Synthesis and SAR studies for the inhibition of TNF-alpha production. Part 2. 2-[3-(Cyclopentyloxy)-4-methoxyphenyl]-substituted-1-isoindolinone derivatives

This study describes the synthesis and in vitro evaluation of 2-[3-(cyclopentyloxy)-4-methoxyphenyl]-1-isoindolinone derivatives substituted on benzene moiety of isoindoline ring for the inhibition of TNF-alpha production. From this study, we have found the 6-C position on isoindolinone ring is an o...

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Bibliographic Details
Published in:Archives of pharmacal research 2002-04, Vol.25 (2), p.137-142
Main Authors: Park, Joon Seok, Moon, Seong Cheol, Baik, Kyong Up, Cho, Jae Youl, Yoo, Eun Sook, Byun, Young Seok, Park, Myung Hwan, Balk, Kyung Up
Format: Article
Language:English
Subjects:
Animals
Indoles - chemical synthesis
Indoles - pharmacology
Mice
Structure-Activity Relationship
Tumor Necrosis Factor-alpha - antagonists & inhibitors
Tumor Necrosis Factor-alpha - biosynthesis
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Summary:This study describes the synthesis and in vitro evaluation of 2-[3-(cyclopentyloxy)-4-methoxyphenyl]-1-isoindolinone derivatives substituted on benzene moiety of isoindoline ring for the inhibition of TNF-alpha production. From this study, we have found the 6-C position on isoindolinone ring is an optimal derivatization site. Among the compounds synthesized, 6-amino-2-[3-(cyclopentyloxy)-4-methoxyphenyl]-1-isoindolinone (6) was the most potent in inhibitory activity of TNF-alpha production in LPS-stimulated RAW264.7 cells.
ISSN:0253-6269
1976-3786
DOI:10.1007/bf02976553