Toward the identification of neuroprotective agents: g-scale synthesis, pharmacokinetic evaluation and CNS distribution of (R)-RC-33, a promising SIGMA1 receptor agonist

Future Med Chem. 2016;8(3):287-95. doi: 10.4155/fmc.15.191. Epub 2016 Feb 22.

Abstract

Aim: Nowadays, there is a great interest in the therapeutic potential of sigma1 receptor ligands for treating different CNS pathologies. Our previous investigations led to identify (R)-RC-33 as a potent and selective S1R agonist.

Results: Herein, we report the gram-scale synthesis, pharmacokinetic profile and CNS distribution of (R)-RC-33 in the mouse to determine the most suitable dosage schedule for in vivo administration. For comparative purposes, the same experiments were also performed with PRE-084, the most widely used S1R agonist commonly in pharmacological experiments.

Discussion: (R)-RC-33 shows a similar pharmacokinetic profile and a better CNS distribution when compared with PRE-084.

Conclusion: (R)-RC-33 may be a promising candidate for in vivo studies in animal models of neurodegenerative diseases.

Keywords: CNS distribution; Parkinson's disease; S1R agonist; amyotrophic lateral sclerosis; multiple sclerosis; neurological disorders; pharmacokinetic profile.

MeSH terms

  • Biphenyl Compounds / chemical synthesis
  • Biphenyl Compounds / chemistry
  • Biphenyl Compounds / pharmacokinetics*
  • Biphenyl Compounds / pharmacology*
  • Central Nervous System Diseases / metabolism*
  • Central Nervous System Diseases / pathology
  • Dose-Response Relationship, Drug
  • Humans
  • Molecular Structure
  • Morpholines / chemistry
  • Morpholines / pharmacology
  • Neuroprotective Agents / chemical synthesis
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / pharmacokinetics*
  • Neuroprotective Agents / pharmacology*
  • Piperidines / chemical synthesis
  • Piperidines / chemistry
  • Piperidines / pharmacokinetics*
  • Piperidines / pharmacology*
  • Receptors, sigma / agonists*
  • Sigma-1 Receptor
  • Structure-Activity Relationship

Substances

  • 1-(3-biphenyl-4-ylbutyl)piperidine
  • Biphenyl Compounds
  • Morpholines
  • Neuroprotective Agents
  • Piperidines
  • Receptors, sigma
  • 2-(4-morpholino)ethyl-1-phenylcyclohexane-1-carboxylate