dose of 20 mg/kg. Paw pressure and hot plate tests were applied to assess the analgesic properties. In addition, stress-induced analgesia with naloxone as a non-selective opioid receptor antagonist was performed. Results: The compound (DI-5g), containing an izatine carbonyl fragment, was the most promising. It presented the highest paw pressure threshold (25 AU at 30th min) by exceeding the analgesic activity of the referent metamizole (23 AU at 30th min). The relative effect from the hot plate test was consistent with the paw pressure results. Opioid receptors were involved in the analgesic activities of N-pyrrolyl hydrazide-hydrazones. Conclusion: The N-pyrrolyl carboxylic acids are synthesized and identified as new compounds and their hydrazide-hydrazone derivatives as promising leads for future design and synthesis of drugs with possibly prolonged analgesic activity.

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Çıkla-Süzgün, Pelin, and Ş. Güniz Küçükgüzel. "Recent Advances in Apoptosis: THE Role of Hydrazones." Mini-Reviews in Medicinal Chemistry 19, no. 17 (2019): 1427–42. http://dx.doi.org/10.2174/1389557519666190410125910.

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: The process of programmed cell death in higher eukaryotes (apoptosis), is generally characterized by distinct morphological characteristics and energy-dependent biochemical mechanisms. Apoptosis is considered as a vital component of various processes including normal cell turnover, proper development and functioning of the immune system, hormone-dependent atrophy, embryonic development and chemical-induced cell death. Apoptosis seems to play an important key role in the progression of several human diseases like Alzheimer's disease, Parkinson's disease and many types of cancer. Promotion of apoptosis may be a good approach for the prevention of cancer cell proliferation. In early studies, antitumor compounds have been found to induce the apoptotic process in tumor cells. On the other hand, several hydrazones were reported to have lower toxicity than hydrazides due to the blockage of –NH2 group. Therefore, the design of hydrazones that activate and promote apoptosis is an attractive strategy for the discovery and development of potential anticancer agents. The aim of this review is to provide a general overview of current knowledge and the connection between apoptosis and hydrazone. It is also the guide for the apoptotic activities of new hydrazone derivatives.

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32

Hamed, Atef A., Hesham F. Bader, and El-Sayed H. El-Ashry. "4′, x-Seco And 4′,x-4′,5′-Diseco C-Nucleosides From 2-Hydrazino-(3H)- Thieno [2,3-D] Pyrimidin-4-Ones." Zeitschrift für Naturforschung B 56, no. 8 (2001): 826–36. http://dx.doi.org/10.1515/znb-2001-0817.

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Cyclization of 2-hydrazino-5,6-dimethyl-3H-thieno[2,3-d]pyrimidin-4-one (1) with acetic acid gave 3,6,7-trimethyl-l,2,4-triazolo[3,4-a]thieno[2,3-d] pyrimidin-5-one (5) whose Dimroth rearrangement gave 2,6,7-trimethyl-l,2,4-triazolo[3,4-a]thieno[2,3-d]pyrimidin-5-one (11). Alternatively, 5 was obtained from the dehydrogenative cyclization of acetaldehyde 5,6- dimethyl-4-3H-oxo-thieno[2,3-d]pyrimidin-2-yl hydrazone (7). Reaction of 1 and 2 with a number of sugars gave the respective hydrazones 19 and 20. Those of the D-glucose exist in the cyclic pyranosyl structure in addition to minor amounts of the acyclic structure. Dehydrogenative cyclization of the sugar hydrazones gave the respective fused tricyclic compounds 25 and 26

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33

Chandrasekhar, Vadapalli, Venkatasubbaiah Krishnan, Arunachalampillai Athimoolam, and Gurusamy Thangavelu Senthil Andavan. "New hybrid inorganic-organic polymers containing cyclophosphazenes as pendant groups: Cyclophosphazene ligands containing hydrazone linkages and their conversion to polymers." Canadian Journal of Chemistry 80, no. 11 (2002): 1415–20. http://dx.doi.org/10.1139/v02-099.

