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

✍ Scribed by Jens Breinholt; Claus Bekker Jeppesen; Sven Branner; Carl Erik Olsen; Niels Peter Hundahl Møller; Bjarne Hilmer Nielsen; Henrik Sune Andersen

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2001
• Tongue: English
• Weight: 128 KB
• Volume: 38
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570380303

✦ Synopsis

Abstract

In DMSO‐solution 2‐amino‐4__H__‐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 phos‐phatases (PTPs), were isolated by chromatographic methods and their structures characterized by spectro‐scopic analysis, including NMR and MS combined with computer assisted structure elucidation, and, finally, confirmed by independent chemical synthesis. Synthesis of 2‐amino‐4__H__‐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.