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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 25, Number 2
BKCSDE 25(2)
February 20, 2004 

 
Title
Introduction of Heterocycles at the 2-Position of Indoline as Ester Bioisosteres
Author
Sunkyung Lee, Kyu Yang Yi*, Sung-eun Yoo
Keywords
N-Boc protection, Ester bioisostere, Indolin-2-yl-heterocycles
Abstract
In this study, we attempted to prepare compounds with heterocyclic replacements for metabolically unstable esters of benzopyranyl indole-2-carboxylic esters, which showed good in vitro and in vivo cardioprotective efficacies possibly through the opening of mitochondrial ATP-sensitive potassium channel (KATP). Initially, we tried to construct indolin-2-yl-heterocycles using unprotected indoline-2-carboxylic acid, but the cyclization was proceeded with oxidation of the indoline ring to the indole, which didn’t react with benzopyranyl epoxide. Thus we introduced N-Boc group to deplete the electron density of the indoline ring. We successfully prepared various indolin-2-yl-heterocycles by the cyclization of the building blocks including carboxamide, β-hydroxy amide, hydrazide, nitrile starting from N-Boc-indoline-2-carboxylic acid.
Page
207 - 212
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