Design and Evaluation of Antimicrobial Activity of New Pyrazole, 1,2,4-Triazole, and 1,3,4-Thiadiazol Derivatives Bearin
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esign and Evaluation of Antimicrobial Activity of New Pyrazole, 1,2,4-Triazole, and 1,3,4-Thiadiazol Derivatives Bearing 1,4-Dihydroquinoxaline Moiety Nadia Ali Ahmed Elkanzia, b, 1 and Hajer Hrichia, c aChemistry
Department, College of Science, Jouf University, P.O. Box: 2014, Sakaka, Saudi Arabia Chemistry Department, Faculty of Science, Aswan University, P.O. Box: 81528, Aswan, Egypt c National Institute of Applied Sciences and Technology, Carthage University, Centre Urbain Nord, B.P.No. 676, Tunis Cedex, 1080 Tunisia b
Received September 3, 2019; revised September 30, 2019; accepted October 1, 2019
Abstract—An effective method for synthesizing a series of fifteen new compounds ethyl 3-(2-(3-amino-1,4dihydroquinoxaline-2-carbonyl)hydrazono )butanoate (II), 3-amino-N'-benzylidene-1,4-dihydroquinoxaline-2-carbohydrazide dérivatives (IV–VI), phenyl)-4-oxothiazolidin-3-yl)-1,4-dihydroquinoxaline-2-carboxamide derivatives (VII–IX), 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 (XI–XII), 5-(3-amino-1,4-dihydroquinoxalin-2-yl)-4-substituted-4H-1,2,4-triazole-3-thiol (XIII–XIV) and 5-(3-amino1,4-dihydroquinoxalin-2-yl)-N-substituted-1,3,4-thiadiazol-2-amine (XV–XVI) based on 1,4-dihydroquinoxaline moiety in 60–85% yields starting from reaction of hydrazide 3-Amino-1,4-dihydroquinoxaline2-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)-4oxothiazolidin-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-1,4dihydroquinoxaline-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-2carbonyl)-N-phenyl hydrazine carbothioamide (XI) exerted the highest antifungal activities against Aspergillus flavus and Candida albicans fungi. Keywords: pyrazole, quinoxaline, carbohydrazide, thiadiazoles, antibacterial, antifungal DOI: 10.1134/S1068162020050076
INTRODUCTION The prevalence of microbial infections is expanding worldwide despite the progressive research dedicated to the design and development of
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