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Journal articles on the topic '4-naphthoquinone derivatives'

Author: Grafiati

Published: 4 June 2025

Last updated: 1 August 2025

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1

Ma, Qinge, Rongrui Wei, and Zhipei Sang. "Structural Characterization and Hepatoprotective Activity of Naphthoquinone From Cucumis bisexualis." Natural Product Communications 15, no. 1 (2020): 1934578X2090289. http://dx.doi.org/10.1177/1934578x20902898.

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Three new naphthoquinones, namely 5,8-dihydroxy-7′-isopropyl-furan ring-1″-prenyl-naphthoquinone (1), 5,8-dihydroxy-7′-propenyl-furan ring-1″-isopropanol-naphthoquinone (2), and 5,8-dihydroxy-7′-isopropanol-furan ring-1″-(5″-hydroxyphenyl)-naphthoquinone (3), along with 10 known naphthoquinone derivatives (4-13) were isolated from Cucumis bisexualis for the first time. All the compounds were elucidated on the basis of spectroscopic data analysis and chemical evidence. Compounds (1-13) were evaluated for their hepatoprotective activites on human L-O2 cells. Among them, compounds 1, 4, and 8 exh

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2

Rakesh, Kumar Sahu, Kumari Khushbu, Kumari Pooja, et al. "A Review on Properties and Pharmacological Activity of Naphthoquinone and its Derivatives." Chemistry Research Journal 10, no. 2 (2025): 87–94. https://doi.org/10.5281/zenodo.15606076.

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Naphthoquinone forms the central chemical structure of many natural compounds, most notably the K Vitamins. 2-Methylnaphthoquinone is a more effective coagulant than vitamin K. Naphthoquinone derivatives are cytotoxic, they have significant antibacterial, antifungal, antiviral, insecticidal, anti-inflammatory, and antipyretic properties. Quinone derivatives may be toxic to cells by a number of mechanisms including redox cycling, arylation, intercalation, induction of DNA strands breaks, generation of free radicals and alkylation via quinone methide formation. 5-Hydroxy-1, 4-naphthoquinone, jug

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3

Aseeva, Natalia V., Nadezhda V. Danilenko, Evgenii V. Plotnikov, et al. "Synthesis of New 1,4-Naphthoquinone Fluorosulfate Derivatives and the Study of Their Biological and Electrochemical Properties." International Journal of Molecular Sciences 25, no. 22 (2024): 12245. http://dx.doi.org/10.3390/ijms252212245.

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This study presents the synthesis of new fluorosulfate derivatives of 1,4-naphthoquinone by the SuFEx reaction. Anticancer properties of obtained compounds were studied on PC-3 (prostate adenocarcinoma), SKOV-3 (ovarian cancer), MCF-7 (breast cancer), and Jurkat cell lines. All the studied compounds showed higher cytotoxic effects than Cisplatin. The DFT method was applied to determine the electronic structure characteristics of 1,4-naphthoquinone derivatives associated with cytotoxicity. A method of determination of 2,3-dichloro-1,4-naphthoquinone (NQ), 3-chloro-2-((4-hydroxyphenylamino)-1,4-

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4

Ourhzif, El-Mahdi, Caroline Decombat, Isabelle Abrunhosa-Thomas, et al. "Synthesis and Biological Evaluation of New Naphthoquinones Derivatives." Current Organic Synthesis 17, no. 3 (2020): 224–29. http://dx.doi.org/10.2174/1570179417666200212111956.

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: New substituted 1,4-naphthoquinones have been prepared in good overall yields through the naphthol route. The cytotoxicity of these compounds was tested in vitro on MCF-7 breast tumor cells. The most active compound 14 displayed an IC50 of 15μM. Objective: To investigate the cytotoxicity of new naphthoquinones derivatives on MCF-7 cells. Methods: Synthesis of new naphtoquinones derivatives and in vitro evaluation of their cytotoxicity on MCF-7 cells (rezasurin cell-based assay). Results: Starting from Ethyl 4-hydroxy-6,7-dimethoxy-2-naphthoate, four naphthoquinones were prepared and exhibite

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5

Durán, Alexandra G., Nuria Chinchilla, Ana M. Simonet, et al. "Biological Activity of Naphthoquinones Derivatives in the Search of Anticancer Lead Compounds." Toxins 15, no. 5 (2023): 348. http://dx.doi.org/10.3390/toxins15050348.

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Naphthoquinones are a valuable source of secondary metabolites that are well known for their dye properties since ancient times. A wide range of biological activities have been described highlighting their cytotoxic activity, gaining the attention of researchers in recent years. In addition, it is also worth mentioning that many anticancer drugs possess a naphthoquinone backbone in their structure. Considering this background, the work described herein reports the evaluation of the cytotoxicity of different acyl and alkyl derivatives from juglone and lawsone that showed the best activity resul

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6

Kacmaz, Aysecik, Nahide Gulsah Deniz, Serdar Goksin Aydinli, et al. "Synthesis and antiproliferative evaluation of some 1,4-naphthoquinone derivatives against human cervical cancer cells." Open Chemistry 17, no. 1 (2019): 337–45. http://dx.doi.org/10.1515/chem-2019-0030.

