Literature DB >> 21788135

Structure selectivity relationship studies of 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[(4'-pyridyl)carboxamido]morphinan derivatives toward the development of the mu opioid receptor antagonists.

Yunyun Yuan1, Orgil Elbegdorj, Jianyang Chen, Shashidhar K Akubathini, Irina O Beletskaya, Dana E Selley, Yan Zhang.   

Abstract

Mu opioid receptor antagonists have been applied to target a variety of diseases clinically. The current study is designed to explore the structure selectivity relationship (SSR) of 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[(4'-pyridyl)carboxamido]morphinan (NAP), a lead compound identified as a selective mu opioid receptor antagonist based on the previous study. Among a series of NAP derivatives synthesized, compounds 6 (NMP) and 9 (NGP) maintained comparable binding affinity, selectivity and efficacy to the lead compound. Particularly, the mu opioid receptor selectivity over kappa opioid receptor of NGP was considerably enhanced compared to that of NAP. Overall, the preliminary SSR supported our original hypothesis that an alternate 'address' domain may exist in the mu opioid receptor, which favors the ligands carrying a hydrogen bond acceptor and an aromatic system to selectively recognize the mu opioid receptor. Published by Elsevier Ltd.

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Year:  2011        PMID： 21788135      PMCID： PMC3171173          DOI： 10.1016/j.bmcl.2011.06.135

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  41 in total

1.  Reinstatement of cocaine place-conditioning prevented by the peptide kappa-opioid receptor antagonist arodyn.

Authors:  A N Carey; K Borozny; J V Aldrich; J P McLaughlin
Journal:  Eur J Pharmacol       Date:  2007-05-13       Impact factor: 4.432

2.  ICI 174,864, a selective delta opioid antagonist, reverses the learning impairment produced by [leu]enkephalin.

Authors:  G Schulteis; J L Martinez
Journal:  Psychopharmacology (Berl)       Date:  1990       Impact factor: 4.530

3.  Application of the message-address concept in the design of highly potent and selective non-peptide delta opioid receptor antagonists.

Authors:  P S Portoghese; M Sultana; H Nagase; A E Takemori
Journal:  J Med Chem       Date:  1988-02       Impact factor: 7.446

4.  Naltrexone, an antagonist for the treatment of heroin dependence. Effects in man.

Authors:  W R Martin; D R Jasinski; P A Mansky
Journal:  Arch Gen Psychiatry       Date:  1973-06

5.  Mu-opioid receptor specific antagonist cyprodime: characterization by in vitro radioligand and [35S]GTPgammaS binding assays.

Authors:  A Márki; K Monory; F Otvös; G Tóth; R Krassnig; H Schmidhammer; J R Traynor; B P Roques; R Maldonado; A Borsodi
Journal:  Eur J Pharmacol       Date:  1999-10-27       Impact factor: 4.432

6.  The clinical pharmacology of naltrexone: pharmacology and pharmacodynamics.

Authors:  K Verebey
Journal:  NIDA Res Monogr       Date:  1981

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

Authors:  H Schmidhammer; W P Burkard; L Eggstein-Aeppli; C F Smith
Journal:  J Med Chem       Date:  1989-02       Impact factor: 7.446

8.  Antidepressant-like effects of kappa-opioid receptor antagonists in the forced swim test in rats.

Authors:  Stephen D Mague; Andrea M Pliakas; Mark S Todtenkopf; Hilarie C Tomasiewicz; Yan Zhang; William C Stevens; Robert M Jones; Philip S Portoghese; William A Carlezon
Journal:  J Pharmacol Exp Ther       Date:  2003-04       Impact factor: 4.030

Review 9.  Pharmacological mechanisms of naltrexone and acamprosate in the prevention of relapse in alcohol dependence.

