Synthesis of new opioid derivatives with a propellane skeleton and their pharmacology: Part 1
The observation that 17-cyclopropylmethylmorphinan derivatives without the 4,5-epoxy ring showed more κ selectivity than those with a 4,5-epoxy ring led us to develop a working hypothesis: the position of the plane composed of the A and B rings would influence the opioid receptor type selectivity an...
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Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2011-07, Vol.21 (13), p.4104-4107 |
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creator | Yamamoto, Naoshi Fujii, Hideaki Nemoto, Toru Nakajima, Ryo Momen, Shinobu Izumimoto, Naoki Hasebe, Ko Mochizuki, Hidenori Nagase, Hiroshi |
description | The observation that 17-cyclopropylmethylmorphinan derivatives without the 4,5-epoxy ring showed more κ selectivity than those with a 4,5-epoxy ring led us to develop a working hypothesis: the position of the plane composed of the A and B rings would influence the opioid receptor type selectivity and that the decrease in the torsion angle C11–C12–C13–C14 could improve the κ selectivity. Consistent with our hypothesis, KNT-42 with an N-cyclopropylmethyl propellane structure, whose A and B rings were fixed in a torsion angle of approximately 0°, showed κ selective agonist activity. |
doi_str_mv | 10.1016/j.bmcl.2011.04.147 |
format | Article |
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Consistent with our hypothesis, KNT-42 with an N-cyclopropylmethyl propellane structure, whose A and B rings were fixed in a torsion angle of approximately 0°, showed κ selective agonist activity.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2011.04.147</identifier><identifier>PMID: 21641798</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>agonists ; Analgesics ; Analgesics, Opioid - chemical synthesis ; Analgesics, Opioid - chemistry ; Analgesics, Opioid - pharmacology ; Animals ; Biological and medical sciences ; Bridged-Ring Compounds - chemical synthesis ; Bridged-Ring Compounds - chemistry ; Bridged-Ring Compounds - pharmacology ; Cells, Cultured ; chemical derivatives ; Medical sciences ; Mice ; Molecular Structure ; Neuropharmacology ; pharmacology ; Pharmacology. Drug treatments ; Protein Binding - drug effects ; Receptors, Opioid, kappa - metabolism ; Structure-Activity Relationship ; Substrate Specificity ; synthesis</subject><ispartof>Bioorganic & medicinal chemistry letters, 2011-07, Vol.21 (13), p.4104-4107</ispartof><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier Ltd. 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Consistent with our hypothesis, KNT-42 with an N-cyclopropylmethyl propellane structure, whose A and B rings were fixed in a torsion angle of approximately 0°, showed κ selective agonist activity.</description><subject>agonists</subject><subject>Analgesics</subject><subject>Analgesics, Opioid - chemical synthesis</subject><subject>Analgesics, Opioid - chemistry</subject><subject>Analgesics, Opioid - pharmacology</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Bridged-Ring Compounds - chemical synthesis</subject><subject>Bridged-Ring Compounds - chemistry</subject><subject>Bridged-Ring Compounds - pharmacology</subject><subject>Cells, Cultured</subject><subject>chemical derivatives</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>Neuropharmacology</subject><subject>pharmacology</subject><subject>Pharmacology. 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subjects | agonists Analgesics Analgesics, Opioid - chemical synthesis Analgesics, Opioid - chemistry Analgesics, Opioid - pharmacology Animals Biological and medical sciences Bridged-Ring Compounds - chemical synthesis Bridged-Ring Compounds - chemistry Bridged-Ring Compounds - pharmacology Cells, Cultured chemical derivatives Medical sciences Mice Molecular Structure Neuropharmacology pharmacology Pharmacology. Drug treatments Protein Binding - drug effects Receptors, Opioid, kappa - metabolism Structure-Activity Relationship Substrate Specificity synthesis |
title | Synthesis of new opioid derivatives with a propellane skeleton and their pharmacology: Part 1 |
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