Design and synthesis of 3- (azol-1-yl) phenylpropanes as microbicidal spermicides for prophylactic contraception
Kumar, L.; Sarswat, A.; Lal, N.; Jain, A.; Kumar, S.; Kiran Kumar, S.T.V.S.; Maikhuri, J.P.; Pandey, A.K.; Shukla, P.K.; Gupta, G.; Sharma, V.L.
Bioorganic and Medicinal Chemistry Letters 21(1): 176-181
2011
ISSN/ISBN: 1464-3405 PMID: 21130651 DOI: 10.1016/j.bmcl.2010.11.042Document Number: 215195
We designed a series of 25 3-(azol-1-yl)phenylpropanes which yielded 10 compounds (3, 4, 7, 8, 13, 14, 19, 21, 23, 26) that irreversibly immobilized 100% human sperm at 1% (w/v) concentration in 60s; 12 compounds (8, 9, 15, 16, 19-21, 23-25, 27, 28) that showed potent microbicidal activity at 12.5-50 μg/mL against Trichomonas vaginalis; and 17 compounds (3-11, 13, 15, 19, 21, 23, 26, 28, 30) that exhibited potent anticandida activity with minimum inhibitory concentration (MIC) of 12.5-50 μg/mL. Almost all the compounds exhibited high level of safety towards normal vaginal flora (Lactobacillus) and human cervical (HeLa) cells in comparison to the marketed spermicide nonoxynol-9 (N-9). All the biological activities were evaluated in vitro. Two compounds (4, 8) with good safety profile exhibited multiple (spermicidal, antitrichomonas and anticandida) activities, warranting further lead optimization for furnishing a prophylactic vaginal contraceptive.
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