Design and synthesis of novel 1,3,4-thiadiazole thioglycosides as promising antimicrobial potent structures

Abstract

Thiosemicarbazide was used as a key starting material for the building of a diversity of novel heterocyclic moieties. The heterocyclization reaction of thiosemicarbazide derivatives with carbon disulfide in basic conditions afforded novel heterocyclic 1,3,4-thiadiazolethiolate derivatives. 1,3,4-thiadiazole-2-thiol was successfully reacted with protected α-D-gluco- and galacto-pyranosyl bromides in dimethylformamide at room temperature to give the matching 1,3,4-thiadiazole S-glycosides in good yields. The latter compounds were reacted with ammonia-methanol at room temperature for 10 min, and the deprotected derivatives were obtained in good yields. The newly synthesized compounds were characterized by basic analyses and spectral information (IR,¹H NMR, and ¹³C NMR, X-ray). All newly produced compounds were evaluated and screened for their antibacterial activities. Compound 6f proved to be the most active antimicrobial among the investigated heterocycles.

Keywords:

• Thiosemicarbazide
• 1,3,4-thiadiazolethiolates
• α-D-gluco- and galacto-pyranosyl bromides
• thiadiazole thioglycosides
• antibacterial agents

Acknowledgement

The authors express their gratitude to the Central Laboratory at Helwan University (CLHU) for conducting NMR analysis.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

The author(s) reported there is no funding associated with the work featured in this article.