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The reaction of the cyclotriphosphazene N3P3Cl5[O-C6H4-p-C6H4-p-CH=CH2] (2) with 10 equiv of N-methylhydrazine proceeds in a regio-specific manner to afford the multi-functional hydrazide N3P3[N(Me)NH2]5[O- C6H4-p-C6H4-p-CH=CH2] (3). Condensation of 3 with o-hydroxy benzaldehyde or pyridine-2-carboxaldehyde affords the corresponding hydrazones N3P3[N(Me)N=CH-C6H4-o-OH]5[O-C6H4-p-C6H4-p-CH=CH2] (4) and N3P3[N(Me)N=CH-C6H4N]5[O-C6H4-p-C6H4-p-CH=CH2] (5), respectively. These hydrazones can be homopolymerized to afford polymers 6 and 7 containing multi-site coordinating cyclophosphazenes as pendant groups.Key words: cyclophosphazene, hydrazone, pendant polymers, hybrid polymers, polymeric ligands.

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34

Sarkar, Souvik, Asim A. Siddiqui, Shubhra J. Saha, et al. "Antimalarial Activity of Small-Molecule Benzothiazole Hydrazones." Antimicrobial Agents and Chemotherapy 60, no. 7 (2016): 4217–28. http://dx.doi.org/10.1128/aac.01575-15.

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ABSTRACTWe synthesized a new series of conjugated hydrazones that were found to be active against malaria parasitein vitro, as well asin vivoin a murine model. These hydrazones concentration-dependently chelated free iron and offered antimalarial activity. Upon screening of the synthesized hydrazones, compound 5f was found to be the most active iron chelator, as well as antiplasmodial. Compound 5f also interacted with free heme (KD[equilibrium dissociation constant] = 1.17 ± 0.8 μM), an iron-containing tetrapyrrole released after hemoglobin digestion by the parasite, and inhibited heme polymerization by parasite lysate. Structure-activity relationship studies indicated that a nitrogen- and sulfur-substituted five-membered aromatic ring present within the benzothiazole hydrazones might be responsible for their antimalarial activity. The dose-dependent antimalarial and heme polymerization inhibitory activities of the lead compound 5f were further validated by following [3H]hypoxanthine incorporation and hemozoin formation in parasite, respectively. It is worth mentioning that compound 5f exhibited antiplasmodial activityin vitroagainst a chloroquine/pyrimethamine-resistant strain ofPlasmodium falciparum(K1). We also evaluatedin vivoantimalarial activity of compound 5f in a murine model where a lethal multiple-drug-resistant strain ofPlasmodium yoeliiwas used to infect Swiss albino mice. Compound 5f significantly suppressed the growth of parasite, and the infected mice experienced longer life spans upon treatment with this compound. Duringin vitroandin vivotoxicity assays, compound 5f showed minimal alteration in biochemical and hematological parameters compared to control. In conclusion, we identified a new class of hydrazone with therapeutic potential against malaria.

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35

Silva, Laís Peres, Ivanilson Pimenta Santos, Dahara Keyse Carvalho Silva, et al. "Molecular Hybridization Strategy on the Design, Synthesis, and Structural Characterization of Ferrocene-N-acyl Hydrazones as Immunomodulatory Agents." Molecules 27, no. 23 (2022): 8343. http://dx.doi.org/10.3390/molecules27238343.

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Immunomodulatory agents are widely used for the treatment of immune-mediated diseases, but the range of side effects of the available drugs makes necessary the search for new immunomodulatory drugs. Here, we investigated the immunomodulatory activity of new ferrocenyl-N-acyl hydrazones derivatives (SintMed(141–156). The evaluated N-acyl hydrazones did not show cytotoxicity at the tested concentrations, presenting CC50 values greater than 50 µM. In addition, all ferrocenyl-N-acyl hydrazones modulated nitrite production in immortalized macrophages, showing inhibition values between 14.4% and 74.2%. By presenting a better activity profile, the ferrocenyl-N-acyl hydrazones SintMed149 and SintMed150 also had their cytotoxicity and anti-inflammatory effect evaluated in cultures of peritoneal macrophages. The molecules were not cytotoxic at any of the concentrations tested in peritoneal macrophages and were able to significantly reduce (p < 0.05) the production of nitrite, TNF-α, and IL-1β. Interestingly, both molecules significantly reduced the production of IL-2 and IFN-γ in cultured splenocytes activated with concanavalin A. Moreover, SintMed150 did not show signs of acute toxicity in animals treated with 50 or 100 mg/kg. Finally, we observed that ferrocenyl-N-acyl hydrazone SintMed150 at 100 mg/kg reduced the migration of neutrophils (44.6%) in an acute peritonitis model and increased animal survival by 20% in an LPS-induced endotoxic shock model. These findings suggest that such compounds have therapeutic potential to be used to treat diseases of inflammatory origin.

