N-[1-(2-Phenylethyl)pyrrolidin-3-yl]-1-adamantanecarboxamides as novel 5-HT2 receptor antagonists

Bioorg Med Chem Lett. 2000 Nov 6;10(21):2457-61. doi: 10.1016/s0960-894x(00)00492-3.

Abstract

A series of 1-adamantanecarboxamides was synthesized and examined for their potency as a selective 5-HT2 receptor antagonist. We found (S)-N-[1-[2-(4-fluorophenyl)ethyl]pyrrolidin-3-yl]-1-adamantane carboxamide hydrochloride hydrate (10-(S), Y-39241) to have a high affinity and selectivity for 5-HT2 receptors, and this potent anti-platelet effect of Y-39241 was confirmed both in vitro and in vivo.

MeSH terms

  • 8-Hydroxy-2-(di-n-propylamino)tetralin / metabolism
  • Adamantane / analogs & derivatives
  • Adamantane / chemical synthesis*
  • Adamantane / chemistry
  • Adamantane / metabolism
  • Adamantane / pharmacology*
  • Animals
  • Brain Chemistry
  • Ketanserin / metabolism
  • Male
  • Molecular Structure
  • Platelet Aggregation Inhibitors / chemical synthesis
  • Platelet Aggregation Inhibitors / chemistry
  • Platelet Aggregation Inhibitors / metabolism
  • Platelet Aggregation Inhibitors / pharmacology
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / chemistry
  • Pyrrolidines / metabolism
  • Pyrrolidines / pharmacology*
  • Rabbits
  • Rats
  • Rats, Wistar
  • Receptors, Serotonin / metabolism*
  • Receptors, Serotonin, 5-HT1
  • Serotonin Antagonists / chemical synthesis*
  • Serotonin Antagonists / chemistry
  • Serotonin Antagonists / metabolism
  • Serotonin Antagonists / pharmacology*

Substances

  • N-(1-(2-(4-fluorophenyl)ethyl)pyrrolidin-3-yl)-1-adamantane carboxamide
  • Platelet Aggregation Inhibitors
  • Pyrrolidines
  • Receptors, Serotonin
  • Receptors, Serotonin, 5-HT1
  • Serotonin Antagonists
  • 8-Hydroxy-2-(di-n-propylamino)tetralin
  • Ketanserin
  • Adamantane