Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Introduction of Heterocycles at the 2-Position of Indoline as Ester Bioisosteres

  • Lee, Sung-Kyung (Medicinal Science Division, Korea Research Institute of Chemical Technology) ;
  • Yi, Kyu-Yang (Medicinal Science Division, Korea Research Institute of Chemical Technology) ;
  • Yoo, Sung-Eun (Medicinal Science Division, Korea Research Institute of Chemical Technology)
  • Published : 2004.02.20
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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 ($K_{ATP}$). 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, ${\beta}$-hydroxy amide, hydrazide, nitrile starting from N-Boc-indoline-2-carboxylic acid.

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References

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