Design, Synthesis, and Bioactivity Evaluation of Novel Sulfone Derivatives Incorporating an 1,2,4-Triazole Moiety

Abstract

Herein, a series of novel sulfone derivatives incorporating an 1,2,4-triazole moiety was synthesized and their structures were confirmed by ¹H NMR, ¹³C NMR, and HRMS. The in vitro antibacterial activities of these compounds against Wickerhamomyces anomalus (Wa) and Bacillus cereus (Bc) at concentrations of 200 and 100 μg/mL were evaluated using the turbidimeter tests. The results demonstrated that the target compounds exhibited moderate to good antibacterial activities against Wa and Bc. Notably, 3-{[(4-chlorophenyl)sulfonyl]methyl}-5-[(4-fluorobenzyl)thio]-4-methyl-4H-1,2,4-triazole showed excellent in vitro antibacterial activity against Bc at 200 μg/mL, with a 100% inhibition rate. Additionally, the in vitro antifungal activities of these compounds against Penicillium sumatraense (Ps) and Aspergillus fumigatus (Af) were assessed using the mycelium growth rate method. Bioassay results indicated that the target compounds exhibited certain antifungal activities against Ps and Af at 50 μg/mL. Specifically, 3-{[(4-chlorophenyl)sulfonyl]methyl}-4-phenyl-5-(propylthio)-4H-1,2,4-triazole displayed moderate antifungal activity against Ps at 50 μg/mL, with an inhibition rate of 64.52%. To the best of our knowledge, this study is the first to report on the synthesis and bioactivity evaluation of this series of novel sulfone derivatives incorporating an 1,2,4-triazole moiety.