Authors:  John Littleton; Walter Zieglgänsberger
Journal:  Am J Addict       Date:  2003

10.  Involvement of the kappa-opioid receptor in the anxiogenic-like effect of CP 55,940 in male rats.

Authors:  S Marín; E Marco; M Biscaia; B Fernández; M Rubio; C Guaza; H Schmidhammer; M P Viveros
Journal:  Pharmacol Biochem Behav       Date:  2003-02       Impact factor: 3.533
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  9 in total

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Authors:  Susruta Majumdar; Joan Subrath; Valerie Le Rouzic; Lisa Polikar; Maxim Burgman; Kuni Nagakura; Julie Ocampo; Nathan Haselton; Anna R Pasternak; Steven Grinnell; Ying-Xian Pan; Gavril W Pasternak
Journal:  J Med Chem       Date:  2012-07-16       Impact factor: 7.446

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

Authors:  Yunyun Yuan; Saheem A Zaidi; David L Stevens; Krista L Scoggins; Philip D Mosier; Glen E Kellogg; William L Dewey; Dana E Selley; Yan Zhang
Journal:  Bioorg Med Chem       Date:  2015-03-06       Impact factor: 3.641

3.  6β-N-heterocyclic substituted naltrexamine derivative NAP as a potential lead to develop peripheral mu opioid receptor selective antagonists.

Authors:  Yunyun Yuan; David L Stevens; Amanda Braithwaite; Krista L Scoggins; Edward J Bilsky; Hamid I Akbarali; William L Dewey; Yan Zhang
Journal:  Bioorg Med Chem Lett       Date:  2012-05-26       Impact factor: 2.823

4.  Binding mode analyses of NAP derivatives as mu opioid receptor selective ligands through docking studies and molecular dynamics simulation.

Authors:  Huiqun Wang; Saheem A Zaidi; Yan Zhang
Journal:  Bioorg Med Chem       Date:  2017-03-06       Impact factor: 3.641

5.  Novel 6β-acylaminomorphinans with analgesic activity.

Authors:  András Váradi; Sándor Hosztafi; Valerie Le Rouzic; Gergő Tóth; Ákos Urai; Béla Noszál; Gavril W Pasternak; Steven G Grinnell; Susruta Majumdar
Journal:  Eur J Med Chem       Date:  2013-09-22       Impact factor: 6.514

6.  Design, synthesis, and biological evaluation of 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[(4'-pyridyl)carboxamido]morphinan derivatives as peripheral selective μ opioid receptor Agents.

Authors:  Yunyun Yuan; Orgil Elbegdorj; Jianyang Chen; Shashidhar K Akubathini; Feng Zhang; David L Stevens; Irina O Beletskaya; Krista L Scoggins; Zhenxian Zhang; Phillip M Gerk; Dana E Selley; Hamid I Akbarali; William L Dewey; Yan Zhang
Journal:  J Med Chem       Date:  2012-11-09       Impact factor: 7.446

7.  Opioid receptor selectivity profile change via isosterism for 14-O-substituted naltrexone derivatives.

Authors:  Yan Zhang; Orgil Elbegdorj; Yunyun Yuan; Irina O Beletskaya; Dana E Selley
Journal:  Bioorg Med Chem Lett       Date:  2013-05-16       Impact factor: 2.823

8.  Verifying the role of 3-hydroxy of 17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-6β-[(4'-pyridyl) carboxamido]morphinan derivatives via their binding affinity and selectivity profiles on opioid receptors.

Authors:  Boshi Huang; Rama Gunta; Huiqun Wang; Mengchu Li; Danni Cao; Rolando E Mendez; James C Gillespie; Chongguang Chen; Lan-Hsuan M Huang; Lee-Yuan Liu-Chen; Dana E Selley; Yan Zhang
Journal:  Bioorg Chem       Date:  2021-02-09       Impact factor: 5.275

9.  Exploring naltrexamine derivatives featuring azaindole moiety via nitrogen-walk approach to investigate their in vitro pharmacological profiles at the mu opioid receptor.

Authors:  Hongguang Ma; Huiqun Wang; James C Gillespie; Rolando E Mendez; Dana E Selley; Yan Zhang
Journal:  Bioorg Med Chem Lett       Date:  2021-03-22       Impact factor: 2.940
  9 in total

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