Synthesis and anticancer evaluation of 3-substituted quinolin-4-ones and 2,3-dihydroquinolin-4-ones

Santosh Rajput; Christopher R Gardner; Timothy W Failes; Greg M Arndt; David Stc Black; Naresh Kumar

doi:10.1016/j.bmc.2013.11.047

Synthesis and anticancer evaluation of 3-substituted quinolin-4-ones and 2,3-dihydroquinolin-4-ones

Bioorg Med Chem. 2014 Jan 1;22(1):105-15. doi: 10.1016/j.bmc.2013.11.047. Epub 2013 Dec 4.

Authors

Santosh Rajput¹, Christopher R Gardner¹, Timothy W Failes², Greg M Arndt², David Stc Black¹, Naresh Kumar³

Affiliations

¹ School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia.
² ACRF Drug Discovery Centre for Childhood Cancer, Children's Cancer Institute Australia for Medical Research, Lowy Cancer Research Centre, The University of New South Wales, Sydney, NSW 2052, Australia.
³ School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia. Electronic address: n.kumar@unsw.edu.au.

PMID: 24332654
DOI: 10.1016/j.bmc.2013.11.047

Abstract

A series of 3-aryl-5,7-dimethoxyquinolin-4-ones 8 and 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones 13 were synthesized in good yields. Demethylation under a range of conditions afforded the corresponding 5-hydroxy and 5,7-dihydroxy derivatives. Biological evaluation against a range of cancer cells lines showed that the quinolin-4-one scaffold was more cytotoxic than the reduced 2,3-dihydroquinolin-4-one scaffold. The most active monohydroxy compound 15f demonstrated 85.9-99% reduction in cell viability against the cell lines tested.

Keywords: Anticancer; Dihydroquinolin-4-one; Quinolin-4-one.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cell Line, Tumor
Humans
Molecular Structure
Quinolones / chemical synthesis*
Quinolones / chemistry
Structure-Activity Relationship

Substances

Quinolones