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Alternative Synthesis and Structural Analysis of the Antioxidant and Antitumor Agent 2-(3,5-Dimethoxyphenyl)-2,3-Dihydroquinolin-4(1H)-One

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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.

Graphic Abstract

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.

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Acknowledgements

The authors wish to acknowledge Laurie Lytle from Grove City College and Professor Gary Balaich of the U.S. Air Force Academy for his determination of the elemental analysis.

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Authors and Affiliations

  1. Department of Chemistry, Grove City College, 100 Campus Drive, Grove City, PA, 16127, USA

    Christopher S. Parry, Matthew D. Grossmann, Amy Thomas & Charles E. Kriley

  2. Department of Chemistry, Hamilton College, 198 College Hill Road, Clinton, NY, 13323, USA

    Max M. Majireck

  3. Rigaku Americas Corporation, 9009 New Trails Drive, The Woodlands, TX, 77381, USA

    Eric W. Reinheimer

Authors
  1. Christopher S. Parry
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  2. Matthew D. Grossmann
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  3. Amy Thomas
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  4. Max M. Majireck
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  6. Charles E. Kriley
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Correspondence to Charles E. Kriley.

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Parry, C.S., Grossmann, M.D., Thomas, A. et al. Alternative Synthesis and Structural Analysis of the Antioxidant and Antitumor Agent 2-(3,5-Dimethoxyphenyl)-2,3-Dihydroquinolin-4(1H)-One. J Chem Crystallogr 52, 122–129 (2022). https://doi.org/10.1007/s10870-021-00888-z

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