The 3-methyl-substituted analog (+/-)-3 of the angiotensin converting enzyme inhibitor A58365A (1) was synthesized from lactone 4 and amino acid ester 16, via key intermediates 18, 19 and 21a,b. Compound (+/-)-3 was found to possess powerful ACE inhibitory activity (IC 5 0 <space>=<space>ca 500<space>nM), as judged by in vitro tests against porcine kidney ACE, under conditions in which the commercial drug captopril has IC 5 0 <space>=<space>280<space>nM.
Le compose (+/-)-3, un analogue de l inhibiteur de l enzyme de conversion d angiotensine (ACE) A58365A (1), substitue par un methyle en position 3, a ete synthetise a partir de la lactone 4 et de l ester de l acide amine 16 via les intermediaires cles 18, 19 et 21a,b. Le compose (+/-)-3 a demontre une forte activite inhibitrice de l ACE renale porcine in vitro (IC 5 0 d environ 500<space>nM)<space>; dans les memes conditions, le captopril commercial demontre un IC 5 0 <space>=<space>280<space>nM.