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36

Krátký, Martin, Katarína Svrčková, Quynh Anh Vu, Šárka Štěpánková, and Jarmila Vinšová. "Hydrazones of 4-(Trifluoromethyl)benzohydrazide as New Inhibitors of Acetyl- and Butyrylcholinesterase." Molecules 26, no. 4 (2021): 989. http://dx.doi.org/10.3390/molecules26040989.

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Based on the broad spectrum of biological activity of hydrazide–hydrazones, trifluoromethyl compounds, and clinical usage of cholinesterase inhibitors, we investigated hydrazones obtained from 4-(trifluoromethyl)benzohydrazide and various benzaldehydes or aliphatic ketones as potential inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). They were evaluated using Ellman’s spectrophotometric method. The hydrazide–hydrazones produced a dual inhibition of both cholinesterase enzymes with IC50 values of 46.8–137.7 µM and 19.1–881.1 µM for AChE and BuChE, respectively. The majority of the compounds were stronger inhibitors of AChE; four of them (2-bromobenzaldehyde, 3-(trifluoromethyl)benzaldehyde, cyclohexanone, and camphor-based 2o, 2p, 3c, and 3d, respectively) produced a balanced inhibition of the enzymes and only 2-chloro/trifluoromethyl benzylidene derivatives 2d and 2q were found to be more potent inhibitors of BuChE. 4-(Trifluoromethyl)-N’-[4-(trifluoromethyl)benzylidene]benzohydrazide 2l produced the strongest inhibition of AChE via mixed-type inhibition determined experimentally. Structure–activity relationships were identified. The compounds fit physicochemical space for targeting central nervous systems with no apparent cytotoxicity for eukaryotic cell line together. The study provides new insights into this CF3-hydrazide–hydrazone scaffold.

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37

Pogonin, Aleksandr E., George A. Gamov, Maksim N. Zavalishin, and Valentin A. Sharnin. "CONFORMATIONAL BEHAVIOR OF HYDRAZONE DERIVED FROM PYRIDOXAL 5’-PHOSPHATE AND ISONIAZID." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENIY KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 61, no. 12 (2018): 101–7. http://dx.doi.org/10.6060/ivkkt.20186112.5846.

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The hydrazones derived from pyridoxal or pyridoxal 5’-phosphate and heterocyclic hydrazides are of interest due to their potential biological activity and metal sensing properties. These characteristics of hydrazones could be dependent on the conformation equilibria of molecule since the most stable conformer could differ from the one with the highest affinity towards biomolecule or metal ion. In the present contribution, deprotonated hydrazone formed by pyridoxal 5’-phosphate and isoniazid (PLP-INH3-) was studied by means of quantum chemistry. Three rotations leading to eight conformers are possible for this hydrazone; however, four of those species obtained by rotation of pyridine ring of isoniazid residue are degenerated. The geometry of different non-degenerated rotation conformers of the hydrazine (differing by the mutual arrangement of carbonyl group of the isoniazid residue and oxygen in 3’-site of PLP moiety) was optimized using density functional theory (B3LYP/6-311++G(d,p)). Activation barriers were evaluated. Changes in energy and geometry of conformers as well as transition states are discussed. Quantitative QTAIM (Quantum Theory of Atoms in Molecules) analysis was performed in order to check the intermolecular hydrogen bonding existence. The species capable of forming the complex with the metal ions differs from the most stable (according to the total energy values) conformer. The preliminary prediction of biological activity of PLP-INH3- hydrazone and the docking for the hydrazone and G-protein-coupled receptor kinase were performed and the preferable conformation for ligand binding to the kinase active site was found.

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38

Dammene Debbih, Ouafa, Assia Sid, Rafika Bouchene, Sofiane Bouacida, Wissam Mazouz, and Noureddine Gherraf. "Two hydrazones derived from 1-aryl-3-(p-substituted phenyl)prop-2-en-1-one: synthesis, crystal structure, Hirshfeld surface analysis andin vitrobiological properties." Acta Crystallographica Section C Structural Chemistry 74, no. 6 (2018): 703–14. http://dx.doi.org/10.1107/s2053229618006812.

