Synthesis and anticancer activity of oxazolo and oxazinoquinolinone derivatives

Abstract

A convenient and efficient reduction of 3-nitro-4-hydroxy-1-methylquinolin-2(1H)-one using tin and hydrochloric acid produced the novel 3-amino-4-hydroxyquinolinone derivative. The aminoquinoline was reacted with various electrophilic reagents such as acid anhydrides, acyl chlorides and esters to give a tricyclic system namely; oxazoloquinolinone and oxazinoquinolinone. Diazotization and alkylation of aminoquinoline were carried out affording the interesting N-alkylated quinoline and azodye derivatives. Selected products were screened for their anticancer activity against HepG-2 and MCF-7 cell lines. Among the various synthesized derivatives, the aminoquinoline compound is the strong antiproliferative agent and may consider a specific therapeutic index.

Graphical Abstract

Keywords:

• Oxazoloquinoline
• reduction
• anticancer activity
• electrophiles
• cyclization