Today, there is an urgent need of safe and effective dual purpose contraceptive agents which can combinedly prevent unintended pregnancies and sexually transmitted infections. 4-hydroxy coumarins is an active pharmacophore in many naturally occurring antimicrobials or antibiotics such as Novobiocin, coumermycin and chlorobiocin etc. Here we report the synthesis of novel coumarin analogues and their biological evaluation as spermicide along with antimicrobial actions. The synthesis was achieved by the mannich type reaction between 4-hydroxy coumarin and substituted phenyl glyoxal in the presence of cyclic amines in good yields. A series of 32 compounds were synthesized. All the synthesized compounds were characterized by mass, IR , 1H and 13C NMR spectral data. These compounds were evaluated for spermicidal activity and then further screened against different strains of Trichomonas vaginalis for antimicrobial activity, HeLa cell lines for cytotoxicity and Lactobacillus jensenii for eco-safety. Some of the analogues were found more active and less cytotoxic than the reagent in the current clinical use Nonoxynol-9 (N-9).These compounds on contact with human spermatozoa, either destroy them or inhibit their normal function on very low concentration (upto 0.5 mM) with greater than 95% sperm immobilization and without inducing any cytotoxicity to normal cells. They were also found to have promising antimicrobial activity. All of the compounds were found highly safe in comparison of N-9 on HeLa and lactobacillus jensenii strains.

Design and synthesis of novel coumarin analogues by Mannich type reaction for spermicidal and anti microbial actions: A dual approach for contraception

251st National Meeting (2016)

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