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Two chalcones were synthesized by the aldolic condensation of enolizable aromatic ketones with substituted benzaldehydes under Claisen–Schmidt reaction conditions and then treated with 2,4-dinitrophenylhydrazine to yield their corresponding hydrazones. The two (E,Z)-2,4-dinitrophenylhydrazone structures, namely (Z)-1-(2,4-dinitrophenyl)-2-[(E)-3-(4-methylphenyl)-1-phenylallylidene]hydrazine, C22H18N4O4, (H1), and (Z)-1-[(E)-3-(4-chlorophenyl)-1-(naphthalen-1-yl)allylidene]-2-(2,4-dinitrophenyl)hydrazine, C25H17ClN4O4, (H2), were isolated by recrystallization and characterized by FT–IR, UV–Vis, single-crystal and powder X-ray diffraction methods. The UV–Vis spectra of the hydrazones have been studied in two organic solvents of different polarity. It was found that (H2) has a molar extinction coefficient larger than 40000. Single-crystal X-ray diffraction analysis reveals that the molecular zigzag chains of (H1) and (H2) are interconnected through noncovalent contacts. A quantitative analysis of the intermolecular interactions in the crystal structures has been performed using Hirshfeld surface analysis. All the synthesized chalcones and hydrazones were evaluated for their antibacterial and antioxidant activities. Results indicate that the studied compounds show significant activity against Gram negativeEscherichia colistrain and the chalcone 3-(4-methylphenyl)-1-phenylprop-2-en-1-one, (C1), was the most effective. In addition, only hydrazone (H1) displayed a moderate DPPH (2,2-diphenyl-1-picryl hydrazyl) scavenging efficiency.

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39

Kapusterynska, Anna, Christian Bijani, Damian Paliwoda, et al. "Mechanochemical Studies on Coupling of Hydrazines and Hydrazine Amides with Phenolic and Furanyl Aldehydes—Hydrazones with Antileishmanial and Antibacterial Activities." Molecules 28, no. 13 (2023): 5284. http://dx.doi.org/10.3390/molecules28135284.

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Hydrazone compounds represent an important area of research that includes, among others, synthetic approaches and biological studies. A series of 17 hydrazones have been synthesized by mechanochemical means. The fragments chosen were phenolic and furanyl aldehydes coupled with 12 heterocyclic hydrazines or hydrazinamides. All compounds can be obtained quantitatively when operating on a planetary ball mill and a maximum reaction time of 180 min (6 cycles of 30 min each). Complete spectroscopic analyses of hydrazones revealed eight compounds (3–5, 8–11, 16) present in one geometric form, six compounds (1, 2, 13–15) present in two isomeric forms, and three compounds (6, 7, 12) where one rotation is restricted giving rise to two different forms. The single crystal X-ray structure of one of the hydrazones bearing the isoniazid fragment (8) indicates a crystal lattice consisting of two symmetry-independent molecules with different geometries. All compounds obtained were tested for anti-infectious and antibacterial activities. Four compounds (1, 3, 5 and 8) showed good activity against Mycobacterium tuberculosis, and one (7) was very potent against Staphylococcus aureus. Most interesting, this series of compounds displayed very promising antileishmanial activity. Among all, compound 9 exhibited an IC50 value of 0.3 µM on the Leishmania donovani intramacrophage amastigote in vitro model and a good selectivity index, better than miltefosine, making it worth evaluating in vivo.

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40

Shah, Muhammad Abdullah, Ala Uddin, Muhammad Raza Shah, et al. "Synthesis and Characterization of Novel Hydrazone Derivatives of Isonicotinic Hydrazide and Their Evaluation for Antibacterial and Cytotoxic Potential." Molecules 27, no. 19 (2022): 6770. http://dx.doi.org/10.3390/molecules27196770.

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Hydrazones are active compounds having an azomethine –NHN=CH group and are widely studied owing to their ease of preparation and diverse pharmacological benefits. Novel isonicotinic hydrazone derivatives of vanillin aldehyde and salicyl aldehyde were synthesized that had azomethine linkages and were characterized by UV–Visible, FTIR, EI-MS, 1H-NMR and 13C-NMR spectroscopy. The compounds were screened for their antibacterial activity against Staphylococcus aureus, Bacillus subtilus, and Escherichia coli using disc diffusion and minimum inhibitory concentration (MIC) methods. For cytotoxicity, a brine shrimp lethality test was performed to calculate the lethal concentration (LC50). The results demonstrated appreciable antibacterial activities against the applied strains, amongst which the compounds coded NH3 and NH5 showed maximum inhibition and MIC responses. In terms of cytotoxic activity, the maximum effect was observed in compound NH5 and NH6 treatments with minimum survival percentages of 36.10 ± 3.45 and 32.44 ± 2.0, respectively. These hydrazones could be potential candidates in antitumorigenic therapy against various human cancer cells.

