STEROIDAL A-RING ARYL CARBOXYLIC-ACIDS - A NEW CLASS OF STEROID 5-ALPHA-REDUCTASE INHIBITORS

A series of 17β-carbamoyl-1,3,5(10)-estratriene-3-carboxylic acids has been prepared and evaluated in vitro as inhibitors of human and rat prostatic steroid 5α-reductase (EC 1.3.1.30). Potent inhibition of the human enzyme, in particular, was observed and preliminary studies using rat enzyme suggest that the inhibition results from the formation of an enzyme-NADP+-inhibitor complex. The compounds were synthesized from estrone, generally employing a differentiated bis-triflate carbonylation strategy. © 1990, American Chemical Society. All rights reserved.