2. Academic Validation
  3. Synthesis and anticancer activity of N-substituted 2-arylquinazolinones bearing trans-stilbene scaffold

Synthesis and anticancer activity of N-substituted 2-arylquinazolinones bearing trans-stilbene scaffold

  • Eur J Med Chem. 2015 May 5:95:492-9. doi: 10.1016/j.ejmech.2015.03.057.
Mohammad Mahdavi 1,  Keyvan Pedrood 2,  Maliheh Safavi 3,  Mina Saeedi 4,  Mahboobeh Pordeli 5,  Sussan Kabudanian Ardestani 5,  Saeed Emami 6,  Mehdi Adib 2,  Alireza Foroumadi 1,  Abbas Shafiee 7
Affiliations

Affiliations

  • 1 Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran.
  • 2 School of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran.
  • 3 Department of Biotechnology, Iranian Research Organization for Science and Technology, Tehran, Iran.
  • 4 Medicinal Plants Research Center, Tehran University of Medical Sciences, Tehran, Iran; Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran.
  • 5 Department of Biochemistry, Institute of Biochemistry and Biophysics, University of Tehran, Tehran, Iran.
  • 6 Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran.
  • 7 Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran. Electronic address: ashafiee@ams.ac.ir.
PMID: 25847767 DOI: 10.1016/j.ejmech.2015.03.057
Abstract

A novel series of 2-arylquinazolinones 7a-o bearing trans-stilbene moiety were designed, synthesized, and evaluated against human breast Cancer cell lines including human breast adenocarcinoma (MCF-7 and MDA-MB-231) and human ductal breast epithelial tumor (T-47D). Among the tested compounds, the sec-butyl derivative 7h showed the best profile of activity (IC50 < 5 μM) against all cell lines, being 2-fold more potent than standard drug, etoposide. Our investigation revealed that the cytotoxic activity was significantly affected by N3-alkyl substituents. Furthermore, the morphological analysis by acridine orange/ethidium bromide double staining test and flow cytometry analysis indicated that the prototype compound 7h can induce Apoptosis in MCF-7 and MDA-MB-231 cells.

Keywords

3H-quinazolin-4-one; Anti-cancer; Cytotoxic agents; trans-stilbene.

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