- Synthesis of 2-amino-4H-thiazolo[5,4-b]indole and characterization of its colored conversion products with protein tyrosine phosphatase inhibitory activity
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In DMSO-solution 2-amino-4H-thiazolo[5,4-b]indole is converted into a complex mixture of colored products. The three major conversion end-products, of which two are inhibitors of protein tyrosine phosphatases (PTPs), were isolated by chromatographic methods and their structures characterized by spectroscopic analysis, including NMR and MS combined with computer assisted structure elucidation, and, finally, confirmed by independent chemical synthesis. Synthesis of 2-amino-4H-thiazolo[5,4-b]indole as well as its N-acetyl derivatives prepared from either oxindole or 2-bromo-1-(2-nitro-phenyl)ethanone is described.
- Breinholt,Jeppesen,Branner,Olsen,Moller,Nielsen,Andersen
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p. 569 - 577
(2007/10/03)
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- A convenient synthesis of 1,2-dihydro-3H-indol-3-ones and 1,2-dihydro-2H-indol-2-ones by Baeyer-Villiger oxidation
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The Baeyer-Villiger rearrangement of substituted 1H-indole-3-carbaldehydes afforded the corresponding substituted 1,2-dihydro-3H-indol-3-ones. The influence of 3-carbonyl and 1-protecting groups has been examined. Reaction has been extended to 1H-indole-2-carbaldehydes and used for synthesis of 1-(phenylsulfonyl)-1H-indol-2-yl trifluoromethanesulfonate.
- Bourlot,Desarbre,Merour
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p. 411 - 416
(2007/10/02)
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