Quinoline-based compounds are one of the most important classes of N-heterocyclics exhibiting a wide spectrum of biological activities. There is a constant demand for the synthesis of new quinoline-based molecules suitable for therapeutic applications. Here a new strategy is developed to synthesize different quinoline-based quinazolinones catalytically using InCl 3 through a cyclocondensation reaction of isatoic anhydride and aniline with 2-substituted-quinoline-3-carbaldehyde to produce 2-(2-phenoxyquinolin-3-yl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one derivatives (> 90 % yields). In contrast, the reduced electrophilicity at the metal center allows the hydrazide ligand to bind In(III) and serendipitously forms benzoic(2-phenoxyquinoline-3-carbonyl) carbamic anhydride (∼ 70 % yields). The mechanistic aspects of these reactions were rationally explained. The structure and purity of all the isolated derivatives were assessed by spectroscopic and analytical data. In view of a strong correlation existing between inflammation and cancer progression, the ex-vivo anti-inflammatory effect of the ligands was established. The anti-cancer property of the proposed ligand was delineated with a specific SIRT protein family. Further, the computational docking studies on the binding abilities of 22 synthesized compounds with the Sirt1 protein were discussed in detail.
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