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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 52, 2022 - Issue 17
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Articles

Synthesis and anticancer activity of oxazolo and oxazinoquinolinone derivatives

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Pages 1756-1767 | Received 25 May 2022, Published online: 22 Aug 2022
 

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

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