Synthesis and antimicrobial activity of new thiazole and thiadiazole derivatives via ethyl pyruvate

ABSTRACT

Reaction of ethyl 2-(2-((methylthio)carbonothioyl)hydrazono)propanoate (2) and ethyl 2-(2-carbamothioyl-hydrazono)propanoate (3) with hydrazonoyl halides 4a-e afforded the corresponding thiadiazoles 5a-e. Also, treatment of compound 2 with α-ketohydrazonoyl halides 12a-f in absolute ethanol and in the presence of triethylamine gave the corresponding thiadiazoles 13a-f; while reaction of ethyl 2-(2-carbamothioyl-hydrazono)propanoate (3) with α-ketohydrazonoyl halide 12 gave thiazole derivatives 15. Also, the reaction of compound 3 with hydrazonoyl chloride 12f afforded thiazolone derivative 18. Antimicrobial studies are performed using two-gram positive bacteria and two-gram negative bacteria. Data revealed that thiazole derivative 17a achieved the lowest MIC values (high efficient derivative) against the sensitive bacterial strain S. aureus with MIC value 160 µg/ml.

GRAPHICAL ABSTRACT

KEYWORDS:

• Ethyl pyruvate
• thiosemicarbazide
• methyl hydrazinecarbodithioate
• hydrazonoyl halides
• thiadiazoles
• thiazoles

Disclosure statement

No potential conflict of interest was reported by the authors.

ORCID

Fatma M. Saleh http://orcid.org/0000-0003-0451-4802

Abdou O. Abdelhamid http://orcid.org/0000-0002-5380-7727

Hamdi M. Hassaneen http://orcid.org/0000-0003-0963-4192