1,2,4-Triazole-3-Thiones: Greener, One-Pot, Ionic Liquid Mediated Synthesis and Antifungal Activity

Abstract

Herein, we describe an efficient and rapid protocol for the synthesis of hitherto unreported 5-(benzothiazol-2-ylmethyl)-4-aryl-1,2,4-triazole-3-thiones by a one-pot condensation of 2-(benzothiazole-2-yl)acetohydrazide and aryl isothiocyanate in the presence of a base in the ionic liquid [bmim]Br. Among the eleven newly synthesized hybrid benzothiazolyl-triazole analogues, 5-(benzothiazol-2-ylmethyl)-4-(4-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (3d) displayed promising antifungal activity with MIC values of 12.5 and 0.39 μg/mL against the Aspergillus fumigatus and Candida albicans, respectively. Molecular docking studies employing CYP51 was also carried out to evaluate the binding mode of the most potent triazole derivative.

Keywords:

• Triazole
• benzothiazole
• ionic liquid
• antifungal

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This work was financially supported by the Deanship of Scientific Research, King Khalid University (Grant No. RGP. 1/136/42).