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41

Siemann, Stefan, Darryl P. Evanoff, Laura Marrone, Anthony J. Clarke, Thammaiah Viswanatha та Gary I. Dmitrienko. "N-Arylsulfonyl Hydrazones as Inhibitors of IMP-1 Metallo-β-Lactamase". Antimicrobial Agents and Chemotherapy 46, № 8 (2002): 2450–57. http://dx.doi.org/10.1128/aac.46.8.2450-2457.2002.

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ABSTRACT Members of a family of N-arylsulfonyl hydrazones have been identified as novel inhibitors of IMP-1, a metallo-β-lactamase of increasing prevalence. Structure-activity relationship studies have indicated a requirement for bulky aromatic substituents on each side of the sulfonyl hydrazone backbone for these compounds to serve as efficient inhibitors of IMP-1. Molecular modeling has provided insight into the structural basis for the anti-metallo-β-lactamase activity exhibited by this class of compounds.

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42

ANENKO, D. S., P. S. BOBROV, I. L. ABISALOVA, G. A. SUBOCH, E. O. SERGEEVA, and T. N. GLIZHOVA. "ANTIOXIDANT ACTIVITY OF QUINOXALYL HYDRAZONES OF 2-HYDROXYIMINO-1,3-DICARBONYL COMPOUNDS." Chemistry for Sustainable Development 31, no. 4 (2023): 349–53. http://dx.doi.org/10.15372/csd2023477.

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Biosimilarity and pharmacokinetic descriptors were obtained using SwissADME and ADMETlab 2.0 web services. Analysis of the obtained descriptors shows that, according to Lipinski’s rule, quinoxalyl hydrazones of 2-hydroximino-1,3-dioxocompounds may be promising candidates for drug development for oral administration. Analysis of the pharmacokinetic descriptors of the structures studied shows that, according to the in silico predictions, the compounds can penetrate the blood-brain barrier, be absorbed in the gastrointestinal tract, bind to plasma proteins, be rapidly eliminated from target cells and inhibit CYP3A4, CYP1A2, CYP2C19 and CYP2D6 isoenzymes. The antioxidant activity of quinoxalyl hydrazone derivatives with different benzoyl, ester and acetyl moieties has been studied. Pharmacological screening of the obtained compounds was performed in vitro in the model of Fe2+-induced lipid peroxidation. The data of pharmacological screening indicate clearly pronounced inhibition of lipid peroxidation in the system of yolk lipoproteins by the compounds obtained, which indicates a significant contribution of quinoxalone scaffold in the manifestation of antioxidant properties. Variations in the structure of the starting 1,3-dicarbonyl compounds did not result in significant changes in the antioxidant activity of the obtained hydrazones. The compounds obtained can be promising compounds with marked antioxidant activity for further in vivo studies, including investigation of acute and chronic toxicity. The leading compound is tolyl-substituted quinoxalyl hydrazone IIb

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43

Suvarapu, Lakshmi Narayana, Young Kyo Seo, Sung-Ok Baek, and Varada Reddy Ammireddy. "Review on Analytical and Biological Applications of Hydrazones and their Metal Complexes." E-Journal of Chemistry 9, no. 3 (2012): 1288–304. http://dx.doi.org/10.1155/2012/534617.

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Hydrazones are very important group of analytical regents for the determination of various metal ions by using various analytical techniques. Besides this use of hydrazones are also having biological activities also. In this paper we first discussed about the chemical nature of hydrazones and their biological activities. We mainly focused on the papers which were published during 1980-2011 on analytical applications (spectrophotometric and spectrofluorimetric) of hydrazones. We gave the total established conditions for the determination of various metal ions with hydrazones.

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44

Kasimbi, D., K. Hussain Reddy, and N. Devanna. "Synthesis, Spectral Characterization and Antibacterial Activity of Functionalized Hydrazones." Oriental Journal of Chemistry 35, no. 2 (2019): 557–62. http://dx.doi.org/10.13005/ojc/350208.