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AbstractIn the course of biological properties of quinone derivatives, the N(H)-, S- and S,S-substituted-1,4-naphthoquinones were synthesized by reactions of 2,3-dichloro-1,4-naphthoquinone with different amines (2-morpholinoaniline, tert-butyl 4-aminobenzoate, 4-tert-butylbenzylamine, N-(3-aminopropyl)-2-pipecoline, 2-amino-5,6-dimethylbenzothiazole, N,N'-diphenyl-p-phenylenediamine) and thiolat (sodium 2-methyl-2-propanethiolate). All new products were characterized by MS-ESI, UV-Vis, FT-IR, 1H NMR, 13C NMR. The antiproliferative activities of these compounds on human cervical cancer (HeLa)

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7

Kurka, M. S., I. R. Buchkevych, A. S. Krvavych, et al. "The study of the interaction of 1,2- and 1,4-naphthoquinones with aminophosphonic esters." Voprosy Khimii i Khimicheskoi Tekhnologii, no. 2 (April 2024): 39–46. http://dx.doi.org/10.32434/0321-4095-2024-153-2-39-46.

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A number of new biologically active phosphorus-containing quinones were prepared by the reaction of 2,3-dichloro-1,4-naphthoquinone and sodium 1,2-naphthoquinone-4-sulfonate with phosphonate nucleophilic reagents, aminophosphonic acid esters. The structures of the synthesized compoumds were confirmed by ESI-MS, 1H NMR, IR-spectroscopies and elemental analysis. It was shown that aminophosphonic esters form products of nucleophilic substitution of a chlorine atom of 1,4-naphthoquinone or a sulfonyl group of 1,2-naphthoquinone on an aminophosphonic fragment. The products of the interaction of sod

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8

Ratti, Pichayaporn, Jutharat Manuschai, Jiraporn Kara, Luelak Lomlim, and Supawadee Naorungroj. "In Vitro Antimicrobial, Antiglycolytic, and Antibiofilm Activities of Synthetic 1,4-Naphthoquinone Derivatives against Cariogenic Bacteria." Sains Malaysiana 52, no. 1 (2023): 199–210. http://dx.doi.org/10.17576/jsm-2023-5201-16.

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This study investigated the potential anticaries properties of synthetic 1,4-naphthoquinone derivatives. Synthetic 1,4-naphthoquinone derivatives (2-4) were designed and synthesized by employing lawsone methyl ether (LME, 1), a plant-derived 1,4-naphthoquinone, as a lead compound. The synthetic compounds were characterized by infrared spectroscopy, 1H-nuclear magnetic spectroscopy, 13C- nuclear magnetic spectroscopy, and high-resolution mass spectrometry. Minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), and growth curves were determined to assess their antibact

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9

Kim, Kyeongha, Hun Young Kim, and Kyungsoo Oh. "ortho-Naphthoquinone-catalyzed aerobic oxidation of amines to fused pyrimidin-4(3H)-ones: a convergent synthetic route to bouchardatine and sildenafil." RSC Advances 10, no. 52 (2020): 31101–5. http://dx.doi.org/10.1039/d0ra06820a.

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10

Nataliia, Polish, Voitsakhivska Olha, Marintsova Nataliia, Zhurakhivska Lesya, Novikov Volodymyr, and Bohza Serhii. "Primary screening of the biological activity of heterocyclic aminoderivatives of 2,3-dichloro-1,4-naphtoquinone." ScienceRise: Pharmaceutical Science, no. 6(22) (December 30, 2019): 37–42. https://doi.org/10.15587/2519-4852.2019.188127.

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<strong>The aim.</strong> Check the antimicrobial and fungicidal activity of 2,3-dichloro-1,4-naphthoquinone aminopyrazole derivatives and predict their severity of toxicity to rats. <strong>Materials and methods of the research.</strong> The antimicrobial activity of heterocyclic amino derivatives of naphthoquinone 3a-d was studied by diffusion of the substance into agar on solid nutrient medium and by serial dilution. Acute rodent toxicity was determined by the QSAR simulation method implemented in GUSAR software. <strong>Results.</strong> In the work, the antimicrobial and fu

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11

Lukeman, Matthew, Duane Veale, Peter Wan, V. Ranjit N. Munasinghe, and John ET Corrie. "Photogeneration of 1,5-naphthoquinone methides via excited-state (formal) intramolecular proton transfer (ESIPT) and photodehydration of 1-naphthol derivatives in aqueous solution." Canadian Journal of Chemistry 82, no. 2 (2004): 240–53. http://dx.doi.org/10.1139/v03-184.

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The photochemistry of naphthols 1, 2, 4, 5 and 9, and phenol 10 has been studied in aqueous solution with the primary aim of exploring the viability of such compounds for naphthoquinone and quinone methide photogeneration, along the lines already demonstrated by our group for phenol derivatives. 1-Naphthol (1) is known to be substantially more acidic than 2-naphthol (2) in the singlet excited state (pKa* = 0.4 and 2.8, respectively) and it was expected that this difference in excited-state acidity might be manifested in higher reactivity of 1-naphthol derivatives for photochemical reactions re

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12

Bailey, David, Jeffrey N. Murphy, and Vance E. Williams. "From enolates to anthraquinones." Canadian Journal of Chemistry 84, no. 4 (2006): 659–66. http://dx.doi.org/10.1139/v06-054.

