Discovery of novel carbazole derivatives containing a 1,3,4-thiadiazole moiety as antifungal candidates

作者：Chenghao Tang, Xingju Chen, Shengzhou Yang, Wenbo Guo, Xiumei Yang, Pei Li, Xiang Wang · 发表于：Phosphorus, sulfur, and silicon and the related elements · 年份：2023 · DOI：10.1080/10426507.2023.2191961 · 被引用次数：8 · 研究领域：Synthesis and biological activity、Fungal Plant Pathogen Control、Genomics, phytochemicals, and oxidative stress

Fifteen novel carbazole derivatives of 2-(9H-carbazol-9-yl)-N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide were designed, synthesized and evaluated for their antifungal activities against Pellicularia sasakii (P. sasakii), Fusarium oxysporum (F. oxysporum), Gibberella zeae (G. zeae), Phytophthora infestans (P. infestans), Cytospora mandshurica (C. mandshurica) and Capsicum wilt (C. wilt). The results of antifungal activity tests indicated that the inhibitory rates of compounds 2-(2-chloro-9H-carbazol-9-yl)-N-(5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl)acetamide (3h) and 2-(2-chloro-9H-carbazol-9-yl)-N-(5-(thiophen-2-yl)-1,3,4-thiadiazol-2-yl)acetamide (3o) against P. sasakii were 72.89% and 74.29%, respectively, which displayed better bioactivity compared with commercial fungicides hymexazol (53.09%) and carbendazim (69.65%). Meanwhile, compounds 2-(9H-carbazol-9-yl)-N-(5-(thiophen-2-yl)-1,3,4-thiadiazol-2-yl)acetamide (3f) and 2-(3-iodo-9H-carbazol-9-yl)-N-(5-(p-tolyl)-1,3,4-thiadiazol-2-yl)acetamide (3 l) exhibited the inhibition rates of 72.40% and 67.65% against C. wilt, respectively, which were better than the commercial fungicides hymexazol (50.21%) and carbendazim (65.33%).