Design, syntheses, and pharmacological characterization of 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(isoquinoline-3′-carboxamido)morphinan analogues as opioid receptor ligands

Bioorganic and Medicinal Chemistry

Volumn 23, Issue 8, 2015, Pages 1701-1715

  Yuan, Yunyun ^a   Zaidi, Saheem A ^a   Stevens, David L ^a   Scoggins, Krista L ^a   Mosier, Philip D ^a   Kellogg, Glen E ^a   Dewey, William L ^a   Selley, Dana E ^a   Zhang, Yan ^a  

^a VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

Antagonist; MOR; SAR; Selectivity

Indexed keywords

17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6ALPHA (1 CHLORO 4 HYDROXYISOQUINOLINE 3 CARBOXAMIDO)MORPHINAN; 17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6ALPHA (1 CHLORO 4 METHOXYISOQUINOLINE 3 CARBOXAMIDO)MORPHINAN; 17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6ALPHA (1 CHLOROISOQUINOLINE 3 CARBOXAMIDO)MORPHINAN; 17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6ALPHA (1 CYANOISOQUINOLINE 3 CARBOXAMIDO)MORPHINAN; 17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6ALPHA (1 METHYLISOQUINOLIN 3 CARBOXAMIDO)MORPHINAN; 17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6ALPHA (4 HYDROXYISOQUINOLINE 3 CARBOXAMIDO)MORPHINAN; 17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6ALPHA (4 QUINAZOLINE 2 CARBOXAMIDO)MORPHINAN; 17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6ALPHA (6 NITROISOQUINOLINE 3 CARBOXAMIDO)MORPHINAN; 17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6ALPHA (6,7 DIMETHOXYISOQUINOLINE 3 CARBOXAMIDO)MORPHINAN; 17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6ALPHA (7 DIMETHYLAMINOISOQUINOLINE 3 CARBOXAMIDO)MORPHINAN; 17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6ALPHA (7 NITROISOQUINOLINE 3 CARBOXAMIDO)MORPHINAN; 17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6ALPHA (ISOQUINOLINE 3' CARBOXAMIDO)MORPHINAN; 17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6ALPHA [(2 METHYL 1,2,3,4 TETRAHYDROISOQUINOLINE 3 CARBOXAMIDO)]MORPHINAN; 17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6ALPHA [2 (ISOQUINOLIN 3 YL)ACETAMIDO]MORPHINAN; 17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6ALPHA [2 (ISOQUINOLINE 3 CARBOXAMIDO)ACETAMIDO]MORPHINAN; 17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6ALPHA [3 (ISOQUINOLIN 3 YL)PROPANAMIDO]MORPHINAN; 17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6ALPHA(7 DIMETHYLAMINO 2 METHYL 1,2,3,4 TETRAHYDROISOQUINOLINE 3 CARBOXAMIDO)MORPHINAN; DELTA OPIATE RECEPTOR; KAPPA OPIATE RECEPTOR; MORPHINE; MORPHINE DERIVATIVE; MU OPIATE RECEPTOR; NALTREXONE; OPIATE RECEPTOR; UNCLASSIFIED DRUG; 17-CYCLOPROPYLMETHYL-3,14BETA-DIHYDROXY-4,5ALPHA-EPOXY-6ALPHA-(ISOQUINOLINE-3'-CARBOXAMIDO)MORPHINAN; ISOQUINOLINE DERIVATIVE; LIGAND; MORPHINAN DERIVATIVE; NARCOTIC ANTAGONIST;

ANALGESIC ACTIVITY; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BINDING AFFINITY; CALCIUM CELL LEVEL; COMPETITIVE BINDING ASSAY; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; MALE; MOLECULAR DYNAMICS; MOUSE; NONHUMAN; PAIN; STRUCTURE ACTIVITY RELATION; WITHDRAWAL SYNDROME; ANIMAL; ANTAGONISTS AND INHIBITORS; CHEMISTRY; CHO CELL LINE; CRICETULUS; HUMAN; METABOLISM; MORPHINE DEPENDENCE;

MUS;

ANIMALS; CHO CELLS; CRICETULUS; DRUG DESIGN; HUMANS; ISOQUINOLINES; LIGANDS; MICE; MOLECULAR DYNAMICS SIMULATION; MORPHINANS; MORPHINE DEPENDENCE; NARCOTIC ANTAGONISTS; RECEPTORS, OPIOID, MU; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84925668837     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2015.02.055     Document Type: Article

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