Literature DB >> 19842669

14beta-Arylpropiolylamino-17-cyclopropylmethyl-7,8-dihydronormorphinones and related opioids. Further examples of pseudoirreversible mu opioid receptor antagonists.

Nick P R Nieland1, David Rennison, Jillian H Broadbear, Lauren Purington, James H Woods, John R Traynor, John W Lewis, Stephen M Husbands.   

Abstract

14beta-4'-Chlorocinnamoylaminodihydronormorphinone (2a), and analogues, are selective pseudoirreversible antagonists of the mu opioid receptor (MOR). The preparation of analogues with ethynic bonds, replacing the ethenic bond of 2a, is described. The new ligands, in mouse antinociceptive assays, had pseudoirreversible MOR antagonist activity, which, in the case of 8b was of longer duration than that of 2a. The related codeinone (9b) had only antagonist activity in vivo, in contrast to 2a's codeinone equivalent 3a, which had potent antinociceptive activity.

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Year:  2009        PMID： 19842669      PMCID： PMC2788771          DOI： 10.1021/jm901074a

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


  10 in total

Review 1.  Methoclocinnamox: a mu partial agonist with pharmacotherapeutic potential for heroin abuse.

Authors:  J H Woods; J W Lewis; G Winger; E Butelman; J Broadbear; G Zernig
Journal:  NIDA Res Monogr       Date:  1995

2.  Structural determinants of opioid activity in derivatives of 14-aminomorphinones: effect of substitution in the aromatic ring of cinnamoylaminomorphinones and codeinones.

Authors:  Nick P R Nieland; Humphrey A Moynihan; Simon Carrington; Jillian Broadbear; James H Woods; John R Traynor; Stephen M Husbands; John W Lewis
Journal:  J Med Chem       Date:  2006-08-24       Impact factor: 7.446

3.  Structural determinants of opioid activity in derivatives of 14-aminomorphinones: effects of changes to the chain linking of the C14-amino group to the aryl ring.

Authors:  David Rennison; Humphrey Moynihan; John R Traynor; John W Lewis; Stephen M Husbands
Journal:  J Med Chem       Date:  2006-10-05       Impact factor: 7.446

4.  Methocinnamox is a potent, long-lasting, and selective antagonist of morphine-mediated antinociception in the mouse: comparison with clocinnamox, beta-funaltrexamine, and beta-chlornaltrexamine.

Authors:  J H Broadbear; T L Sumpter; T F Burke; S M Husbands; J W Lewis; J H Woods; J R Traynor
Journal:  J Pharmacol Exp Ther       Date:  2000-09       Impact factor: 4.030

5.  Characterization of opiates, neuroleptics, and synthetic analogs at ORL1 and opioid receptors.

Authors:  N Zaveri; W E Polgar; C M Olsen; A B Kelson; P Grundt; J W Lewis; L Toll
Journal:  Eur J Pharmacol       Date:  2001-09-28       Impact factor: 4.432

6.  Very long-acting narcotic antagonists: the 14 beta-p-substituted cinnamoylaminomorphinones and their partial mu agonist codeinone relatives.

Authors:  M D Aceto; E R Bowman; E L May; L S Harris; J H Woods; C B Smith; F Medzihradsky; A E Jacobson
Journal:  Arzneimittelforschung       Date:  1989-05

Review 7.  Opioid ligands having delayed long-term antagonist activity: potential pharmacotherapies for opioid abuse.

Authors:  Stephen M Husbands; John W Lewis
Journal:  Mini Rev Med Chem       Date:  2003-03       Impact factor: 3.862

8.  14 beta-[(p-nitrocinnamoyl)amino]morphinones, 14 beta-[(p-nitrocinnamoyl)amino]-7,8-dihydromorphinones, and their codeinone analogues: synthesis and receptor activity.

Authors:  A Sebastian; J M Bidlack; Q Jiang; D Deecher; M Teitler; S D Glick; S Archer
Journal:  J Med Chem       Date:  1993-10-15       Impact factor: 7.446

9.  Clocinnamox: a novel, systemically-active, irreversible opioid antagonist.

Authors:  S D Comer; T F Burke; J W Lewis; J H Woods
Journal:  J Pharmacol Exp Ther       Date:  1992-09       Impact factor: 4.030

10.  Modulation by mu-opioid agonists of guanosine-5'-O-(3-[35S]thio)triphosphate binding to membranes from human neuroblastoma SH-SY5Y cells.

Authors:  J R Traynor; S R Nahorski
Journal:  Mol Pharmacol       Date:  1995-04       Impact factor: 4.436
  10 in total
  2 in total

1.  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

2.  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
  2 in total

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