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Synthesis and Antimicrobial Activity Evaluation of Imidazole‐Fused Imidazo[2,1‐ b ][1,3,4]thiadiazole Analogues
Author(s) -
Yan Guo Fang,
Ji Zheng Chang,
Wang Meiyuan,
Ai Jiangping,
Ying Han Lan,
Yang Liu,
Fang Lu Ye,
Xuan Yang Yu,
Guan Piao Ming,
Piao HuRi,
Jin ChunMei,
Jin Cheng Hua
Publication year - 2021
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.202100122
Subject(s) - chemistry , candida albicans , antimicrobial , cytotoxicity , corpus albicans , imidazole , stereochemistry , antibacterial activity , microbiology and biotechnology , bacteria , biochemistry , in vitro , organic chemistry , biology , genetics
Three series of new imidazole‐fused imidazo[2,1‐ b ][1,3,4]thiadiazole analogues (compounds 20 a – g , 21 a – g , and 22 a – g ) have been synthesized, and their antibacterial and antifungal activities have been evaluated. All the target compounds showed strong antifungal activity and high selectivity for the test fungus Candida albicans over Gram‐positive and ‐negative bacteria. N ‐((4‐(2‐Cyclopropyl‐6‐(4‐fluorophenyl)imidazo[2,1‐ b ][1,3,4]thiadiazol‐5‐yl)‐5‐(6‐methyl‐pyridin‐2‐yl)‐1 H ‐imidazol‐2‐yl)methyl)aniline ( 21 a ) showed the highest activity against C. albicans (MIC 50 =0.16 μg/mL), 13 and three times that of the positive control compounds gatifloxacin and fluconazole, respectively. Compounds 21 a and 20 e did not show cytotoxicity against human foreskin fibroblast‐1 cells, and compound 21 a was as safe as the positive control compounds in hemolysis tests. These results strongly suggest that some of the compounds produced in this work have value for development as antifungal agents.