Ultrasounds-mediated 10-seconds synthesis of chalcones as potential farnesyltransferase inhibitors. Issue 11 (1st June 2020)

• Record Type: Journal Article
• Authors: Homerin, Germain; Nica, Adrian Sorin; Farce, Amaury; Dubois, Joëlle; Ghinet, Alina
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 30:Issue 11(2020)
• Publication Date: 2020-06-01
• Subjects: Farnesyltransferase -- Inhibitor -- Chalcone -- Claisen-Schmidt -- Ultrasounds; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2020.127149
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: A broad range of chalcones and derivatives were easily and rapidly synthesized, following Claisen-Schmidt condensation of (hetero)aryl ketones and (hetero)aryl aldehydes using a ultrasound probe. A comparison was made with classical magnetic stirring experiments, and an optimization study was realized, showing lithium hydroxide to be the best basic catalyst of the studied condensations. By-products of the reactions (β-hydroxy-ketone, diketones, and cyclohexanols) were also isolated. All compounds were evaluated in vitro for their ability to inhibit human farnesyltransferase, a protein implicated in cancer and rare diseases and on the NCI-60 cancer cell lines panel. Molecules showed inhibitory activity on the target protein and cytostatic effect on different cell lines with particular activity against MCF7, breast cancer cells.