Bulletin of the Korean Chemical Society

  • 제25권2호
  • /
  • Pages.207-212
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  • 2004
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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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)
  • 발행 : 2004.02.20
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초록

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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참고문헌

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  2. Chemo‐ and Enantioselective Hydrogenation of α‐Formyl Enamides: An Efficient Access to Chiral α‐Amido Aldehydes vol.131, pp.33, 2004, https://doi.org/10.1002/ange.201905263
  3. Chemo‐ and Enantioselective Hydrogenation of α‐Formyl Enamides: An Efficient Access to Chiral α‐Amido Aldehydes vol.58, pp.33, 2004, https://doi.org/10.1002/anie.201905263