- 5-Formyl salicylaldehyde as a linker for the synthesis of benzofuran containing insulin sensitivity enhancer compounds
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5-Formyl salicylaldehyde was prepared by treatment of 4-hydroxybenzaldehyde with HMTA in TFA. Reaction of this dialdehyde with α-haloacetyl aryl compounds gave 2,5-disubstituted benzofurans, from which an Insulin Sensitivity Enhancer compound was prepared.
- Stille, John R.,Ward, Jeffrey A.,Leffelman, Cindy,Sullivan, Kevin A.
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- Synthetic approaches to benzofuran containing Insulin Sensitivity Enhancer compounds for treatment of type II diabetes
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The search for Insulin Sensitivity Enhancer (ISE) compounds, for potential use in the treatment of Type II diabetes, has led to the synthesis of compounds that contain a benzofuran spacer between an aryloyl substituent and a 2,4-thiazolidinedione pharmacophore. Sequential combination of haloacetyl aryl substrates with 5-formylsalicylaldehyde gave the desired 2-aryloyl-5-formylbenzofuran intermediates. A related class of compounds, those with a methylene tether between the aromatic moiety and the benzofuran spacer, were also prepared through this strategy.
- Huff, Bret E.,Leffelman, Cindy L.,LeTourneau, Michael E.,Sullivan, Kevin A.,Ward, Jeffrey A.,Stille, John R.
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p. 1363 - 1384
(2007/10/03)
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