Synthesis and Anticancer Activity of 3,4-Diaryl-1,2-dihydro- and 1,2,3,4-Tetrahydroquinolines

Author:

Rajput Santosh1,Falasca Valerio1ORCID,Bhadbhade Mohan2,Black David StC1ORCID,Kumar Naresh1ORCID

Affiliation:

1. School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia

2. Solid State and Elemental Analysis Unit, Mark Wainwright Analytical Centre, The University of New South Wales, Sydney, NSW 2052, Australia

Abstract

Tetrahydroquinolines are key structures in a variety of natural products with diverse pharmacological utilities and other applications. A series of 3,4-diaryl-5,7-dimethoxy-1,2,3,4-tetrahydroquinolines were synthesized in good yield by reacting 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones with different Grignard reagents followed by the dehydration of the intermediate phenolic compounds. Subsequent reduction and deprotection were carried out to achieve the desired tetrahydroquinolone moiety. The lead compound 3c showed low micromolar inhibition of various cancer cell lines. Demethylation under different reaction conditions was also investigated to afford the corresponding monohydroxy analogues.

Publisher

MDPI AG

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