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A series of highly reactive cyclopentadienones were prepared in situ from the corresponding hydroxycyclopent-2-enones and trapped with a variety of quinones. Reaction of 1,4-naphthoquinone with 4-hydroxy-3,4-diphenyl-cyclopent-2-enone afforded 2,3-diphenylanthraquinone, whereas reaction of benzoquinone with this same cyclopentadienone precursor yielded a mixture of 6,7-diphenyl-1,4-naphthoquinone and 2,3,6,7-tetraphenyl anthraquinone. A number of other 2,3-diarylanthraquinones were likewise prepared in moderate yields from the reaction of 1,4-naphthoquinone with the appropriate 4-hydroxy-3,4-d

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13

Feng, Zikai, Mohammed Sedeeq, Abraham Daniel, et al. "Comparative In Vitro Toxicology of Novel Cytoprotective Short-Chain Naphthoquinones." Pharmaceuticals 13, no. 8 (2020): 184. http://dx.doi.org/10.3390/ph13080184.

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Short-chain quinones (SCQs) have been identified as potential drug candidates against mitochondrial dysfunction, which largely depends on the reversible redox characteristics of the active quinone core. We recently identified 11 naphthoquinone derivatives, 1–11, from a library of SCQs that demonstrated enhanced cytoprotection and improved metabolic stability compared to the clinically used benzoquinone idebenone. Since the toxicity properties of our promising SCQs were unknown, this study developed multiplex methods and generated detailed toxicity profiles from 11 endpoint measurements using t

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14

Bisoli, Eder, Talita Vilalva Freire, Nídia Cristiane Yoshida, et al. "Cytotoxic Phenanthrene, Dihydrophenanthrene, and Dihydrostilbene Derivatives and Other Aromatic Compounds from Combretum laxum." Molecules 25, no. 14 (2020): 3154. http://dx.doi.org/10.3390/molecules25143154.

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The chemical investigation of the roots and stems of Combretum laxum yielded a new dihydrostilbene derivative, 4′-hydroxy-3,3′,4-trimethoxy-5-(3,4,5-trimethoxyphenoxy)-bibenzyl (1), two phenanthrenes (2–3), and three dihydrophenanthrenes (4–6), along with one lignan, three triterpenoids, one aurone, one flavone, one naphthoquinone, and two benzoic acid derivatives. Their structures were determined by 1D and 2D nuclear magnetic resonance (NMR) spectroscopic techniques and/or mass spectrometry data. The occurrence of dihydrostilbenoid, phenanthrene and dihydrophenanthrene derivatives is unpreced

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15

Coulidiati, Tangbadioa H., Bruna B. Dantas, Glaucia V. Faheina-Martins, Enéas Ricardo de Morais Gomes, Juan C. R. Gonçalves, and Demetrius A. Machado de Araújo. "Proapoptotic Effects of triazol-1,4-Naphthoquinones Involve Intracellular ROS Production and MAPK/ERK Pathway in Human Leukemia Cells." Anti-Cancer Agents in Medicinal Chemistry 20, no. 17 (2020): 2089–98. http://dx.doi.org/10.2174/1871520620666200721124221.

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Background : The natural products constitute an important source of antitumor and cytotoxic agents. Naphthoquinones are effectively quinones present in different plants, with demonstrated anticancer activities. A recent study conducted by our group demonstrated the antileukemic potential of two novel triazol-1,4- naphthoquinones derivatives, PTN (2-(4-Phenyl-1H-1,2,3-triazol-1-yl)-1,4-naphthoquinone) and MPTN (2-[4- (4-Methoxyphenyl)-1H-1,2,3-triazol-1-yl]-1,4-naphthoquinone). Although, the mechanisms underlying the proapoptotic effects of PTN and MPTN have not been fully elucidated so far. Ob

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16

Hardesh, K. Maurya. "SYNTHETIC AND BIOLOGICAL UTILITY OF 2,3-DICHLORO-1,4- NAPHTHOQUINONE: A REVIEW." International Journal of Research - Granthaalayah 7, no. 10 (2019): 293–347. https://doi.org/10.5281/zenodo.3525162.

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2,3-Dichloro-1,4-naphthoquinones (dichlone) have attracted considerable attention for the construction of biologically active tricyclic and tetracyclic 1,4-quinones and other derivatives. A diversified reaction of 2,3-dichloro-1,4-naphthoquinones such as cycloaddition, condensation, photo induced and nucleophilic substitution reactions with suitable nucleophiles viz. carbon, nitrogen, oxygen, sulfur, selenium etc have been explored. Various synthesized compounds have also explored for their biological activity such as antifungal, antibacterial, anticancer, antiplatlet, anti-inflamentry, anti-a

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17

Shvartsberg, M. S., A. A. Moroz, N. V. Ivashkina, and S. B. Cherepanov. "Synthesis of 5-ethynyl-l,4-naphthoquinone and its derivatives." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 35, no. 11 (1986): 2273–78. http://dx.doi.org/10.1007/bf00953338.

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18

Liu, Hongju, Chong Yan, Changqun Li, Tingting You, and Zhigang She. "Naphthoquinone Derivatives with Anti-Inflammatory Activity from Mangrove-Derived Endophytic Fungus Talaromyces sp. SK-S009." Molecules 25, no. 3 (2020): 576. http://dx.doi.org/10.3390/molecules25030576.

