Paper
Alternative Synthesis and Structural Analysis of the Antioxidant and Antitumor Agent 2-(3,5-Dimethoxyphenyl)-2,3-Dihydroquinolin-4(1H)-One
Published 2021 · DOI · Christopher S. Parry, Matthew D. Grossmann, Amy Thomas
Journal of Chemical Crystallography
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Abstract
Herein we present the synthesis, structure and NMR and mass spectroscopic analyses of the antioxidant 2-(3,5-dimethoxyphenyl)-2,3-dihydroquinolin-4(1H)-one (1), a member of the 2-aryl-2,3-dihydroquinolin-4(1H)-one family of molecules that have been shown to display a range of potent biological properties. The title molecule, prepared by an alternative methodology to that recently reported, crystallizes in the centrosymmetric space group P21/c with unit cell dimensions a = 11.775(17) Å, b = 5.3592(8) Å, c = 22.462(3) Å and β = 96.576(11)°. Close analysis of the solid state structure reveals an array of weak N–H∙∙∙O hydrogen bonding as well as C–H∙∙∙O, and C–H∙∙∙π interactions between the neighboring molecules. The presence of 1 was also confirmed via NMR and mass spectroscopic analyses. Herein we present the solid state structure and results of mass spectroscopic and nuclear magnetic resonance analyses of the powerful antitumor compound 2-(3,5-dimethoxyphenyl)-2,3-dihydroquinolin-4(1H)-one prepared by an alternative synthetic avenue.
The alternative synthetic route for 2-(3,5-dimethoxyphenyl)-2,3-dihydroquinolin-4(1H)-one reveals a strong antitumor compound with potential for pharmaceutical applications.
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