Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Synthesis and Pharmacological Evaluation of New 1-Hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines as Norepinephrine Potentiators
Miyuki Ikeuchi, Masako Ikuta, Miyuki Hariki, Motoki Ikeuchi, Shigeki Maruyama, Mari Nakase, Kumiko Sakamoto, Yasuko Yoshioka, Aiko Yamauchi, Masaru Kihara
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Keywords: norepinephrine potentiator, norepinephrine reuptake inhibitor, 3-benzazepine, Barbier reaction, N-(phenylethyl)phenacylamine
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2009 Volume 57 Issue 5 Pages 443-445

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Abstract

4-Hydroxy-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline (PI-OH) (1a) and its derivatives form a new class of compounds which possess norepinephrine (NE) potentiating activity. As a new series of compounds, 1-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines (2a—f) were synthesized by the intramolecular Barbier reaction of N-[2-(2-iodophenyl)ethyl]phenacylamines (6a—f) with n-BuLi as a key reaction step. The potentiating activities of the benzazepines 2a—f on the contraction of rat anococcygeus muscle induced by NE were tested. Among the compounds tested in this study, compound 2a showed moderate potentiating activity (the activity ratio was 7.3-fold at 3×10−5 M).

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© 2009 The Pharmaceutical Society of Japan
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