Copper-Promoted C-Se Cross-Coupling of 2-Selenohydantoins with Arylboronic Acids in an Open Flask

ACS Comb Sci. 2019 Jun 10;21(6):456-464. doi: 10.1021/acscombsci.9b00021. Epub 2019 May 9.

Abstract

The modification of Chan-Lam-Evans cross-coupling reaction for the selective Se-arylation of 2-selenohydantoins under base-free mild conditions via aryl boronic acids is described herein. This approach was used to synthesize novel 5-arylidene-3-substituted-2-(arylselanyl)-imidazoline-4-ones with high yields. The anticancer activity of the final compounds was evaluated in vitro against different cancer cells, and thus, the possibility of 5-arylidene-3-substituted-2-(arylselanyl)-imidazoline-4-ones successful application as cytotoxic agents was demonstrated.

Keywords: 2-selenohydantoins; Chan−Lam−Evans reaction; Se-arylation; boronic acids; cross-coupling; cytotoxicity; in vitro; open flask; selenoureas.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Boronic Acids / chemistry*
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Copper / chemistry*
  • Humans
  • Hydantoins / chemistry*
  • Imidazolines / chemical synthesis
  • Imidazolines / chemistry*
  • Imidazolines / pharmacology
  • Selenium Compounds / chemistry*

Substances

  • Antineoplastic Agents
  • Boronic Acids
  • Hydantoins
  • Imidazolines
  • Selenium Compounds
  • selenol
  • Copper