Synthesis and pharmacology of the potent angiotensin-converting enzyme inhibitor N-[1 (S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanyl-(S)-pyroglutamic acid

AL Johnson, WA Price, PC Wong…

Index: Johnson, Alexander L.; Price, William A.; Wong, Pancras C.; Vavala, Robert F.; Stump, John M. Journal of Medicinal Chemistry, 1985 , vol. 28, # 11 p. 1596 - 1602

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Citation Number: 30

Abstract

Structure 3a, a potent angiotensin-converting enzyme inhibitor, was prepared in five steps from L-(+)-a-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 ita ability to inhibit converting enzyme and lower ...

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