Discovery of highly potent and selective biphenylacylsulfonamide-based beta3-adrenergic receptor agonists and molecular modeling based on the solved X-ray structure of the beta2-adrenergic receptor: part 6

Bioorg Med Chem Lett. 2009 Aug 15;19(16):4679-83. doi: 10.1016/j.bmcl.2009.06.083. Epub 2009 Jun 25.

Abstract

As an extension of research, we have investigated modification of left-hand side (LHS) of biphenyl analogues containing an acylsulfonamide moiety in the development of potent and selective human beta(3)-adrenergic receptor (AR) agonists. Result of structure-activity relationships (SAR) and cassette-dosing evaluation in dogs showed that the hydroxynorephedrine analogue 16 had an excellent balance of in vitro and in vivo potency with pharmacokinetic profiles. In addition, to facilitate structure-based drug design (SBDD), we also have performed a docking study of biphenyl analogues based on the X-ray structure of the beta(2)-adrenergic receptor.

MeSH terms

  • Adrenergic Agonists / chemical synthesis
  • Adrenergic Agonists / chemistry*
  • Adrenergic Agonists / pharmacokinetics
  • Adrenergic beta-3 Receptor Agonists*
  • Animals
  • Binding Sites
  • Computer Simulation
  • Crystallography, X-Ray
  • Dogs
  • Drug Discovery
  • Humans
  • Models, Chemical
  • Receptors, Adrenergic, beta-2 / chemistry*
  • Receptors, Adrenergic, beta-3 / metabolism
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis
  • Sulfonamides / chemistry*
  • Sulfonamides / pharmacokinetics

Substances

  • Adrenergic Agonists
  • Adrenergic beta-3 Receptor Agonists
  • Receptors, Adrenergic, beta-2
  • Receptors, Adrenergic, beta-3
  • Sulfonamides