Synthesis, urease inhibition and antimicrobial activities of some chiral 5-aryl-4-(1-phenylpropyl)-2H-1,2,4-triazole-3(4H)-thiones

Abstract

The synthesis of some chiral 5-aryl-4-(1-phenylpropyl)-2H-1,2,4-triazole- 3(4H)-thiones (6a-i) was carried out by cyclodehydration of 1-aroyl-4-(1- phenylpropyl)thiosemicarbazides (5a-i) obtained by the condensation of isomeric halo benzoic acid hydrazides (3a-i) and (R)-(+)-1-phenylpropyl isothiocyanate (4). The hydrazides (3a-i) were synthesized from the corresponding halo benzoic acids (1a-i) via esterification. The synthesis was confirmed by spectroanalytical techniques. The compounds 6d and 6e were found to be more potent urease inhibitors than the standard thiourea, depicting the IC 50 values of 7.8 ± 0.2 and 12.4 ± 0.2 μM, respectively (IC50 of thiourea = 21.0 ± 0.1 μM). Compounds 6c and 6h also exhibited very good urease inhibition activity with the IC 50 values of 35.9 ± 0.7 and 31.1 ± 0.5 μM, respectively. In addition the antimicrobial activities of the synthesized compounds are also being reported.