Literature DB >> 17962026

The influence of esters and carboxylic acids as the N-substituent of opioids. Part 1: Benzomorphans.

Matthew D Metcalf1, Mario D Aceto, Louis S Harris, James H Woods, John R Traynor, Andrew Coop, Everette L May.   

Abstract

To investigate the effects of carboxylic ester and acid moieties as the N-substituent of opioids, a short series of racemic N-substituted normetazocines was prepared. The introduction of both groups as the normetazocine N-substituent produced compounds which displayed low potency in vitro and in vivo, with the esters displaying the greater activity. The pharmacology of the compounds is discussed with implications resulting from potential in vivo metabolic hydrolysis.

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Year:  2007        PMID: 17962026      PMCID: PMC2254757          DOI: 10.1016/j.bmc.2007.10.030

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  10 in total

1.  N-(trifluoromethyl)benzyl substituted N-normetazocines and N-norketobemidones.

Authors:  Everette L May; Andrew Coop; James H Woods; Mario D Aceto; Edward R Bowman; Louis S Harris; John R Traynor
Journal:  Bioorg Med Chem       Date:  2003-01-02       Impact factor: 3.641

Review 2.  2002 Medicinal Chemistry Division Award address: monoamine transporters and opioid receptors. Targets for addiction therapy.

Authors:  F Ivy Carroll
Journal:  J Med Chem       Date:  2003-05-08       Impact factor: 7.446

3.  Brief history of the Drug Evaluation Committee (DEC) and its role in the college on problems of drug dependence.

Authors:  S Stevens Negus
Journal:  Drug Alcohol Depend       Date:  2006-04-28       Impact factor: 4.492

4.  Synthesis and in vitro and in vivo activity of (-)-(1R,5R,9R)- and (+)-(1S,5S,9S)-N-alkenyl-, -N-alkynyl-, and -N-cyanoalkyl-5, 9-dimethyl-2'-hydroxy-6,7-benzomorphan homologues.

Authors:  E L May; A E Jacobson; M V Mattson; J R Traynor; J H Woods; L S Harris; E R Bowman; M D Aceto
Journal:  J Med Chem       Date:  2000-12-28       Impact factor: 7.446

Review 5.  Predictive value of analgesic assays in mice and rats.

Authors:  R I Taber
Journal:  Adv Biochem Psychopharmacol       Date:  1973

6.  Inhibition of writhing by narcotic antagonists.

Authors:  J Pearl; L S Harris
Journal:  J Pharmacol Exp Ther       Date:  1966-11       Impact factor: 4.030

7.  New approaches to the evaluation of opioid agonists and antagonists upon the isolated, electrically stimulated mouse vas deferens preparation.

Authors:  C B Smith
Journal:  NIDA Res Monogr       Date:  1987

8.  N-substituted 4beta-methyl-5-(3-hydroxyphenyl)-7alpha-amidomorphans are potent, selective kappa opioid receptor antagonists.

Authors:  F Ivy Carroll; Matt S Melvin; Michel C Nuckols; S Wayne Mascarella; Hernán A Navarro; James B Thomas
Journal:  J Med Chem       Date:  2006-03-09       Impact factor: 7.446

9.  Synthesis of some pentazocine metabolites and related compounds.

Authors:  N F Albertson; F C McKay
Journal:  J Med Chem       Date:  1977-04       Impact factor: 7.446

10.  Design, synthesis, and pharmacological evaluation of ultrashort- to long-acting opioid analgetics.

Authors:  P L Feldman; M K James; M F Brackeen; J M Bilotta; S V Schuster; A P Lahey; M W Lutz; M R Johnson; H J Leighton
Journal:  J Med Chem       Date:  1991-07       Impact factor: 7.446

  10 in total
  2 in total

1.  Synthesis and Structure-Activity Relationships of (-)-cis-N-Normetazocine-Based LP1 Derivatives.

Authors:  Lorella Pasquinucci; Carmela Parenti; Emanuele Amata; Zafiroula Georgoussi; Paschalina Pallaki; Valeria Camarda; Girolamo Calò; Emanuela Arena; Lucia Montenegro; Rita Turnaturi
Journal:  Pharmaceuticals (Basel)       Date:  2018-05-05

2.  Synthesis and Structure-Activity Relationships of LP1 Derivatives: N-Methyl-N-phenylethylamino Analogues as Novel MOR Agonists.

Authors:  Rita Turnaturi; Carmela Parenti; Orazio Prezzavento; Agostino Marrazzo; Paschalina Pallaki; Zafiroula Georgoussi; Emanuele Amata; Lorella Pasquinucci
Journal:  Molecules       Date:  2018-03-16       Impact factor: 4.411

  2 in total

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