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
-
Are Selenoproteins Important for the Cancer Protective Effects of Selenium?
Current Nutrition & Food Science Recent Developments of the PET Imaging Agents for Metabotropic Glutamate Receptor Subtype 5
Current Topics in Medicinal Chemistry Could Better Phenotyping Small Vessel Disease Provide New Insights into Alzheimer Disease and Improve Clinical Trial Outcomes?
Current Alzheimer Research Experimental Drugs for Neuropathic Pain
Current Neuropharmacology Convection Enhanced Delivery of Macromolecules for Brain Tumors
Current Drug Discovery Technologies P2X7 Receptor-Associated Programmed Cell Death in the Pathophysiology of Hemorrhagic Stroke
Current Neuropharmacology Melatonin Effects in REM Sleep Behavior Disorder Associated with Obstructive Sleep Apnea Syndrome: A Case Series
Current Alzheimer Research Perinatal and Neonatal Outcomes of Lithium-Treated and Untreated Bipolar Women During Pregnancy: A Review of Present Literature
Current Psychopharmacology Survey of Recent Literature Related to the Biologically Active 4(3H)-Quinazolinones Containing Fused Heterocycles
Current Medicinal Chemistry Current Overview of Inorganic Nanoparticles for the Treatment of Central Nervous System (CNS) Diseases
Current Nanomaterials Current & Future Therapies of Erectile Dysfunction in Neurological Disorders
Recent Patents on CNS Drug Discovery (Discontinued) The Role of Neuropeptides and Neurohormones in Neurogenic Cardiac Arrhythmias
Current Drug Targets - Cardiovascular & Hematological Disorders Neural Networks in Generalized Epilepsy and Novel Antiepileptic Drugs
Current Pharmaceutical Design Physiopathological Roles of P2X Receptors in the Central Nervous System
Current Medicinal Chemistry Insights into the Role of mTOR/AMPK as a Potential Target for Anticancer Therapy
Current Drug Therapy Selenium in the Therapy of Neurological Diseases. Where is it Going?
Current Neuropharmacology Rational Understanding of Nicotinic Receptors Drug Binding
Current Topics in Medicinal Chemistry Drug Repositioning for Treatment of Movement Disorders: From Serendipity to Rational Discovery Strategies
Current Topics in Medicinal Chemistry Functional Food with Some Health Benefits, So Called Superfood: A Review
Current Nutrition & Food Science Synthesis and First Evaluation of [<sup>18</sup>F]Fluorocyano- and [<sup>18</sup>F]Fluoronitroquinoxalinedione as Putative AMPA Receptor Antagonists
Medicinal Chemistry