Synthesis of 2amino4hthiazolo5,4bindole and characterization of its colored conversion products with protein tyrosine phosphatase inhibitory activity

In DMSOsolution 2amino4Hthiazolo5,4bindole is converted into a complex mixture of colored products. The three major conversion endproducts, 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 2amino4Hthiazolo5,4bindole as well as its Nacetyl derivatives prepared from either oxindole or 2bromo12nitrophenylethanone is described.