An expedient synthesis of novel 2-substituted thiazolo[4,5-f]isoquinolines/quinolines and benzo[1,2-d:4,3-d ']bisthiazoles and their potential as inhibitors of COX-1 and COX-2

Abstract

An efficient, general synthesis of 2-substituted thiazolo[4,5-f]isoquinolines, thiazolo[4,5-f]quinolines and benzo[1,2-d:4,3-d']bisthiazoles has been accomplished from 5-nitroisoquinoline/quinoline and 6-nitrobenzothiazole, respectively, and all the products have been thoroughly identified spectroscopically (IR, (1)H and (13)C NMR, LR/HR EI/FAB/ESI-MS). The synthesis of thiazolo[4,5-f]isoquinolines constitutes the first synthesis of this class of heteroarenes. Eighteen compounds, covering all three types, were screened for inhibition of COX-1 and COX-2, and some of them showed moderate activities.