Imidazole derivatives as possible microbicides with dual protection

Abstract

Twenty seven derivatives (2-28) of 2-(2-methyl-5-nitro-1H-imidazol-1-yl) ethanol were synthesized and evaluated for anti-trichomonas, spermicidal and antifungal activities. Twenty six compounds were active against Trichomonas vaginalis at MIC ranging from 1 – 42 µM and seven compounds (9, 18, 19, 22, 24, 26, and 28) immobilized 100% human spermatozoa at 1% concentration (w/v).Twenty three compounds (2, 3, 5, 8-26, 28) exhibited antifungal activity at 25-50 µg/mL concentration. Seven compounds (9, 18, 19, 22, 24, 26, and 28) showed significant anti-trichomonas and spermicidal activities and also exhibited mild antifungal activity. All the compounds were highly safe towards human cervical cell line (HeLa) as shown by the cell-viability assay of HeLa cells at 200 µg/mL concentration, whereas nonoxynol-9 (N-9, the marketed spermicidal microbicide) was highly cytotoxic. Therefore, it may be concluded that introduction of the pharmacophore responsible for spermicidal activity into a proven anti-trichomonas structure may lead to a potent dual function microbicide better and safer than N-9.