Synthesis of New N,N'-Bis(5-arylidene-4-oxo-4,5-dihydrothiazolin-2-yl)piperazine Derivatives Under Microwave Irradiation and Preliminary Biological Evaluation

Sci Pharm. 2012 Oct-Dec;80(4):825-36. doi: 10.3797/scipharm.1206-04. Epub 2012 Sep 16.

Abstract

New N,N'-bis(5-arylidene-4-oxo-4,5-dihydrothiazoline-2-yl)diamine derivatives 5 were prepared in two steps from rhodanine and piperazine, or 1,4-bis(3-amino-propyl)piperazine, under microwave reaction conditions with retention of configuration. Some of these compounds were tested for in vitro antiproliferative activities and for their kinase inhibitory potencies towards six kinases (CDK5/p25, GSK3α/β, DYRK1A, DYRK2, CLK1, and CLK2). The compound 5d showed nanomolar activity towards DYRK1A kinase (IC(50) = 0.041 μM).

Keywords: 2,2’-(Piperazine-1,4-diyl)bis(5-benzylidene-1,3-thiazol-4(5H)-one); 5-Arylidene rhodanine; Cytotoxity; Diamines; Microwave irradiation; Protein kinase.