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Twelve 1, 4-naphthoquinone derivatives, including two new (1 and 2) and 10 known (3–12), were obtained from endophytic fungus Talaromyces sp. SK-S009 isolated from the fruit of Kandelia obovata. All structures were identified through extensive analysis of the nuclear magnetic resonance (NMR), mass spectrometry (MS) and circular dichroism (CD), as well as by comparison with literature data. These compounds significantly inhibited the lipopolysaccharide (LPS)-induced nitric oxide (NO) production in the murine macrophage cell line (RAW 264.7 cells). The half maximal inhibitory concentration (IC50

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19

WURM, G., and H. J. DUCHSTEIN. "ChemInform Abstract: 1,4-Naphthoquinones. Part 24. On the Dehalogenation of 2-/3-Halogen-1, 4-naphthoquinone Derivatives." ChemInform 26, no. 28 (2010): no. http://dx.doi.org/10.1002/chin.199528064.

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20

Hassan, Alaa, Nasr Mohamed, Kamal El-Shaieb, Hendawy Tawfeek, Stefan Bräse, and Martin Nieger. "Eschenmoser Coupling Reaction and Reactivity of Hydrazinecarbothioamides in the Synthesis of Benzindazole and Naphthothiazole Derivatives." Synthesis 49, no. 16 (2017): 3720–25. http://dx.doi.org/10.1055/s-0036-1588179.

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N-Unsubstituted and N-substituted 2-phenylhydrazinecarbothioamides react with 2,3-dichloro-1,4-naphthoquinone to give a series of unprecedented 3-amino- and 3-(alkylamino)-1-phenyl-1H-benzo[f]indazole-4,9-diones in good yields. On the other hand, the reaction of N-substituted 2-tosylhydrazinecarbothioamides with 2,3-dichloro-1,4-naphthoquinone afforded (Z)-N-[3-(tosylamino)-4,9-dioxo-4,9-dihydronaphtho[2,3-d]thiazol-2(3H)-ylidene]-substituted aminium chlorides and (Z)-N-[(2-substituted imino)-4,9-dioxo-4,9-dihydronaphtho[2,3-d]thiazol-3(2H)-yl]-4-toluenesulfonamide hydrates.

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21

El-Shaieb, Kamal M., Mohamed A. Ameen, Fathy F. Abdel-latif, and Asmaa H. Mohamed. "Facile Synthesis of Thiazole, Thiazine and Isoindole Derivatives via EDA Approach and Conventional Methods." Zeitschrift für Naturforschung B 68, no. 8 (2013): 905–12. http://dx.doi.org/10.5560/znb.2013-3117.

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The reactivity of N-amidinothiourea (1) as an electron donor towards several electron-accepting functional groups via electron-donor-acceptor (EDA) interaction has been studied. Thus on treatment of 1 with either 1,1,2,2-tetracyanoethylene (TCNE, 2), 2,3-dicyano-1,4-naphthoquinone (DCNQ, 4), 2,3,5,6-tetrabromo-1,4-benzoquinone (BHL-p, 6), 2,3-dichloro-1,4-naphthoquinone (DCHNQ, 8), 2,3,5,6-tetrachloro-1,4-benzoquinone (CHL-p, 13), 2,3-dicyano-5,6-dichloro-1,4- benzoquinone (DDQ, 15), 2-dicyanomethyleneindan-1,3-dione (CNIND, 17), 2-(2-oxoindolin-3- ylidene)malononitrile (19), and/or dimethyl a

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22

KALLMAYER, H. J., and M. BINGER. "ChemInform Abstract: 2-Dichloromethylnaphthimidazole Quinones. Part 4. Heterocyclic 1,4- Naphthoquinone Derivatives." ChemInform 22, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.199135149.

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23

Gornostaev, Leonid M., Daria S. Rudenko, Sergey D. Kirik, and Vyacheslav I. Krasnov. "INTERACTION OF (4E)-3-ALKYL(BENZYL)AMINO-4-(HYDROXYIMINO)NAPHTHALENE-1(4H)-ONES WITH 2,2-DIHYDROXY-1,3-INDANEDIONE." ChemChemTech 67, no. 5 (2024): 24–35. http://dx.doi.org/10.6060/ivkkt.20246705.7015.

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Many natural and synthetic quinone, including naphthoquinone derivatives, have some valuable properties. They are known as dyes, antibiotics, vitamins, and antioxidants. Some naphthoquinone derivatives act as cytostatic and antitumor reagents. However, the reduction of the quinoid fragment to the semiquinone radical and, as a consequence, the formation of toxic anion radicals, makes these substances cardiotoxic. The replacement of one or both carbonyl groups with the imino fragment can be one of the ways to solve this problem because iminoquinones have a weak redox cycle. This paper presents t

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24

Abdassalam, Aesha F. SH, Nahide Gulsah Deniz, Cigdem Sayil, Mustafa Ozyurek, Emin Ahmet Yesil, and Huseyin Salihoglu. "Synthesis of New Regioisomers of 5-Nitro-1,4-Naphthoquinone, Evaluation of Antioxidant and Catalase Inhibition Activities." Acta Chimica Slovenica 69, no. 1 (2022): 187–99. https://doi.org/10.17344/acsi.2021.7123.

