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. 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

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Free PMC article

One-pot Synthesis of Cinnamylideneacetophenones and Their in Vitro Cytotoxicity in Breast Cancer Cells

David J Weldon et al. Bioorg Med Chem Lett. .
Free PMC article

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.

Figures

Figure 1
Figure 1
The development of cinnamylideneacetophenones from common features of leinamycin and chalcone skeleton.
Figure 2
Figure 2
The library of cinnamylideneacetophenones synthesized for biological evaluation.
Scheme 1
Scheme 1
Synthesis of chalcone derivatives 4 and 5. (i) NaOH, H2O/EtOH (50% v/v), rt, 24 h, 74–82%.
Scheme 2
Scheme 2
Construction of target molecules 9–18. (i) NaOH, H2O/EtOH (50% v/v), rt, 24h, 65–83%.

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