Literature DB >> 17601735

Functionalization of the 6,14-bridge of the orvinols. Part 3: preparation and pharmacological evaluation of 18- and 19-hydroxyl substituted orvinols.

Huifang Wu1, Trudy A Smith, Hongyan Huang, Jia Bei Wang, Jeffrey R Deschamps, Andrew Coop.   

Abstract

The orvinols are a class of potent opioids which have been extensively studied, yet little is known about the effects of introducing substituents into the 18- and 19-positions. The etheno bridge of thevinone was hydroxylated to give both the 18- and 19-hydroxyl substituted thevinols. After 3-O-demethylation to the corresponding orvinols, binding and GTPgammaS functional assays indicated that hydroxyl substitution at the 18- and 19-positions differentially affects the mu opioid efficacy of orvinols.

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Year:  2007        PMID: 17601735      PMCID: PMC2084076          DOI: 10.1016/j.bmcl.2007.06.050

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


  9 in total

Review 1.  Major increases in opioid analgesic abuse in the United States: concerns and strategies.

Authors:  Wilson M Compton; Nora D Volkow
Journal:  Drug Alcohol Depend       Date:  2005-07-14       Impact factor: 4.492

2.  Thienorphine: receptor binding and behavioral effects in rhesus monkeys.

Authors:  Jun-Xu Li; Ginger L Becker; John R Traynor; Ze-Hui Gong; Charles P France
Journal:  J Pharmacol Exp Ther       Date:  2007-01-12       Impact factor: 4.030

Review 3.  Medications development: successes and challenges.

Authors:  Frank Vocci; Walter Ling
Journal:  Pharmacol Ther       Date:  2005-10       Impact factor: 12.310

4.  Selected cysteine residues in transmembrane domains of mu-opioid receptor are critical for effects of sulfhydryl reagents.

Authors:  H B Deng; W Guang; J B Wang
Journal:  J Pharmacol Exp Ther       Date:  2000-04       Impact factor: 4.030

5.  Pharmacokinetics, bioavailability and opioid effects of liquid versus tablet buprenorphine.

Authors:  Peggy Compton; Walter Ling; David Moody; Nora Chiang
Journal:  Drug Alcohol Depend       Date:  2005-09-06       Impact factor: 4.492

6.  Structural determinants of opioid activity in the orvinols and related structures: ethers of orvinol and isoorvinol.

Authors:  A Coop; C L Norton; I Berzetei-Gurske; J Burnside; L Toll; S M Husbands; J W Lewis
Journal:  J Med Chem       Date:  2000-05-04       Impact factor: 7.446

7.  Functionalization of the 6,14-bridge of the orvinols. 2. Preparation of 18- and 19-hydroxyl-substituted thevinols and their treatment with benzyl bromide.

Authors:  Huifang Wu; Denzil Bernard; Weibin Chen; Gary D Strahan; Jeffrey R Deschamps; Damon A Parrish; John W Lewis; Alexander D MacKerell; Andrew Coop
Journal:  J Org Chem       Date:  2005-03-04       Impact factor: 4.354

8.  Role of mPKCI, a novel mu-opioid receptor interactive protein, in receptor desensitization, phosphorylation, and morphine-induced analgesia.

Authors:  Wei Guang; Hongyan Wang; Tao Su; I Bernard Weinstein; Jia Bei Wang
Journal:  Mol Pharmacol       Date:  2004-11       Impact factor: 4.436

Review 9.  The orvinols and related opioids--high affinity ligands with diverse efficacy profiles.

Authors:  John W Lewis; Stephen M Husbands
Journal:  Curr Pharm Des       Date:  2004       Impact factor: 3.116

  9 in total
  1 in total

Review 1.  Diels-Alder Adducts of Morphinan-6,8-Dienes and Their Transformations.

Authors:  János Marton; Anikó Fekete; Paul Cumming; Sándor Hosztafi; Pál Mikecz; Gjermund Henriksen
Journal:  Molecules       Date:  2022-04-30       Impact factor: 4.927

  1 in total

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