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New hydrazones have been synthesized by condensing 2-acetylthiophene with acetic hydrazide and benzhydrazide. The synthesized hydrazones viz. 2-acetylthiophene acetoylhydrazone (ATAH), 2-acetylthiophene benzoylhydrazone (ATBH) are characterized in the light of physicochemical and analytical data. Structures of ATAH and ATBH are confirmed by FT-IR, 1H-NMR and Mass spectral data. The hydrazones are screened for their anti-bacterial activities against E Coli, Bacillus cereus, Staphylococcus aureus and Pseudomonas aureoginos. Acetoyl hydrazones are found to show more antibacterial activity than the corresponding benzoyl hydrazones.

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45

Ekram Abdullah Basheer, Kalid Matny Al-jaanaby, and Feras Shauki Al-joboury. "Synthesis a Number of Heterocyclic Compounds Derived From Levofloxacin." Tikrit Journal of Pure Science 20, no. 5 (2023): 84–95. http://dx.doi.org/10.25130/tjps.v20i5.1244.

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In this paper, the preparation a number of heterocyclic compounds five membered rings like oxadiazole, imidazolidine, thiozolidine, tetrazole, azetidine 2-on. Hydrazide (1) was synthesized from the reaction of levofloxacin with hydrazine hydrate. Hydrazone compounds (2-9) were synthesized from the reaction (1) with a number of aldehydes, and 3-acetyl-1,3,4-oxadiazol (10-17) was prepared from the reaction of hydrazones (2-9) with acetic anhydride, 5-oxo-2-aryl imadazoldine derivative (18-25) were prepared from the reaction of hydrazone derivatives (2-9) with glycine, while the reaction of hydrazone with thioglygolic acid gave 4-oxo-2-aryl-thiozolidine (26-33),tetrazole derivative(34-41)prepared from the reaction of hydrazone(2-9) with sodium azide in tetrahyro furan.azetidine-2-on(42-49)with chloro acetyl chloride in DMF and and in the presence of triethyl amine these compounds were characterized on bases of spectral and physical data.

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Kyne, Sara H., and Carl H. Schiesser. "Ab Initio Studies of Carbonyl Radical Additions to Hydrazone Systems." Australian Journal of Chemistry 62, no. 7 (2009): 728. http://dx.doi.org/10.1071/ch09165.

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Ab initio and DFT calculations reveal that intermolecular radical additions of both acyl and oxyacyl radials to hydrazones occur through SOMO → π*hydrazone, πhydrazone → SOMO and LPN → SOMO interactions between the radical and the hydrazone π-system. Both acetyl and methoxycarbonyl radicals show preference for addition to the carbon end of the carbon–nitrogen π-bond. At the highest level of theory used in this study (G2//MP2(full)/6-31G*), energy barriers of 11.2 and 22.6 kJ mol–1 are calculated for acetyl radical addition to the carbon and nitrogen-ends of N-aminomethanimine respectively. The analogous energy barriers for the methoxycarbonyl radical are 4.9 and 25.7 kJ mol–1 at the same level of theory.

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47

Brown, D. Sean, Jason V. Jollimore, Marcus P. Merrin, Keith Vaughan, and Donald L. Hooper. "Formation of methyl 2-arylhydrazono-3-oxobutanoates and 2-arylhydrazono-3-oxobutanenitriles during the coupling reaction of arenediazonium ions with methyl 3-aminocrotonate and 3-aminocrotononitrile." Canadian Journal of Chemistry 73, no. 2 (1995): 169–75. http://dx.doi.org/10.1139/v95-025.

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Reaction of aryldiazonium salts with methyl 3-aminocrotonate (1) affords high yields of the methyl 2-arylhydrazono-3-oxobutanoates (4); analogous diazonium coupling with 3-aminocrotononitrile (2) gives the 2-arylhydrazono-3-oxobutanenitriles (5). The hydrazones are the product of diazonium coupling at the C2-vinylic carbon, concomitant with hydrolysis of the 3-amino substituent to the 3-oxo derivative; there is no evidence for the formation of a triazene (6), which would be the product of N-coupling. All hydrazones (4a–e and 5a–d) have been fully characterized by IR and 1H and 13C NMR spectroscopy; the NMR spectra of the methyl 2-arylhydrazono-3-oxobutanoates (4) suggest the presence of two isomeric intramolecularly H-bonded forms in solution. Selected compounds were further characterized by elemental analysis and mass spectrometry. A mechanism is proposed for the conversion of 1 or 2 into 4 or 5, and these observations are compared with previously reported observations of diazonium coupling reactions with unsaturated systems. Keywords: hydrazone, diazonium, aminocrotonate, aminocrotononitrile, hydrogen bonding.

