(E)-β-Trifluoromethyl vinylsulfones as antitumor agents: Synthesis and biological evaluations

Eur J Med Chem. 2022 Mar 15:232:114197. doi: 10.1016/j.ejmech.2022.114197. Epub 2022 Feb 14.

Abstract

A three-component reaction of phenylactylene, trifluoromethyl thianthrenium triflate (TT-CF3+OTf-) and sodium sulfinates under extremely mild conditions is developed, leading to various trifluoromethyl-substituted vinyl sulfones in moderate to good yields with excellent stereoselectivity. Additionally, elaboration of trifluoromethyl-substituted vinyl sulfone by palladium-catalyzed amination is performed. These trifluoromethyl-substituted vinyl sulfones are further evaluated for several assays against different tumor cells and the antitumor mechanism in cytotoxic autophagy induced by PI3K/Akt/mTOR signal is investigated.

Keywords: Antitumor; Cytotoxic autophagy; PI3K/Akt/mTOR; Trifluoromethylation; Vinyl sulfones.

MeSH terms

  • Antineoplastic Agents* / pharmacology
  • Catalysis
  • Molecular Structure
  • Palladium
  • Phosphatidylinositol 3-Kinases*

Substances

  • Antineoplastic Agents
  • Palladium