Carbodithioic acid esters of fluoxetine, a novel class of dual-function spermicides

Carbodithioic acid esters of fluoxetine have been prepared by replacing the methylamino function in aminopropane chain with carbodithioic acid ester group and by adding various S-2-hydroxypropyl ester of dialkyl carbodithioic acid at 3-methylamino group. Some of these compounds showed spermicidal, antifungal and anti-Trichomonas activities. The study revealed that incorporation of carbodithioic acid residue directly into fluoxetine structure leads to compounds with better antifungal and anti-Trichomonas activities, and N-methyl-[3-phenyl-3-(4-trifluoromethyl-phenoxy)-propyl]carbodithioic acid S-(2-pyrrolidino-ethyl) ester (14) has shown better profile than both fluoxetine and nonoxynol-9. Further lead optimization may yield a potent dual-function spermicide.

Graphical abstractCarbodithioic acid esters of fluoxetine prepared by replacing the methylamino function in aminopropane chain with carbodithioic acid group and by adding various S-2-hydroxypropyl ester of dialkylamino carbodithioic acid at 3-methylamino group have shown good spermicidal, antifungal and anti-Trichomonas activities.Figure optionsDownload full-size imageDownload as PowerPoint slide