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Eur J Med Chem. 2014 Nov 24;87:150-8. doi: 10.1016/j.ejmech.2014.09.055. Epub 2014 Sep 17.

Design, regioselective synthesis and cytotoxic evaluation of 2-aminoimidazole-quinoline hybrids against cancer and primary endothelial cells.

Author information

1
Department of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar 125001, Haryana, India; Department of Chemistry, M.M. University, Mullana, Ambala 133207, Haryana, India.
2
Department of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar 125001, Haryana, India.
3
Laboratory of Nanotechnology and Chemical Biology, Regional Centre for Biotechnology, Gurgaon 122016, Haryana, India.
4
Department of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar 125001, Haryana, India. Electronic address: dk_ic@yahoo.com.
5
Department of Chemistry, M.M. University, Mullana, Ambala 133207, Haryana, India.

Abstract

In search of new selective anti-cancer agents, a series of sixteen novel 2-aminoimidazole-quinoline hybrid compounds (5a-5p) have been designed and synthesized regioselectively. We have characterized the compounds extensively using IR, 1D and 2D NMR Spectroscopy and mass spectrometry. The cytotoxicity studies against different cancer cell lines showed that the compound 5a (Imd-Ph) emerged as a potent cytotoxic scaffold. Imd-Ph (5a) exhibited a selective anticancer activity against human colon cancer cell line (HCT-116, DLD-1) and was found relatively non-toxic to breast cancer cells (MDA-MB-231) as well as to normal primary endothelial cells (HUVEC). Structure-activity relationship of imidazole-quinoline hybrid scaffolds revealed differential and selective toxicities exerted by the different derivatives against cancer and normal cells. Structural modification of the scaffold with library of a wide variety of substituents may lead to the development of novel selective anti-cancer agents in the future.

KEYWORDS:

2-Aminoimidazole; Cytotoxicity; Quinoline; Regioselectivity; Selective anticancer agents

PMID:
25247771
DOI:
10.1016/j.ejmech.2014.09.055
[Indexed for MEDLINE]

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