Synthesis of disulfide esters of dialkylaminocarbothioic acid as potent, non-detergent spermicidal agents

S,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.

Disulfide esters of dialkylaminocarbothioic acid (I; 14–31) were prepared and evaluated for the spermicidal activity and antifungal activity. Two compounds (20, 21) were 25 times more active than nonoxynol-9 (N-9), the spermicide currently in the market.Figure optionsDownload as PowerPoint slide