Synthesis of disulfide esters of dialkylaminocarbothioic acid as potent, non-detergent spermicidal agents.
Anil Kumar Dwivedi, Vishnu Lal Sharma, Niharika Kumaria, S T V S Kiran Kumar, Pradeep Kumar Srivastava, Abdul Haq Ansari, Jagdamba Prasad Maikhuri, Gopal Gupta, Janak Dulari Dhar, Raja Roy, Bhawani Shankar Joshi, Praveen Kumar Shukla, Manish Kumar, Satyawan Singh
Division of Pharmaceutics, CDRI, Lucknow, India. a_k_dwivedi@yahoo.com
Bioorganic & medicinal chemistry 2007 Nov 1S,S'-[disulfanediylbis(dialkylaminopropane-2,1-diyl)]bis- (dialkylaminothiocarbamate) (14-31) were prepared and evaluated for the spermicidal activity and antifungal activity. Dialkyldithiocarbamates (1-5) were reacted with epichlorohydrin to give 1-dialkylaminocarbothioic acid S-[(2,3-epithio)propyl]ester (7-11), these on further reaction with a secondary amine gave S,S'-[disulfanediylbis(dialkylaminopropane-2,1-diyl)]bis- (dialkylaminothiocarbamate) (14-31). Some of these compounds (16, 19-21, 23, 30, 31) were found to be very potent spermicidal agents with marginal antifungal activity. Two compounds (20, 21) were 25 times more active than nonoxynol-9 (N-9), the spermicide currently in the market.
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Anil Kumar Dwivedi, Vishnu Lal Sharma, Niharika Kumaria, S T V S Kiran Kumar, Pradeep Kumar Srivastava, Abdul Haq Ansari, Jagdamba Prasad Maikhuri, Gopal Gupta, Janak Dulari Dhar, Raja Roy, Bhawani Shankar Joshi, Praveen Kumar Shukla, Manish Kumar, Satyawan Singh. Synthesis of disulfide esters of dialkylaminocarbothioic acid as potent, non-detergent spermicidal agents. Bioorganic & medicinal chemistry. 2007 Nov 1;15(21):6642-8
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PMID: 17765548
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