3-[3-(Piperidin-1-yl)propyl]indoles as highly selective h5-HT(1D) receptor agonists

J Med Chem. 1999 Dec 2;42(24):4981-5001. doi: 10.1021/jm9910021.

Abstract

Several 5-HT(1D/1B) receptor agonists are now entering the marketplace as treatments for migraine. This paper describes the development of selective h5-HT(1D) receptor agonists as potential antimigraine agents which may produce fewer side effects. A series of 3-[3-(piperidin-1-yl)propyl]indoles has been synthesized which has led to the identification of 80 (L-772,405), a high-affinity h5-HT(1D) receptor full agonist having 170-fold selectivity for h5-HT(1D) receptors over h5-HT(1B) receptors. L-772,405 also shows very good selectivity over a range of other serotonin and nonserotonin receptors and has excellent bioavailability following subcutaneous administration in rats. It therefore constitutes a valuable tool to delineate the role of h5-HT(1D) receptors in migraine. Molecular modeling and physical properties have been utilized to postulate the binding conformation of these compounds in the receptor cavity.

MeSH terms

  • Animals
  • Biological Availability
  • CHO Cells
  • Computer Simulation
  • Cricetinae
  • Guanosine 5'-O-(3-Thiotriphosphate) / metabolism
  • Humans
  • Indoles / chemical synthesis*
  • Indoles / metabolism
  • Indoles / pharmacokinetics
  • Male
  • Models, Molecular
  • Molecular Structure
  • Rats
  • Rats, Sprague-Dawley
  • Receptor, Serotonin, 5-HT1D
  • Receptors, Serotonin / genetics
  • Receptors, Serotonin / metabolism*
  • Recombinant Proteins / metabolism
  • Serotonin Receptor Agonists / chemical synthesis*
  • Serotonin Receptor Agonists / metabolism
  • Serotonin Receptor Agonists / pharmacokinetics
  • Structure-Activity Relationship
  • Transfection
  • Triazoles / chemical synthesis*
  • Triazoles / metabolism
  • Triazoles / pharmacokinetics

Substances

  • Indoles
  • L 772405
  • Receptor, Serotonin, 5-HT1D
  • Receptors, Serotonin
  • Recombinant Proteins
  • Serotonin Receptor Agonists
  • Triazoles
  • Guanosine 5'-O-(3-Thiotriphosphate)