An efficient asymmetric synthesis of the potent beta-blocker ICI-118,551 allows the determination of enantiomer dependency on biological activity

Chem Commun (Camb). 2010 Jun 14;46(22):3953-4. doi: 10.1039/c0cc00142b. Epub 2010 Apr 30.

Abstract

A highly efficient, practical and flexible two-step asymmetric synthesis of the beta(2)-selective beta-blocker ICI 118,551 is reported, allowing an unambiguous determination of the dependency of biological activity with optical activity, revealing the S,S-enantiomer to be the most potent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adrenergic beta-1 Receptor Antagonists
  • Adrenergic beta-2 Receptor Antagonists
  • Adrenergic beta-Antagonists / chemical synthesis*
  • Adrenergic beta-Antagonists / chemistry
  • Crystallography, X-Ray
  • Molecular Conformation
  • Propanolamines / chemical synthesis*
  • Propanolamines / chemistry
  • Receptors, Adrenergic, beta-1 / metabolism
  • Receptors, Adrenergic, beta-2 / metabolism
  • Stereoisomerism

Substances

  • Adrenergic beta-1 Receptor Antagonists
  • Adrenergic beta-2 Receptor Antagonists
  • Adrenergic beta-Antagonists
  • Propanolamines
  • Receptors, Adrenergic, beta-1
  • Receptors, Adrenergic, beta-2
  • ICI 118551