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The studies on nitronaphthoquinone derivatives are rare in the literature, and the nitro group associated with the aromatic ring in the quinone system is known to increase the biological activity of naphthoquinone due to its electron-withdrawing properties. In the course of quinone derivatives, the new N(H)-substituted-5-nitro-1,4-naphthoquinones (NQ) as regioisomers were synthesized by reactions of 2,3-dichloro-5-nitro-1,4-naphthoquinone with some heterocyclic ring substituted nucleophiles such as anilines, piperazines, or morpholines, according to a Michael 1,4-addition mechanism. Five NQ re

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25

FERNANDES, M. C., E. N. DA SILVA, A. V. PINTO, S. L. DE CASTRO, and R. F. S. MENNA-BARRETO. "A novel triazolic naphthofuranquinone induces autophagy in reservosomes and impairment of mitosis in Trypanosoma cruzi." Parasitology 139, no. 1 (2011): 26–36. http://dx.doi.org/10.1017/s0031182011001612.

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SUMMARYChagas' disease, caused by the protozoan Trypanosoma cruzi, represents a serious health problem in Latin America, and the available chemotherapy, which is based on 2 nitro-derivatives, is not satisfactory. In folk medicine, natural products including naphthoquinones have been employed for the treatment of different parasitic diseases. In the pursuit of alternative drugs for Chagas' disease, we investigated the mechanism of action of the triazolic naphthoquinone (TN; 2,2-dimethyl-3-(4-phenyl-1H-1,2,3-triazol-1-yl)-2,3-dihydronaphtho[1,2-b]furan-4,5-dione), which is the most active compou

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26

Salari, Maryam, Mohammad H. Mosslemin, and Alireza Hassanabadi. "Synthesis of a series of novel 2,3-dihydrofuranonaphthoquinone derivatives." Journal of Chemical Research 41, no. 8 (2017): 448–51. http://dx.doi.org/10.3184/174751917x14999542807785.

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A green and highly efficient synthesis of 12 novel trans-2-(4-chlorobenzoyl)-3-aryl-2,3-dihydronaphtho[2,3- b]furan-4,9-diones has been achieved via a three-component, one-pot condensation of 2-[2-(4-chlorophenyl)-2-oxoethyl)]isoquinolinium bromide with 2-hydroxy-1,4-naphthoquinone and an aromatic aldehyde in the presence of catalytic amounts of choline hydroxide in water under reflux conditions. The advantages of this method are a short reaction time, high yields and the avoidance of any hazardous organic solvent. Therefore, this procedure can be classified as green chemistry.

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Aesha F SH Abdassalam, Aesha F. SH Abdassalam, Semih Kurban Semih Kurban, and Nahide Gulsah Deniz and Cigdem Sayil Nahide Gulsah Deniz and Cigdem Sayil. "Synthesis and Characterization of New Naphtho- and Tetracyclic Diazaquinone Derivatives." Journal of the chemical society of pakistan 41, no. 5 (2019): 834. http://dx.doi.org/10.52568/000805/jcsp/41.05.2019.

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In this study, new 1,4-naphtho- and 5-nitro-1,4-naphtho derivatives containing N- and N,N-substituted groups which has not been reported yet, have been synthesized from 2,3-dichloronaphthalene-1,4-diones (1,9). Compounds of 2-choloro-3-((2,4,6-triflorophenyl)amino)naphthalene-1,4-dione (3) and 2-chloro-3-((4-florophenyl)amino)naphtalene-1,4-dione (7) were obtained by reactions of 2,3-dichloronaphthalene-1,4-dione 1 with 4-fluoroaniline (6) and 2,4,6-trifloroaniline (2), respectively involving a Michael addition. We reported the cyclization reactions of compounds 1 to benzo[g]pirido[3,2-b]quino

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Schneider, Ingrid, and Erich F. Elstner. "Antioxidative Properties of Phenazone Derivatives: Differentiation between Phenylbutazon and Mofebutazon." Zeitschrift für Naturforschung C 48, no. 7-8 (1993): 542–44. http://dx.doi.org/10.1515/znc-1993-7-802.

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Abstract Both phenylbutazon and mofebutazon inhibit oxidative fragmentation of the methionine derivative, 2-keto-4-methylthio-butyric acid (KMB) by xanthine oxidase - or diaphorase me diated OH radical production. Differentiation of the two non-steroidal antiinflammatory drugs is possible by means of determining oxygen reduction by xanthine oxidase or diaphorase in the presence of the naphthoquinone, juglone, where only mofebutazon shows an inhibitory effect.

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Thanh, Nguyen Ha, Hoang Thi Phuong, Le Nhat Thuy Giang, et al. "4-(Dimethylamino)pyridine as an Efficient Catalyst for One-Pot Synthesis of 1,4-Pyranonaphthoquinone Derivatives viaMicrowave-Assisted Sequential Three Component Reaction in Green Solvent." Natural Product Communications 16, no. 11 (2021): 1934578X2110539. http://dx.doi.org/10.1177/1934578x211053951.

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Novel 1,4-pyranonaphthoquinone derivatives were successfully synthesized via the microwave-assisted three-component reaction of 1,4-naphthoquinone, malononitrile, and various arylaldehydes in ethanol in the presence of 4-(dimethylamino)pyridine (DMAP) as a catalyst, and subsequently evaluated in terms of their antimicrobial and antifungal activities. This synthetic procedure has the notable advantages of environmental friendliness, short reaction time, good yield, and convenient operation.

