Synthesis and angiotensin converting enzyme-inhibitory activity of N-[(1S)-1-carboxy-5-(4-piperidyl)pentyl]-L-alanine derivatives.

doi:10.1248/CPB.42.580

Paper

Synthesis and angiotensin converting enzyme-inhibitory activity of N-[(1S)-1-carboxy-5-(4-piperidyl)pentyl]-L-alanine derivatives.

Published Mar 15, 1994 · M. Kori, K. Itoh, Y. Inada

Chemical & pharmaceutical bulletin

Q3 SJR score

4

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0

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Abstract

As part of a search for potent and long-lasting angiotensin converting enzyme (ACE) inhibitors, various types of N-[(1S)-1-carboxy-5-(4-piperidyl)pentyl]-L-alanine derivatives (7a, 8-11) were prepared. The key synthetic intermediate, N-[(1S)-5-(1-benzyloxycarbonyl-4-piperidyl)-1- ethoxycarbonylpentyl]-L-alanine (17a), was synthesized by asymmetric reduction of the alpha-oxoester (13) with Lactobacillus paracasei subsp. paracasei followed by a substitution reaction with tert-butyl L-alaninate (15) and subsequent treatment with hydrogen chloride. Compounds 7a and 8-11 showed potent and long-lasting ACE-inhibitory activity in rats.

Non-RCT

Animal Study

Study Snapshot

N-[(1S)-1-carboxy-5-(4-piperidyl)pentyl]-L-alanine derivatives show potent and long-lasting angiotensin converting enzyme (ACE) inhibitory activity in rats.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Synthesis and angiotensin converting enzyme-inhibitory activity of N-[(1S)-1-carboxy-5-(4-piperidyl)pentyl]-L-alanine derivatives.

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