New synthesis of tic-hydantoins sigma-1 ligands and pharmacological evaluation on cocaine-induced stimulant effects

Med Chem. 2010 Nov;6(6):355-73. doi: 10.2174/157340610793563956.

Abstract

Activation of the newly identified σ₁ chaperone protein is involved in several aspects of the psychostimulant and addictive effects of cocaine. The development of ligands that selectively target the σ₁ protein may lead to putative potent anti-cocaine agents. We report here a new and more convergent synthetic pathway to amino side chain substituted hydantoins. Twenty new analogs of our lead compound were synthesized. None of them showed better in vitro affinity for σ₁ receptor than our lead compound. Nevertheless, three of them, obtained as racemates, showed high in vitro affinity and selectivity for σ₁ receptor. A preliminary in vivo evaluation of their pharmacological activity identified compound 22 as one that increases cocaine-induced locomotor stimulation and therefore acts as a potential efficient σ₁ agonist.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Central Nervous System Stimulants / pharmacology*
  • Cocaine / pharmacology*
  • Humans
  • Hydantoins / chemical synthesis
  • Hydantoins / chemistry*
  • Hydantoins / pharmacology
  • Ligands
  • Motor Activity
  • Receptors, sigma / agonists*
  • Receptors, sigma / antagonists & inhibitors
  • Receptors, sigma / metabolism
  • Sigma-1 Receptor

Substances

  • Central Nervous System Stimulants
  • Hydantoins
  • Ligands
  • Receptors, sigma
  • Cocaine