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30

KALLMEYER, H. J., and M. BINGER. "ChemInform Abstract: Heterocyclic 1,4-Naphthoquinone Derivatives. Part 3. 4-Phenylbenzo(g) chinoxalinetrione." ChemInform 22, no. 49 (2010): no. http://dx.doi.org/10.1002/chin.199149200.

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31

Cabral, Rafaela G., Gonçalo Viegas, Rita Pacheco, Ana Catarina Sousa, and Maria Paula Robalo. "Sustainable Synthesis, Antiproliferative and Acetylcholinesterase Inhibition of 1,4- and 1,2-Naphthoquinone Derivatives." Molecules 28, no. 3 (2023): 1232. http://dx.doi.org/10.3390/molecules28031232.

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This work describes the design, sustainable synthesis, evaluation of electrochemical and biological properties against HepG2 cell lines, and AChE enzymes of different substituted derivatives of 1,4- and 1,2-naphthoquinones (NQ). A microwave-assisted protocol was optimized with success for the synthesis of the 2-substituted-1,4-NQ series and extended to the 4-substituted-1,2-NQ family, providing an alternative and more sustainable approach to the synthesis of naphthoquinones. The electrochemical properties were studied by cyclic voltammetry, and the redox potentials related to the molecular str

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Palacios, Javier, José Miguel Fonseca, Fernando Ayavire, et al. "Ascorbate Attenuates Oxidative Stress and Increased Blood Pressure Induced by 2-(4-Hydroxyphenyl) Amino-1,4-naphthoquinone in Rats." Oxidative Medicine and Cellular Longevity 2018 (July 26, 2018): 1–11. http://dx.doi.org/10.1155/2018/8989676.

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Quinone derivatives like 2-(4-hydroxyphenyl) amino-1,4-naphthoquinone (Q7) are used as antitumor agents usually associated with adverse effects on the cardiovascular system. The objective of this study was to evaluate the cardioprotective effect of ascorbate on Q7-induced cardiovascular response in Wistar rats. In this study, blood pressure, vascular reactivity, and intracellular calcium fluxes were evaluated in cardiomyocytes and the rat aorta. We also measured oxidative stress through lipid peroxidation (TBARS), superoxide dismutase- (SOD-) like activity, and H2O2 generation. Oral treatment

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Gokhale, Nikhil, Subhash Padhye, Chris Newton, and Robin Pritchard. "Hydroxynaphthoquinone Metal Complexes as Antitumor Agents X: Synthesis, Structure, Spectroscopy and In Vitro Antitumor Activity of 3-Methyl-Phenylazo Lawsone Derivatives and Their Metal Complexes Against Human Breast Cancer Cell Line MCF-7." Metal-Based Drugs 7, no. 3 (2000): 121–28. http://dx.doi.org/10.1155/mbd.2000.121.

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The C-3 substituted phenylazo derivatives of lawsone (2-hydroxy-l,4 p-naphthoquinone, III) were synthesized and characterized. The X-ray crystal structure was determined for the ligand 3-(3′-methyl phenylazo) lawsone. The copper complexes of these derivatives were found to possess 1:2 metal stoichiometry and square planar geometries with intermolecular stackings, resulting in antiferromagnetic exchange interactions. The in vitro activity of all the synthesized compounds was examined against human breast cancer cell-line, MCF-7, which revealed enhanced activities for the metal complexes, the hi

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Palacios, Javier, Fredi Cifuentes, Jaime A. Valderrama, et al. "Modulatory Effect of 2-(4-Hydroxyphenyl)amino-1,4-naphthoquinone on Endothelial Vasodilation in Rat Aorta." Oxidative Medicine and Cellular Longevity 2016 (2016): 1–12. http://dx.doi.org/10.1155/2016/3939540.

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The vascular endothelium plays an essential role in the control of the blood flow. Pharmacological agents like quinone (menadione) at various doses modulate this process in a variety of ways. In this study,Q7, a 2-phenylamino-1,4-naphthoquinone derivative, significantly increased oxidative stress and induced vascular dysfunction at concentrations that were not cytotoxic to endothelial or vascular smooth muscle cells.Q7reduced nitric oxide (NO) levels and endothelial vasodilation to acetylcholine in rat aorta. It also blunted the calcium release from intracellular stores by increasing the pheny

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Shishkina, R. P., V. N. Berezhnaya, and E. P. Fokin. "Synthesis and photochemical conversions of piperazine derivatives of 2-chloro-l,4-naphthoquinone." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 34, no. 10 (1985): 2160–64. http://dx.doi.org/10.1007/bf00963254.

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Bansal, Mukesh, Bharat Goel, Shubhanjali Shukla, and Radhey Shyam Srivastava. "Synthesis, characterization & anticonvulsant activity of amide derivatives of 4-amino-1,2-naphthoquinone." Medicinal Chemistry Research 22, no. 11 (2013): 5349–55. http://dx.doi.org/10.1007/s00044-013-0531-6.

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Ocampo, Yanet, Jenny Castro, Jhoan Piermattey, Ricardo Gaitan, and Luis Franco. "Synthetic naphthoquinone derivatives suppressed nitric oxide and prostaglandin E2 production." Trends in Immunotherapy 7, no. 2 (2023): 2417. http://dx.doi.org/10.24294/ti.v7.i2.2417.

