Novel Triazolo-Tagged (Trifluoromethyl)quinazolin-4(3H)-one Derivatives and Their Anticancer Activity

A series of novel triazolo-tagged (trifluoromethyl)quinazolin-4(3H)-one derivatives were prepared starting from 2-aminobenzoic acid 1, which reacted with 4-chlorobenzoyl chloride to obtain 2-(4-chlorophenyl)-5-(trifluoromethyl)-4H-benzo[d][1,3]oxazin-4-one 2. A reaction between compound 2 and hydroxyl amine was then conducted to obtain 2-(4-chlorophenyl)-3-(4-hydroxyphenyl)-5-(trifluoromethyl)quinazolin-4(3H)-one 3, which further reacted with propargyl bromide to get 2-(4-chlorophenyl)-3-(prop-2-yn-1-yloxy)-5-(trifluoromethyl)quinazolin-4(3H)-one 4; finally, a reaction of compound 4 with aryl azide produced 1,2,3-triazole-functionalized quinazolinone derivatives 5a–5j. Upon evaluating all the final compounds for anticancer activity against four human cancer cell lines such as “HeLa—Cervical cancer (CCL-2); COLO 205—Colon cancer (CCL-222); HepG2—Liver cancer (HB-8065); MCF7—Breast cancer (HTB-22)”, compounds 5c, 5e, and 5f have been identified as promising.