Abstract
(±)-Trans-Ph/Et and (±)-cis-Ph/Et 1-(2-ethyl-1-phenylcyclohexyl)piperidine were synthesized from 2-ethylcyclohexanone. In contrast to the corresponding trans-substituted 2-methyl compound which is 5x more potent than PCP, the trans-2-ethyl derivative has a 75x lower affinity for the PCP binding site. The cis-2-ethyl isomer is inactive like the cis-2-methyl derivative. (±)-1-(1- Phenylcyclohexyl)-2-methylpiperidine is almost as active as the parent PCP. Reduction of the aromatic ring or quaternization of the piperidine in PCP reduces the affinity for the PCP site.
Keywords: Phencyclidine, Conformations, NMDA receptor, PCP binding site, Bruylants reaction, Ritter reaction
Letters in Drug Design & Discovery
Title: Synthesis and Preliminary Biochemical Evaluation of Novel Derivatives of PCP
Volume: 7 Issue: 2
Author(s): Joannes T.M. Linders, David C. Furlano, Mariena V. Mattson, Arthur E. Jacobson and Kenner C. Rice
Affiliation:
Keywords: Phencyclidine, Conformations, NMDA receptor, PCP binding site, Bruylants reaction, Ritter reaction
Abstract: (±)-Trans-Ph/Et and (±)-cis-Ph/Et 1-(2-ethyl-1-phenylcyclohexyl)piperidine were synthesized from 2-ethylcyclohexanone. In contrast to the corresponding trans-substituted 2-methyl compound which is 5x more potent than PCP, the trans-2-ethyl derivative has a 75x lower affinity for the PCP binding site. The cis-2-ethyl isomer is inactive like the cis-2-methyl derivative. (±)-1-(1- Phenylcyclohexyl)-2-methylpiperidine is almost as active as the parent PCP. Reduction of the aromatic ring or quaternization of the piperidine in PCP reduces the affinity for the PCP site.
Export Options
About this article
Cite this article as:
Linders T.M. Joannes, Furlano C. David, Mattson V. Mariena, Jacobson E. Arthur and Rice C. Kenner, Synthesis and Preliminary Biochemical Evaluation of Novel Derivatives of PCP, Letters in Drug Design & Discovery 2010; 7 (2) . https://dx.doi.org/10.2174/157018010790225813
DOI https://dx.doi.org/10.2174/157018010790225813 |
Print ISSN 1570-1808 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-628X |
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
Related Articles
-
FoxO3a Governs Early Microglial Proliferation and Employs Mitochondrial Depolarization with Caspase 3, 8, and 9 Cleavage During Oxidant Induced Apoptosis
Current Neurovascular Research Pathogenesis of Stroke-Like Episodes in MELAS: Analysis of Neurovascular Cellular Mechanisms
Current Neurovascular Research Altered Homeostatic Functions in Reactive Astrocytes and Their Potential as a Therapeutic Target After Brain Ischemic Injury
Current Pharmaceutical Design Laterality of Brain Activation for Risk Factors of Addiction
Current Drug Abuse Reviews Expanding Spectrum of Sodium Potassium Chloride Co-transporters in the Pathophysiology of Diseases
Current Neuropharmacology A Focus on Microfluidics and Nanotechnology Approaches for the Ultra Sensitive Detection of MicroRNA
MicroRNA Cytochrome P450 in Neurological Disease
Current Drug Metabolism GABAergic Agonists Modulate the Glutamate Release from Frontal Cortex Synaptosomes of Rats with Experimental Autoimmune Encephalomyelitis
Inflammation & Allergy - Drug Targets (Discontinued) Antiepileptic Treatment Strategy in Vascular Malformations
Current Pharmaceutical Design Effect of Valerian Extract on GABRB3 Gene MRNA Expression and Sedation in BALB/C Mice
Current Bioactive Compounds Neural Stem Cell Niches in Health and Diseases
Current Pharmaceutical Design Structure, Pharmacology and Therapeutic Prospects of Family C G-Protein Coupled Receptors
Current Drug Targets Therapeutic Potential of Neurogenesis for Prevention and Recovery from Alzheimers Disease: Allopregnanolone as a Proof of Concept Neurogenic Agent
Current Alzheimer Research Chemistry and Biology of Thyrotropin-Releasing Hormone (TRH) and its Analogs
Current Medicinal Chemistry Aliphatic and Aromatic Oxidations, Epoxidation and S-Oxidation of Prodrugs that Yield Active Drug Metabolites
Current Medicinal Chemistry Glial Modulation of GABAergic and Glutamat ergic Neurotransmission
Current Topics in Medicinal Chemistry Mechanisms Involved in Neuroprotective Effects of Transcranial Magnetic Stimulation
CNS & Neurological Disorders - Drug Targets Fructose 1,6-Bisphosphate: A Summary of Its Cytoprotective Mechanism
Current Medicinal Chemistry Synthesis and Analysis of Anticonvulsant Activities of New 4-[2-(4- alkoxybenzylamino)ethyl]-2H-1,2,4-triazol-3(4H)-one Derivatives
Letters in Drug Design & Discovery Cyclooxygenase-2 in Synaptic Signaling
Current Pharmaceutical Design