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Bioorg Med Chem Lett. 2014 Aug 1;24(15):3381-4. doi: 10.1016/j.bmcl.2014.05.089. Epub 2014 Jun 4.

One-pot synthesis of cinnamylideneacetophenones and their in vitro cytotoxicity in breast cancer cells.

Author information

1
Department of Pharmaceutical and Administrative Sciences, School of Pharmacy, Loma Linda University, Loma Linda, CA, United States.
2
Department of Pharmaceutical Sciences, Hampton University, Hampton, VA, United States.
3
Department of Basic Sciences, School of Medicine, Loma Linda University, Loma Linda, CA, United States.
4
Department of Basic Sciences, School of Medicine, Loma Linda University, Loma Linda, CA, United States; Department of Chemistry, Geology and Physics, School of Mathematics, Science & Technology, Elizabeth City State University, Elizabeth City, NC, United States.
5
Department of Pharmaceutical and Administrative Sciences, School of Pharmacy, Loma Linda University, Loma Linda, CA, United States; Department of Basic Sciences, School of Medicine, Loma Linda University, Loma Linda, CA, United States.
6
Department of Neuroscience and Pharmacology, Meharry Medical College, Nashville, TN, United States.
7
Department of Pharmaceutical and Administrative Sciences, School of Pharmacy, Loma Linda University, Loma Linda, CA, United States; Department of Basic Sciences, School of Medicine, Loma Linda University, Loma Linda, CA, United States; Department of Chemistry, University of California, Riverside, CA 92521, United States. Electronic address: ebrantley@llu.edu.

Abstract

A series of cinnamylideneacetophenones were synthesized via a modified Claisen-Schmidt condensation reaction and evaluated for cytotoxicity against breast cancer cells using the Alamar Blue™ assay. Derivatives 17 and 18 bearing a 2-nitro group on the B ring, exhibited sub-micromolar cytotoxicity in MCF-7 cells (IC50=71 and 1.9 nM), respectively. Derivative 17 also displayed sub-micromolar (IC50=780 nM) cytotoxicity in MDA-MB-468 cells. Additionally, 17 and 18 displayed significantly less cytotoxicity than the chemotherapeutic doxorubicin in non-tumorigenic MCF-10A cells. This study provides evidence supporting the continued development of nitro-substituted cinnamylideneacetophenones as small molecules to treat breast cancer.

KEYWORDS:

Breast cancer; Chalcone derivatives; Cytotoxicity; Estrogen receptor; Leinamycin

PMID:
24957352
PMCID:
PMC4145842
DOI:
10.1016/j.bmcl.2014.05.089
[Indexed for MEDLINE]
Free PMC Article

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