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Facile synthesis of new quinazolinone benzamides as potent tyrosinase inhibitors: Comparative spectroscopic and molecular docking studies

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Abstract The simple reaction approach has been designed and utilized for the synthesis of quinazolinone benzamides 4a-4h using isatoic anhydride, m-Anisic hydrazide and various aldehydes. The formation of target compounds… Click to show full abstract

Abstract The simple reaction approach has been designed and utilized for the synthesis of quinazolinone benzamides 4a-4h using isatoic anhydride, m-Anisic hydrazide and various aldehydes. The formation of target compounds was confirmed by spectral characterization techniques such as IR, NMR, Mass and elemental analysis. The spectrophotometric investigations based on absorption and fluorescence outputs denote distinctive properties such as molar extinction coefficient, fluorescence emission, fluorescence lifetime, quantum yield and Stokes shift for compounds 4a-4h in three different solvents. Along with spectroscopic studies, synthesized compounds 4a-4h were tested for bioevaluation against tyrosinase inhibitory activity. Pleasingly, all compounds displayed lower IC50 values (0.006 ± 0.074 to 1.609 ± 0.324 μM) than standard kojic acid (16.832 ± 1.162  μM) against tyrosinase inhibition. The comparative spectrophotometric properties, in vitro and in silico analysis suggest that compounds 4d and 4f have significant absorption and fluorescence properties in addition to extremely low IC50 values as potent tyrosinase inhibitors.

Keywords: facile synthesis; tyrosinase inhibitors; quinazolinone benzamides; fluorescence; potent tyrosinase

Journal Title: Journal of Molecular Structure
Year Published: 2019

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