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Sun, Hong-Xia, Shao-Xuan Gong, Hong-Yang Zhang, et al. "Research Progress on the Reaction of Carbon Dioxide with Hydrazones and Their Derivatives." Molecules 30, no. 9 (2025): 1987. https://doi.org/10.3390/molecules30091987.

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CO2, an abundant and renewable C1 source, presents significant potential for applications in organic synthesis. Hydrazones, recognized for their distinctive properties, exhibit high versatility in synthetic chemistry, facilitating numerous chemical transformations. Given their crucial roles in organic synthesis, the combination of CO2 with hydrazones has garnered increasing research interest. This review provides a comprehensive summary of recent progress in reactions involving CO2 and hydrazones or their derivatives. These include the coupling of amines and N-tosylhydrazones with CO2, the umpolung-mediated carboxylation of hydrazones/N-tosylhydrazones with CO2, the cyclization of hydrazones with CO2, and lactamization reactions incorporating N-tosylhydrazones and CO2. These transformations utilize the diverse reactivity of hydrazones and their derivatives to capture and convert CO2, generating valuable organic compounds with both academic and practical relevance. Additionally, the review examines the mechanisms underlying these reactions, offering critical insights for advancing research in this area.

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Tisovský, Pavol, Miroslav Horváth, Klaudia Csicsai, et al. "Isatin-1,8-Naphthalimide Hydrazones: A Study of Their Sensor and ON/OFF Functionality." Molecules 24, no. 3 (2019): 397. http://dx.doi.org/10.3390/molecules24030397.

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Five novel hydrazones derived from substituted isatins were synthesized as potential anion sensors. Using UV-VIS, FTIR, NMR and fluorescence spectroscopy, these compounds’ tautomeric equilibrium and Z-E photoisomerization were studied in DMF and CHCl3, depending on the hydrazone concentrations, the presence of basic anions and light stimulation. Anion recognition aspects (PF6−, HSO4−, Br−, Cl−, NO3−, F− and CH3COO−) and these receptors’ detection limits were also studied. We also tested the light-stimulated ON-OFF functionality of these compounds in the presence or absence of these anions.

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Teneva, Yoanna, Rumyana Simeonova, Orlin Besarboliev, Hristina Sbirkova-Dimitrova, and Violina T. Angelova. "X-ray Single-Crystal Analysis, Pharmaco-Toxicological Profile and Enoyl-ACP Reductase-Inhibiting Activity of Leading Sulfonyl Hydrazone Derivatives." Crystals 14, no. 6 (2024): 560. http://dx.doi.org/10.3390/cryst14060560.

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Taking into consideration the growing resistance towards currently available antimycobacterials, there is still an unmet need for the development of new chemotherapeutic agents to combat the infectious agents. This study presents X-ray single-crystal analysis to verify the structure of leading sulfonyl hydrazone 3b, which has proven its potent antimycobacterial activity against Mycobacterium tuberculosis H37Rv with an MIC value of 0.0716 μM, respectively, low cytotoxicity, and very high selectivity indexes (SI = 2216), and which has been fully characterized by Nuclear Magnetic Resonance (NMR) and High-Resolution Mass Spectrometry (HRMS) methods. Furthermore, this study assessed the ex vivo antioxidant activity, acute and subacute toxicity, and in vitro inhibition capacity against enoyl-ACP reductase of hydrazones 3a and 3b, as 3a was identified as the second leading compound in our previous research. Compared to isoniazid, compounds 3a and 3b demonstrated lower acute toxicity for intraperitoneal administration, with LD50 values of 866 and 1224.7 mg/kg, respectively. Subacute toxicity tests, involving the repeated administration of a single dose of the test samples per day, revealed no significant deviations in hematological and biochemical parameters or pathomorphological tissues. The compounds exhibited potent antioxidant capabilities, reducing malondialdehyde (MDA) levels and increasing reduced glutathione (GSH). Enzyme inhibition assays of the sulfonyl hydrazones 3a and 3b with IC50 values of 18.2 µM and 10.7 µM, respectively, revealed that enoyl acyl carrier protein reductase (InhA) could be considered as their target enzyme to exhibit their antitubercular activities. In conclusion, the investigated sulfonyl hydrazones display promising drug-like properties and warrant further investigation.

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Journal articles on the topic 'Hydrazones'

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