Synthesis and screening for antioxidant and cytotoxic activities of novel 2-thioxo-benzo[f]chromeno[2,3-d]pyrimidin-4-ones derived by cetylpyridinium chloride catalyzed multicomponent reactions in aqueous micellar media

Abstract

The cetylpyridinium chloride (CPC) has been used as micellar catalyst in three-component one-pot reaction involving thiobarbituric acids, aromatic aldehydes and β-napthol for synthesizing the novel 2-thioxo-benzo[5,6]chromeno[2,3-d]pyrimidin-4-one derivatives in aqueous media. These 2-thioxo-benzo[5,6]chromeno[2,3-d]pyrimidin-4-one derivatives have been screened for antioxidant and cytotoxic activities. It has been found that 2-thioxo-5-(4-nitrophenyl)-benzo[f]chromeno[2,3-d]pyrimidin-4-one (4a) has shown highest scavenging activity value to reduce DPPH free radicals, which may be due to the presence of nitro group at para-position. Three compounds, 4a, 4b and 4o show significant in vitro antitumor activity. The study of the antioxidant and cytotoxic activities reveal that all the compounds show moderate to good activity indicating that the presence of thiouriedo linkage in the pyrimidine nucleus and the chromeno group attached to pyrimidene moiety are responsible for these activities.