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Eur J Med Chem. 2014 Oct 30;86:562-9. doi: 10.1016/j.ejmech.2014.09.017. Epub 2014 Sep 6.

Synthesis, in vitro cytotoxicity and apoptosis inducing study of 2-aryl-3-nitro-2H-chromene derivatives as potent anti-breast cancer agents.

Author information

1
Department of Medicinal Chemistry, Faculty of Pharmacy and Drug Design & Development Research Center, Tehran University of Medical Sciences, Tehran, Iran.
2
Department of Biotechnology, Iranian Research Organization for Science and Technology, Tehran 33535-111, Iran.
3
Institute of Biochemistry and Biophysics, Department of Biochemistry, University of Tehran, Tehran, Iran.
4
Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran.
5
Department of Medicinal Chemistry, Faculty of Pharmacy and Drug Design & Development Research Center, Tehran University of Medical Sciences, Tehran, Iran. Electronic address: ashafiee@ams.ac.ir.

Abstract

A series of 2-aryl-3-nitro-2H-chromenes 4a-u were designed as hybrid analogs of flavanone, β-nitrostyrene and nitrovinylstilbene scaffolds. They were synthesized from the reaction of appropriate β-nitrostyrenes and salicylaldehydes in good yields. In vitro cytotoxic activities of compounds 4a-u were tested against breast cancer cell lines including MCF-7, T-47D and MDA-MB-231. Most compounds exhibited good cytotoxic activity against selected cell lines, being more potent than standard drug etoposide. Representatively, 8-methoxy-3-nitro-2-(4-chlorophenyl)-2H-chromene (4l) with IC50 = 0.2 μM against MCF-7 cells, was 36-times more potent than etoposide. Apoptosis as a mechanism of cell death for selected compounds 4h and 4l was confirmed morphologically by acridine orange/ethidium bromide double staining and TUNEL analysis, as well as caspase-3 activation assay.

KEYWORDS:

2H-chromene; Anti-cancer agents; Apoptosis; Caspase-3; β-Nitrostyrene

PMID:
25216378
DOI:
10.1016/j.ejmech.2014.09.017
[Indexed for MEDLINE]

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