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

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.

Organofluorine Isoselenocyanate Analogues of Sulforaphane: Synthesis and Anticancer Activity

“…The cytotoxic nonselective therapeutics, such as doxorubicin or paclitaxel, must be administered but these are associated with severe adverse effects. The literature data on the selectivity of doxorubicin, tamoxifen, and paclitaxel in breast cancer cell lines reports SI values lower than 2 . In this respect, the newly synthesized sulforaphane analogues containing both fluorine and selenium atoms, particularly sulfoxide 8 i , which exhibited the highest selectivity toward the triple‐negative MDA‐MB‐231 breast cancer cell line, may be considered as promising candidates for breast cancer therapy.…”

Antibacterial and Antitubercular Activities of Cinnamylideneacetophenones

“…Synthesis of cinnamylideneacetophenones 2 – 18 was achieved by Claisen-Schmidt condensation, using protocol reported by Weldon and co-authors, with minor modifications [ 20 , 21 , 22 ] ( Scheme 2 ).…”

“…The structure of compounds was identified by their melting point, UV-Vis, 1 H-NMR, and 13 C-NMR spectra analyses and was compared with previous data [ 20 , 21 , 22 , 23 ]. Out of 17 compounds, compound 9 was identified as a new chemical entity.…”

“…All starting reagents were purchased from Sigma-Aldrich. Compounds were synthesized by Claisen-Schmidt condensation, according to the method reported by Weldon and co-authors, with minor modifications [ 20 , 21 , 22 ]. Cinnamaldehyde (6 mmol) was added to solution of respective acetophenone (5 mmol) in ethanol (5 mL).…”

Potassium Carbonate Assisted Synthesis Of α, β, γ, δ-Unsaturated Ketones

“…The synthetic applications of cinnamaldehyde are vast and related to its abundance and low economic costs and have led to a collection of compounds with high chemodiversity [2]. The Cinnamylideneacetophenones derivative is α, β, γ, δ -unsaturated ketones show important bioactivities like antibacterial and antitubercular [3], antinociceptive [4], cytotoxicity in breast cancer cell [5], the antiproliferative effect [6], an antileshmanial activity [7], inhibitors of protein kinase C [8], antifungal [9], antimalarial [10] and antioxidant activity [11]. The cinnamylidene ketones have optimistic non liner optical material, in particular, in the short wavelength region [12].…”