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Design and Evaluation of Antimicrobial Activity of New Pyrazole, 1,2,4-Triazole, and 1,3,4-Thiadiazol Derivatives Bearing 1,4-Dihydroquinoxaline Moiety

Abstract

An effective method for synthesizing a series of fifteen new compounds ethyl 3-(2-(3-amino-1,4-dihydroquinoxaline-2-carbonyl)hydrazono )butanoate (II), 3-amino-N'-benzylidene-1,4-dihydroquinoxaline-2-carbohydrazide dérivatives (IVVI), phenyl)-4-oxothiazolidin-3-yl)-1,4-dihydroquinoxaline-2-carboxamide derivatives (VIIIX), 3-(3-amino-1,4-dihydroquinoxalin-2-yl)-5H-[1,2,4]triazolo[3,4-a]isoindol-5-one (X), 1,4-dihydroquinoxaline-2-carbonyl)-N-substituted hydrazine carbothioamide (XIXII), 5‑(3-amino-1,4-dihydroquinoxalin-2-yl)-4-substituted-4H-1,2,4-triazole-3-thiol (XIIIXIV) and 5-(3-amino-1,4-dihydroquinoxalin-2-yl)-N-substituted-1,3,4-thiadiazol-2-amine (XVXVI) based on 1,4-dihydroquinoxaline moiety in 60–85% yields starting from reaction of hydrazide 3-Amino-1,4-dihydroquinoxaline-2‑carbohydrazide (I) with ethyl acetoacetate has been proposed. The designed compounds have been successfully screened in vitro for their antibacterial and antifungal activities. Structural identifications of the obtained products have been carried out by spectroscopic techniques including FTIR, 1H NMR, 13C NMR, and mass spectroscopy. The relation between the structure of the synthesized compounds and their activity against selected bacteria and fungi was studied and favorable results were obtained. The majority of tested compounds showed moderate antibacterial activities except compound 3-amino-N-(2-(4-chlorophenyl)-4-oxothiazolidin-3-yl)-1,4-dihydroquinoxaline-2-carboxamide (VIII) that notably exhibited the most potent antibacterial activity against the tested Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa bacteria. Further antifungal studies indicated that the compounds Ethyl 3-(2-(3-amino-1,4-dihydroquinoxaline-2-carbonyl)hydrazono) butanoate (II), 3-amino-N-(2-(4-chlorophenyl)-4-oxothiazolidin-3-yl)-1,4-dihydroquinoxaline-2-carboxamide (VIII), 3-amino-N-(2-(4-methoxyphenyl)-4-oxothiazolidin-3-yl)-1,4-dihydro quinoxaline-2-carboxamide (IX) and 2-(3-amino-1,4-dihydroquinoxaline-2-carbonyl)-N-phenyl hydrazine carbothioamide (XI) exerted the highest antifungal activities against Aspergillus flavus and Candida albicans fungi.

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Funding

The financial support from Jouf University, Saudi Arabia, and Aswan University, Aswan, Egypt is gratefully acknowledged.

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Correspondence to Nadia Ali Ahmed Elkanzi.

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This article does not contain any studies involving human participants performed by any of the authors and does not contain any studies involving animals performed by any of the authors.

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The authors declare that they have no conflicts of interest.

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Corresponding author: e-mail: kanzi20@yahoo.com.

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Nadia Ali Ahmed Elkanzi, Hajer Hrichi Design and Evaluation of Antimicrobial Activity of New Pyrazole, 1,2,4-Triazole, and 1,3,4-Thiadiazol Derivatives Bearing 1,4-Dihydroquinoxaline Moiety. Russ J Bioorg Chem 46, 715–725 (2020). https://doi.org/10.1134/S1068162020050076

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  • DOI: https://doi.org/10.1134/S1068162020050076

Keywords:

  • pyrazole
  • quinoxaline
  • carbohydrazide
  • thiadiazoles
  • antibacterial
  • antifungal