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.
D000818:Animals; D004054:Diethylstilbestrol / Q000037:antagonists & inhibitors*; D005260:Female; D009929:Organ Size / Q000187:drug effects; D010080:Oxazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D013329:Structure-Activity Relationship; D014599:Uterus / Q000187:drug effects*
D010080:Oxazoles; D004054:Diethylstilbestrol