Literature

Abstract

The enantiomers of cis-(+/-)-methyl (1R,2S/1S,2R)-2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-1-(4-methylphenyl)cyclopropanecarboxylate [1, (+/-)-PPCC], a selective sigma ligand, were synthesized. The (+)- and (-)-enantiomers bind predominantly to sigma(1) receptors and have a reduced sigma(2) affinity. Both individually restore the astroglial oxidative status modified by glutamate, counteracting also transglutaminase-2 overexpression. They exhibited in vivo anti-opioid effects on kappa opioid (KOP) receptor-mediated analgesia. Our findings demonstrate that the enantiomers display mainly sigma(1) agonist activity and that they have neuroprotective effects.

DOI： 10.1021/jm100116p

Synthesis and Resolution ofcis-(±)-Methyl (1R,2S/1S,2R)-2-[(4-Hydroxy-4-phenylpiperidin-1-yl)methyl]-1-(4-methylphenyl)cyclopropanecarboxylate [(±)-PPCC)]: New σ Receptor Ligands with Neuroprotective Effect

Journal of Medicinal Chemistry 2010.0

(+)-Methyl (1R,2S)-2-{[4-(4-Chlorophenyl)-4-hydroxypiperidin-1-yl]methyl}-1-phenylcyclopropanecarboxylate [(+)-MR200] Derivatives as Potent and Selective Sigma Receptor Ligands: Stereochemistry and Pharmacological Properties

Journal of Medicinal Chemistry 2018.0

Novel Sigma Receptor Ligands: Synthesis and Biological Profile

Journal of Medicinal Chemistry 2007.0

Synthesis and preliminary pharmacological evaluation of the four stereoisomers of (2S)-2-(2′-phosphono-3′-phenylcyclopropyl)glycine, the first class of 3′-substituted transC1′−2′-2-(2′-phosphonocyclopropyl)glycines

Bioorganic & Medicinal Chemistry 2007.0

Novel Potent and Selective σ Ligands: Evaluation of Their Agonist and Antagonist Properties

Journal of Medicinal Chemistry 2011.0

Design and Synthesis of New Bifunctional Sigma-1 Selective Ligands with Antioxidant Activity