Synthesis of 5-substituted 2-oxazolidinethiones and their antagonism to uterotropic effect of diethylstilbestrol.

5-(4-Aminophenoxymethyl)-2-oxazolidinethiones were synthesized by the cyclization of 1-(4-aminophenoxy)-3-amino-2-propanol in the presence of potassium hydroxide and carbon disulfide. This oxazolidinethione, on reaction with suitable isothiocyanates, yielded 5-[4-(substituted thiocarbamido)phenoxymethyl]-2-oxazolidinethiones. These compounds antagonized the uterotropic effects of diethylstilbestrol in female rats and possessed approximate LD50 values of 400-greater than 800 mg/kg.