Synthesis and hererocyclizations of 3,4-dihydroquinazolin-2-yl guanidine in the search of new anticancer agents

Abstract

The cyclocondensations of 3,4-dihydroquinazolin-2-yl guanidine with a variety of electrophilic reagents viz. aldehydes, ketones, triethyl orthoformate, diethyl ethoxymethylenemalonate, carbon disulfide and trichloroacetonitrile were found to afford l,3,5-triazino[2,l-b]quinazolin.However, some unexpected reactions were also observed. The structural properties such as tautomerism and hinderance to conformational rotation were also investigated. The results of biological testing suggested that the l,3,5-triazino[2,l-b]quinazolinenucleus could be a new promising scaffold for the development of potential anticancer agents. © 2009 The Japan Institute of Heterocyclic Chemistry All rights reserved.