Syntheses and biological activities of sulfoximine-based acyclic triaryl olefins

Bioorg Med Chem Lett. 2012 Jul 1;22(13):4307-9. doi: 10.1016/j.bmcl.2012.05.018. Epub 2012 May 11.

Abstract

Sulfoximine-based acyclic triaryl olefins 8 and 9 have been prepared and initial studies have been performed to determine their biological profiles. In contrast to their sulfonyl-substituted analog 2 sulfoximines 8 and 9 show low COX inhibitory activity. All compounds affect the estrogen receptors. While sulfone 2 interacts exclusively with ER β, sulfoximines 8 and 9 reveal almost equal blocking potencies for both estrogen receptors, ER α and ER β. In the tested series, triaryl olefin 9a shows the highest inhibitory activities with 91% and 80%, respectively (at 10 μM).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis
  • Alkenes / chemistry*
  • Alkenes / pharmacology
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Cyclooxygenase 1 / chemistry
  • Cyclooxygenase 1 / metabolism
  • Cyclooxygenase 2 / chemistry
  • Cyclooxygenase 2 / metabolism
  • Cyclooxygenase Inhibitors / chemical synthesis*
  • Cyclooxygenase Inhibitors / chemistry
  • Cyclooxygenase Inhibitors / pharmacology
  • Estrogen Receptor alpha / antagonists & inhibitors
  • Estrogen Receptor alpha / metabolism
  • Estrogen Receptor beta / antagonists & inhibitors
  • Estrogen Receptor beta / metabolism
  • Humans
  • Imines / chemistry*
  • Protein Binding / drug effects
  • Sulfones / chemistry

Substances

  • Alkenes
  • Anti-Inflammatory Agents, Non-Steroidal
  • Cyclooxygenase Inhibitors
  • Estrogen Receptor alpha
  • Estrogen Receptor beta
  • Imines
  • Sulfones
  • Cyclooxygenase 1
  • Cyclooxygenase 2