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Synthetic study on novel immunosuppressant KF20444

The two new synthetic routes to 6,7-dihydro-10-fluoro-3-(2-fluorophenyl)-5 H- benzo[6,7]cyclohepta[1,2- b]-quinoline-8-carboxylic acid ( 1), a novel immunosuppressant KF20444, are described. The seven-membered ring construction from 2-[4-(2-fluorophenyl)phenyl]-3-(2-carboxyethyl)-4-chloromethyl-6-fl...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2001-12, Vol.9 (12), p.3273-3286
Main Authors: Chujo, Iwao, Masuda, Yoshiaki, Fujino, Kenji, Kato, Sachiko, Ogasa, Takehiro, Mohri, Shin-ichiro, Kasai, Masaji
Format: Article
Language:English
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Summary:The two new synthetic routes to 6,7-dihydro-10-fluoro-3-(2-fluorophenyl)-5 H- benzo[6,7]cyclohepta[1,2- b]-quinoline-8-carboxylic acid ( 1), a novel immunosuppressant KF20444, are described. The seven-membered ring construction from 2-[4-(2-fluorophenyl)phenyl]-3-(2-carboxyethyl)-4-chloromethyl-6-fluoroquinoline ( 17c) was achieved by intramolecular Friedel–Crafts reaction under acidic conditions as the key step. Subsequently, the oxidation of 4-chloromethyl group followed by reduction of carbonyl group on the seven-membered ring afforded 1. This route provides a new method for the synthesis of 1. A new synthetic route of KF20444, a novel immunosuppressant, is described. The seven-membered ring construction from 2-phenyl-3-(2-carboxyethyl)-4-chloromethylquinoline derivative was achieved by intramolecular Friedel–Crafts reaction as the key step.
ISSN:0968-0896
1464-3391
DOI:10.1016/S0968-0896(01)00238-3