Natural-Antioxidant-Inspired Benzo[b]selenophenes: Synthesis, Redox Properties, and Antiproliferative Activity

Chem Asian J. 2016 Jul 5;11(13):1929-38. doi: 10.1002/asia.201600472. Epub 2016 Jun 7.

Abstract

The cyclization of arylalkynes under selenobromination conditions, combined with an acid-induced 3,2-aryl shift, was elaborated as a general synthetic pathway for the preparation of polyhydroxy-2- and -3-arylbenzo[b]selenophenes from the same starting materials. The redox properties, free-radical-scavenging ability, and cytotoxicity against malignant cell lines (MCF-7, MDA-MB-231, HepG2, and 4T1) of the synthesized compounds were explored, and the obtained results were used to consider the structure-activity relationships (SARs) in these compounds. Consequently, the structural features that were responsible for the highly potent peroxyl-radical-scavenging activity were established.

Keywords: antiproliferative activity; cytotoxicity; radicals; redox chemistry; selenophenes.

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry*
  • Antioxidants / pharmacology*
  • Benzene Derivatives / chemical synthesis
  • Benzene Derivatives / chemistry
  • Benzene Derivatives / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cyclization
  • Humans
  • Neoplasms / drug therapy
  • Organoselenium Compounds / chemical synthesis
  • Organoselenium Compounds / chemistry*
  • Organoselenium Compounds / pharmacology*
  • Oxidation-Reduction / drug effects

Substances

  • Antineoplastic Agents
  • Antioxidants
  • Benzene Derivatives
  • Organoselenium Compounds