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Objectives: To synthesize and evaluate the anti-inflammatory potential of fifteen naphthoquinones (NQs), determining their ability to inhibitory nitric oxide (NO•) and prostaglandin E2 (PGE2) production. Methods: NQs were screened for their inhibitory effect on NO• and PGE production using LPS-activated RAW 264.7 macrophages. Results: Three linear furanonaphthoquinones (4-6) were identified as potent inhibitors of NO• and PGE2 production, with IC50 values ranging from 0.45 to 2.86 μM (NO•) and 0.38 to 1.65 (PGE2), highlighting the potent activity showed by compound 5 with IC50 values lower tha

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Khanna, Garima, Komal Aggarwal, and Jitender M. Khurana. "An efficient and confluent approach for the synthesis of novel 3,4-dihydro-2H-naphtho[2,3-e][1,3]oxazine-5,10-dione derivatives by a three component reaction in ionic liquid." RSC Advances 5, no. 58 (2015): 46448–54. http://dx.doi.org/10.1039/c5ra06169e.

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Sayil, Cigdem, Nahide Deniz, Erhan Oner, Damla Koc, Mustafa Ozyurek, and Kubilay Guclu. "A method for dyeing polyester fibres with quinone derivatives and evaluation of their antioxidant activity." Chemical Industry and Chemical Engineering Quarterly 24, no. 1 (2018): 85–92. http://dx.doi.org/10.2298/ciceq161026022s.

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In this study, a series of bis(thio)substituted-1,4-naphthoquinone compounds (4a-j) were synthesized via Michael addition reaction and their structures were determined by infrared spectrometry, 1H and 13C nuclear magnetic resonance spectroscopy, mass spectrometry and elemental analysis. The synthesized substances were applied to polyester fibers and the dyeing properties were investigated. The rubbing fastness, wash fastness and optical properties of synthesized compounds were also studied. The color change and staining test results were found to be ?4? to ?4-5? for the most of the dyed sample

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Kavaliauskas, Povilas, Birutė Grybaitė, Rita Vaickelionienė, et al. "Synthesis and Development of N-2,5-Dimethylphenylthioureido Acid Derivatives as Scaffolds for New Antimicrobial Candidates Targeting Multidrug-Resistant Gram-Positive Pathogens." Antibiotics 12, no. 2 (2023): 220. http://dx.doi.org/10.3390/antibiotics12020220.

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The growing antimicrobial resistance to last-line antimicrobials among Gram-positive pathogens remains a major healthcare emergency worldwide. Therefore, the search for new small molecules targeting multidrug-resistant pathogens remains of great importance. In this paper, we report the synthesis and in vitro antimicrobial activity characterisation of novel thiazole derivatives using representative Gram-negative and Gram-positive strains, including tedizolid/linezolid-resistant S. aureus, as well as emerging fungal pathogens. The 4-substituted thiazoles 3h, and 3j with naphthoquinone-fused thia

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Напалкова, Светлана Михайловна, and Ольга Владимировна Буюклинская. "EFFECT OF 1,4-NAPHTHOQUINONE ALKYLATED AMINO ACIDS DERIVATIVES ON CARDIOHEMODYNAMICS ON ISCHEMIC MYOCARDIUM MODEL." ВЕСТНИК ОБРАЗОВАНИЯ И РАЗВИТИЯ НАУКИ РОССИЙСКОЙ АКАДЕМИИ ЕСТЕСТВЕННЫХ НАУК, no. 4 (December 15, 2021): 66–71. http://dx.doi.org/10.26163/raen.2021.48.21.010.

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Изучалось влияние производных трех аминокислот (глицин, глютаминовая и аспарагиновая кислоты), алкилированных 1,4-нафтохиноном, на кардиогемодинамику на модели ишемизированного миокарда. Установлено, что все исследованные соединения (лабораторные шифры НХА, НХГ, НХГА) на модели ишемии миокарда, вызванной окклюзией коронарной артерии, предупреждали снижение сократимости сердечной мышцы. Производное глицина (НХГ) в большей степени предупреждало снижение уровня среднего артериального давления, тогда как наименее заметное влияние на этот показатель оказывало соединение с лабораторным шифром НХГК (

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Kose, Mahmut, Çiğdem Yıldırım Şekerci, Kazushi Suzuki, and Yasushi Yokoyama. "Synthesis of photochromic 2,3-bis(5-methyl-2-phenyl-4-thiazolyl)-1,4-naphthoquinone derivatives." Journal of Photochemistry and Photobiology A: Chemistry 219, no. 1 (2011): 58–61. http://dx.doi.org/10.1016/j.jphotochem.2011.01.016.

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Christodoulou, Michael S., Sabrina Giofrè, Egle M. Beccalli, Francesca Foschi, and Gianluigi Broggini. "Divergent Conversion of 4-Naphthoquinone-substituted 4H-Isoxazolones to Different Benzo-fused Indole Derivatives." Organic Letters 22, no. 7 (2020): 2735–39. http://dx.doi.org/10.1021/acs.orglett.0c00709.

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Thuy Giang, Le Nhat, Dang Thi Tuyet Anh, Hoang Thi Phuong, et al. "DMAP-catalyzed Efficient and Convenient Approach for the Synthesis of 3,3′-(Arylmethylene)bis(2-Hydroxynaphthalene-1,4-Dione) Derivatives." Natural Product Communications 16, no. 9 (2021): 1934578X2110458. http://dx.doi.org/10.1177/1934578x211045808.

