Synthesis and biological evaluation of new 1,3,4-thiadiazole derivatives as potent antimicrobial agents

Author:

Kamel Monica G.,Sroor Farid M.,Othman Abdelmageed M.,Hassaneen Hamdi M.ORCID,Abdallah Tayseer A.,Saleh Fatma M.,Teleb Mohamed A. Mohamed

Abstract

AbstractA series of 1,3,4-thiadiazole derivatives were designed and synthesized using N-(4-nitrophenyl)acetohydrazonoyl bromide and 1-[3,5-dimethyl-1-(4-nitrophenyl)-1H-pyrazol-4-yl]ethan-1-one as starting materials. The treatment of 1-[3,5-dimethyl-1-(4-nitrophenyl)-1H-pyrazol-4-yl]ethan-1-one with methyl hydrazinecarbodithioate or hydrazinecarbothioamide afforded 2-[1-[5-methyl-1-(4-nitrophenyl)-1H-pyrazol-4-yl]ethylidene]hydrazine derivatives. The targeted 1,3,4-thiadiazolyl derivatives were prepared by the reaction of 2-[1-[5-methyl-1-(4-nitrophenyl)-1H-pyrazol-4-yl]ethylidene]hydrazine derivatives with hydrazonoyl chloride derivatives. The reaction of N-(4-nitrophenyl)acetohydrazonoyl bromide with 2-[(methylthio)carbonthioyl]hydrazones in absolute ethanol in the presence of triethylamine afforded the corresponding 1,3,4-thiadiazole derivatives. The newly synthesized compounds were fully characterized by 1H NMR, 13C NMR, IR, MS, and elemental analysis. Moreover, the antimicrobial activity of the synthesized 1,3,4-thiadiazole derivatives were tested against E. coli, B. mycoides, and C. albicans. Four compounds outperformed the other produced compounds in terms of antimicrobial activity. Graphical abstract

Funder

Cairo University

Publisher

Springer Science and Business Media LLC

Subject

General Chemistry

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