Bis-vinyl selenides obtained via iron(III) catalyzed addition of PhSeSePh to alkynes: synthesis and antinociceptive activity

Org Biomol Chem. 2013 Feb 21;11(7):1199-208. doi: 10.1039/c2ob27064a.

Abstract

In the present study the synthesis and antinociceptive activity of bis-vinyl selenides, prepared via FeCl(3) promoted reaction addition of diorganyl dichalcogenides to alkynes, is described. The pharmacological results demonstrated that bis-vinyl selenides 3a, 3d, 3h and 3t elicited antinociceptive effect in the mouse formalin test. The antinociceptive effects of bis-vinyl selenides are not sensitive to electronic effects of the substituents on the aromatic ring directly bonded to the selenium atom. Bis-vinyl selenides 3h and 3t were the most promising molecules for pharmacological purposes since these bis-vinyl selenides were effective in both phases of the formalin test and against edema. A single dose of bis-vinyl selenides 3a, 3d, 3h and 3t did not cause acute toxicity in mice.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Analgesics / administration & dosage
  • Analgesics / chemistry
  • Analgesics / pharmacology*
  • Animals
  • Catalysis
  • Chlorides / chemistry*
  • Dose-Response Relationship, Drug
  • Edema / chemically induced
  • Edema / drug therapy*
  • Ferric Compounds / chemistry*
  • Formaldehyde
  • Male
  • Mice
  • Models, Molecular
  • Molecular Structure
  • Nociceptive Pain / chemically induced
  • Nociceptive Pain / drug therapy
  • Organoselenium Compounds / administration & dosage
  • Organoselenium Compounds / chemistry
  • Organoselenium Compounds / pharmacology*

Substances

  • Alkynes
  • Analgesics
  • Chlorides
  • Ferric Compounds
  • Organoselenium Compounds
  • Formaldehyde
  • ferric chloride