Synthesis of 2-amino-4H-thiazolo[5,4-b]indole and characterization of its colored conversion products with protein tyrosine phosphatase inhibitory activity

Citation
J. Breinholt et al., Synthesis of 2-amino-4H-thiazolo[5,4-b]indole and characterization of its colored conversion products with protein tyrosine phosphatase inhibitory activity, J HETERO CH, 38(3), 2001, pp. 569-577
Citations number
21
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022-152X → ACNP
Volume
38
Issue
3
Year of publication
2001
Pages
569 - 577
Database
ISI
SICI code
0022-152X(200105/06)38:3<569:SO2ACO>2.0.ZU;2-F
Abstract
In DMSO-solution 2-amino-4H-thiazolo[5,4-b]indole is converted into a compl ex mixture of colored products. The three major conversion end-products, of which two are inhibitors of protein tyrosine phosphatases (PTPs), were iso lated by chromatographic methods and their structures characterized by spec troscopic analysis, including NMR and M:S combined with computer assisted s tructure elucidation, and, finally, confirmed by independent chemical synth esis. 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)eth anone is described.