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For the first time the 4-dimethylaminopyridine (DMAP) catalyzed straightforward and efficient procedure has been developed for the synthesis of 3,3′-(arylmethylene) bis(2-hydroxynaphthalene-1,4-dione) derivatives starting from lawsone (2-hydroxy-1,4-naphthoquinone) and a variety of (hetero)aromatic aldehydes in ethanol under microwave irradiation. Three of nine synthesized compounds are new. This method provides notable advantages over existing procedures including use of non-traditional basic catalyst and environmentally benign solvent, mild reaction conditions, excellent yields, short reacti

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Mahmoudi, Abdelghani, and Silvia Francia. "Comparative analysis and application of novel spectrophotometric approaches and bioassay for fast macrolide quantification in table." Chemistry Journal of Moldova 20, no. 1 (2025): 7–16. https://doi.org/10.19261/cjm.2025.1312.

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Novel spectrophotometric methods and bioassays have been developed and validated for clarithromycin quantitation in tablets. Spectrophotometric techniques were based on charge transfer complexation through naphthoquinone derivatives. Reactions were carried out in alkaline medium using 1,2-naphthoquinone-4-sulphonate and phylloquinone, which showed an absorption maximum at 452 and 455 nm, respectively. While bioassay was conducted dependent on the inhibitory effect upon the strain of Bacillus subtilis ATCC 9372, by applying cylinder-plate. Linear calibration curves with correlation coefficients

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Polish, N. V., N. G. Marintsova, A. I. Karkhut, O. S. Yaremkevysh, and O. V. Karpenko. "Antioxidant activity of heterocyclic amino containing derivatives of naphthoquinone and their compositions with surface-active rhamnolipids." Chemistry, Technology and Application of Substances 4, no. 1 (2021): 109–15. http://dx.doi.org/10.23939/ctas2021.01.109.

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Composite preparations based on heterocyclic amine-containing naphthoquinone derivatives and surfactant rhamnolipids were obtained. The intensity of the processes of lipid peroxidation (LPO), oxidative modification of proteins (OMB) and radical-absorbing activity against 1,1-diphenyl-2-picrylhydrazyl (DFPG) was studied. Compounds exhibiting high antioxidant activity against LPO and OMB processes were identified, namely: 2-[(6-(4-fluorophenyl-5-oxo-2,5-dihydro-1,2,4-triazin-3-yl) phenyl)amino]naphthalene-1,4-dione 1d and its composite preparation with rhamnolipid 1d + RL. It was found that all

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Sivakumar, Dhanavel, Jayaraman Thanusu, Vijayakumar Kanagarajan, Samuthira Nagarajan, Haridoss Manikandan, and Mannathusamy Gopalakrishnan. "One-pot Synthesis of 2-Hydroxy-1,4-Naphthoquinone (Lawsone)." Current Organic Synthesis 16, no. 3 (2019): 431–34. http://dx.doi.org/10.2174/1570179416666190111155328.

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Aims and Scope: The 2-hydroxy-1,4-naphthoquinone (lawsone) and 2,5-dihydroxy-1, 4-naphthoquninone (5-hydroxylawsone) are synthesized by one step process. The process involves an inexpensive catalyst urea hydrogen peroxide and a base (t-BuOK) in alcohol for the transformation of 1-naphthol or 2,5-dihydroxynaphthalene to lawsone or its derivatives in the presences of oxygen. The process is further directed to produce lawsone or its derivatives, with no extraneous heating to make it energetically efficient. The synthesized compounds are analyzed by FT-IR, 1H and 13C NMR spectral studies. Material

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Kim, Kyungmin, Daseul Kim, Hyunjin Lee, Tae Hoon Lee, Ki-Young Kim, and Hakwon Kim. "New Pyrimidinone-Fused 1,4-Naphthoquinone Derivatives Inhibit the Growth of Drug Resistant Oral Bacteria." Biomedicines 8, no. 6 (2020): 160. http://dx.doi.org/10.3390/biomedicines8060160.

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Background: Dental caries is considered to be a preventable disease, and various antimicrobial agents have been developed for the prevention of dental disease. However, many bacteria show resistance to existing agents. Methods/Principal Findings: In this study, four known 1,4-naphthoquinones and newly synthesized 10 pyrimidinone-fused 1,4-naphthoquinones, i.e. KHQ 701, 702, 711, 712, 713, 714, 715, 716, 717 and 718, were evaluated for antimicrobial activity against Enterococcus faecalis, Enterococcus faecium, Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus mutans, Streptococcu

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BOUAMMALI, B., F. PAUTET, and H. FILLION. "ChemInform Abstract: Regiochemistry in the Cycloaddition of Disilylated 2-Azadienes with 1, 4-Naphthoquinone Derivatives." ChemInform 23, no. 32 (2010): no. http://dx.doi.org/10.1002/chin.199232068.

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Uysal, Sirin, Zeynep Soyer, Merve Saylam, Ayse H. Tarikogullari, Sinem Yilmaz, and Petek Ballar Kirmizibayrak. "Design, synthesis and biological evaluation of novel naphthoquinone-4-aminobenzensulfonamide/carboxamide derivatives as proteasome inhibitors." European Journal of Medicinal Chemistry 209 (January 2021): 112890. http://dx.doi.org/10.1016/j.ejmech.2020.112890.

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