Synthesis and pharmacology of the potent angiotensin-converting enzyme inhibitor N-[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanyl-(S)-pyroglutamic acid
- 31 October 1985
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 28 (11) , 1596-1602
- https://doi.org/10.1021/jm00149a009
Abstract
Structure 3a, a potent angiotensin-converting enzyme inhibitor, was prepared in five steps from L-(+)-.alpha.-amino-4-phenylbutyric acid by construction of the activated side-chain ester 16, displacement with L-pyroglutamate ester anion, and deblocking. Diastereomer separation was accomplished by chromatography at the diester stage, 17. Pharmacological assays established that 3a parallels enalapril in its ability to inhibit converting enzyme and lower blood pressure.This publication has 5 references indexed in Scilit:
- ANTIHYPERTENSIVE ACTIVITY OF N-[(S)-1-(ETHOXYCARBONYL)-3-PHENYLPROPYL]-L-ALA-L-PRO (MK-421), AN ORALLY ACTIVE CONVERTING ENZYME-INHIBITOR1981
- A new class of angiotensin-converting enzyme inhibitorsNature, 1980
- SQ 14,225 (D-3-MERCAPTO-2-METHYLPROPANOYL-L-PROLINE), A NOVEL ORALLY ACTIVE INHIBITOR OF ANGIOTENSIN I-CONVERTING ENZYME1978
- Design of potent competitive inhibitors of angiotensin-converting enzyme. Carboxyalkanoyl and mercaptoalkanoyl amino acidsBiochemistry, 1977
- THE METABOLISM OF GLUTARIC ACID-1,5-C-14 .1. IN NORMAL AND PHLORHIZINIZED RATS1952