Conformational analysis of Ramipril (HOE 498) in a solution by NMR

Conformations of Ramipril (Hoe 498, 2-[ N-(S)-1-ethoxycarbonyl-3-phenylpropyl]-L-alanyl-(1S, 3S, 5S)-2-azabicyclo (3,3,0) octane-3-carboxylic acid), a non-sulfhydryl angiotensin I converting enzyme (ACE) inhibitor, were investigated in CD 3OD, to account for their specific biological activity and lo...

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Bibliographic Details
Published in:Journal of molecular structure 1991-05, Vol.245 (3), p.379-389
Main Authors: Sakamoto, Yohko, Ishii, Tomoko, Oonishi, Isao, Ohmoto, Taichi
Format: Article
Language:English
Subjects:
Biological and medical sciences
General pharmacology
Medical sciences
Pharmacology. Drug treatments
Physicochemical properties. Structure-activity relationships
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Summary:Conformations of Ramipril (Hoe 498, 2-[ N-(S)-1-ethoxycarbonyl-3-phenylpropyl]-L-alanyl-(1S, 3S, 5S)-2-azabicyclo (3,3,0) octane-3-carboxylic acid), a non-sulfhydryl angiotensin I converting enzyme (ACE) inhibitor, were investigated in CD 3OD, to account for their specific biological activity and long-lasting effectiveness. The preferred optimum structures of the cis and trans forms are postulated. The identification of the two conformers is based on NMR measurements and classical energy calculations. The cis conformation should be preferred for biological activity.
ISSN:0022-2860
1872-8014
DOI:10.1016/0022-2860(91)87112-U