Synthesis and in vitro trichomonicidal, giardicidal and amebicidal activity of N-acetamide(sulfonamide)-2-methyl-4-nitro-1H-imidazoles☆

Synthesis of nitro(benzo)thiazole acetamides and in vitro antiprotozoal effect against amitochondriate parasites Giardia intestinalis and Trichomonas vaginalis

“…20 Compounds 1 and 4 showed nanomolar giardicidal activity and very low cytotoxic effects (>1000 lM), having selectivity indexes of 8196 and 6622, respectively. The SI calculated for these compounds versus both protozoa was >>1000, this fact implies that 1 and 4 are selectively toxic against G. intestinalis than the mammalian cells.…”

Imidazole derivatives as possible microbicides with dual protection

“…On the other hand, compounds 2-8 exhibited moderate to appreciable anti-trichomonas activity but their spermicidal activity was negligible. However, 5-nitroimidazoles bearing an arylsulfonylmethyl group [21] and N-acetamide(sulfonamide)-2-methyl-4-nitro-1H-imidazoles [22] have been reported to exhibit substantial activity against T. vaginalis.…”

“…Previously, some attempts have been made to modify metronidazole structure with a view to improve microbicidal activities [21][22][23]. Accordingly, the authors were prompted to carry out modifications in the structure of 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol (Metronidazole, 1, Scheme 1, the currently used drug for vaginal trichomoniasis [24]) with a view to introduce spermicidal activity.…”

“…Twenty three compounds (2,3,5,(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)28) exhibited antifungal activity at 25-50 mg/mL concentration. Seven compounds (9,18,19,22,24,26,28) 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 mg/mL concentration, whereas nonoxynol-9 (N-9, the marketed spermicidal microbicide) was highly cytotoxic.…”

“…Twenty six compounds were active against Trichomonas vaginalis at MIC ranging from 1-42 mM and seven compounds (9,18,19,22,24,26,28) immobilized 100% human spermatozoa at 1% concentration (w/v). Twenty three compounds (2,3,5,(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)28) exhibited antifungal activity at 25-50 mg/mL concentration. Seven compounds (9,18,19,22,24,26,28) showed significant anti-trichomonas and spermicidal activities and also exhibited mild antifungal activity.…”