Literature DB >> 2536439

Synthesis and biological evaluation of 14-alkoxymorphinans. 2. (-)-N-(cyclopropylmethyl)-4,14-dimethoxymorphinan-6-one, a selective mu opioid receptor antagonist.

H Schmidhammer1, W P Burkard, L Eggstein-Aeppli, C F Smith.   

Abstract

(-)-N-(Cyclopropylmethyl)-4,14-dimethoxymorphinan-6-one (2) was synthesized with 4,14-dimethoxy-N-methylmorphinan-6-one (1) as starting material. In vivo and in vitro experiments show 2 (cyprodime) to be a pure opioid receptor antagonist. Some of these tests (opioid receptor binding assays, guinea pig ileal longitudinal muscle preparation, rat and mouse vas deferens preparation, acetic acid writhing antagonism test) indicate that 2 is a selective mu opioid receptor antagonist.

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Year:  1989        PMID： 2536439     DOI： 10.1021/jm00122a021

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  21 in total

1.  Differential effects of selective mu-, kappa- and delta-opioid antagonists on electroshock seizure threshold in mice.

Authors:  H C Jackson; D J Nutt
Journal:  Psychopharmacology (Berl)       Date:  1991       Impact factor: 4.530

2.  14-O-Heterocyclic-substituted naltrexone derivatives as non-peptide mu opioid receptor selective antagonists: design, synthesis, and biological studies.

Authors:  Guo Li; Lindsey C K Aschenbach; Hengjun He; Dana E Selley; Yan Zhang
Journal:  Bioorg Med Chem Lett       Date:  2008-12-29       Impact factor: 2.823

3.  Design, synthesis, and biological evaluation of 14-heteroaromatic-substituted naltrexone derivatives: pharmacological profile switch from mu opioid receptor selectivity to mu/kappa opioid receptor dual selectivity.

Authors:  Yunyun Yuan; Saheem A Zaidi; Orgil Elbegdorj; Lindsey C K Aschenbach; Guo Li; David L Stevens; Krista L Scoggins; William L Dewey; Dana E Selley; Yan Zhang
Journal:  J Med Chem       Date:  2013-11-07       Impact factor: 7.446

4.  Characterization of 6α- and 6β-N-heterocyclic substituted naltrexamine derivatives as novel leads to development of mu opioid receptor selective antagonists.

Authors:  Yunyun Yuan; Guo Li; Hengjun He; David L Stevens; Patrick Kozak; Krista L Scoggins; Pallabi Mitra; Phillip M Gerk; Dana E Selley; William L Dewey; Yan Zhang
Journal:  ACS Chem Neurosci       Date:  2011-05-06       Impact factor: 4.418

Review 5.  Bivalent ligands targeting chemokine receptor dimerization: molecular design and functional studies.

Authors:  Christopher Kent Arnatt; Yan Zhang
Journal:  Curr Top Med Chem       Date:  2014       Impact factor: 3.295

6.  Novel cyclic biphalin analogue with improved antinociceptive properties.

Authors:  Adriano Mollica; Alfonso Carotenuto; Ettore Novellino; Antonio Limatola; Roberto Costante; Francesco Pinnen; Azzurra Stefanucci; Stefano Pieretti; Anna Borsodi; Reza Samavati; Ferenc Zador; Sándor Benyhe; Peg Davis; Frank Porreca; Victor J Hruby
Journal:  ACS Med Chem Lett       Date:  2014-07-14       Impact factor: 4.345

7.  Binding mode characterization of 6α- and 6β-N-heterocyclic substituted naltrexamine derivatives via docking in opioid receptor crystal structures and site-directed mutagenesis studies: application of the 'message-address' concept in development of mu opioid receptor selective antagonists.

Authors:  Saheem A Zaidi; Christopher K Arnatt; Hengjun He; Dana E Selley; Philip D Mosier; Glen E Kellogg; Yan Zhang
Journal:  Bioorg Med Chem       Date:  2013-09-04       Impact factor: 3.641

8.  Design, Synthesis, and Biological Evaluation of the Third Generation 17-Cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[(4'-pyridyl)carboxamido]morphinan (NAP) Derivatives as μ/κ Opioid Receptor Dual Selective Ligands.

Authors:  Yi Zheng; Samuel Obeng; Huiqun Wang; Abdulmajeed M Jali; Bharath Peddibhotla; Dwight A Williams; Chuanchun Zou; David L Stevens; William L Dewey; Hamid I Akbarali; Dana E Selley; Yan Zhang
Journal:  J Med Chem       Date:  2019-01-11       Impact factor: 7.446

9.  Investigation of the involvement of opioid receptors in the action of anticonvulsants.

Authors:  H C Jackson; D J Nutt
Journal:  Psychopharmacology (Berl)       Date:  1993       Impact factor: 4.530

10.  Behavioral and cellular pharmacology characterization of 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(isoquinoline-3'-carboxamido)morphinan (NAQ) as a mu opioid receptor selective ligand.

Authors:  Yan Zhang; Amanda Braithwaite; Yunyun Yuan; John M Streicher; Edward J Bilsky
Journal:  Eur J Pharmacol       Date:  2014-05-08       Impact factor: 4.432
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