Literature DB >> 16942039

Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. 4. Opioid receptor binding properties of 8-[N-(4'-phenyl)-phenethyl)carboxamido] analogues of cyclazocine and ethylketocycalzocine.

Mark P Wentland1, Melissa VanAlstine, Robert Kucejko, Rongliang Lou, Dana J Cohen, Amy L Parkhill, Jean M Bidlack.   

Abstract

The synthesis and evaluation of a series of aryl-containing N-monosubstituted analogues of the lead compound 8-carboxamidocyclazocine were performed to probe a putative hydrophobic binding pocket of opioid receptors. High binding affinity to mu, kappa, and delta opioid receptors was observed for the 8-[N-(4'-phenyl)-phenethyl)carboxamido] analogue.

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Year:  2006        PMID: 16942039     DOI: 10.1021/jm060278n

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


  11 in total

Review 1.  Endogenous opiates and behavior: 2006.

Authors:  Richard J Bodnar
Journal:  Peptides       Date:  2007-09-11       Impact factor: 3.750

2.  Synthesis and pharmacological evaluation of hydrophobic esters and ethers of butorphanol at opioid receptors.

Authors:  Brian S Fulton; Brian I Knapp; Jean M Bidlack; John L Neumeyer
Journal:  Bioorg Med Chem Lett       Date:  2008-07-17       Impact factor: 2.823

3.  Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 9: Synthesis, characterization and molecular modeling of pyridinyl isosteres of N-BPE-8-CAC (1), a high affinity ligand for opioid receptors.

Authors:  Melissa A VanAlstine; Mark P Wentland; Juan Alvarez; Qing Cao; Dana J Cohen; Brian I Knapp; Jean M Bidlack
Journal:  Bioorg Med Chem Lett       Date:  2013-02-08       Impact factor: 2.823

4.  Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 8. High affinity ligands for opioid receptors in the picomolar Ki range: oxygenated N-(2-[1,1'-biphenyl]-4-ylethyl) analogues of 8-CAC.

Authors:  Mark P Wentland; Sunjin Jo; Joseph M Gargano; Melissa A VanAlstine; Dana J Cohen; Jean M Bidlack
Journal:  Bioorg Med Chem Lett       Date:  2012-10-27       Impact factor: 2.823

5.  Effect of linker substitution on the binding of butorphan univalent and bivalent ligands to opioid receptors.

Authors:  Brian S Fulton; Brian L Knapp; Jean M Bidlack; John L Neumeyer
Journal:  Bioorg Med Chem Lett       Date:  2010-01-25       Impact factor: 2.823

6.  Syntheses of novel high affinity ligands for opioid receptors.

Authors:  Mark P Wentland; Rongliang Lou; Qun Lu; Yigong Bu; Christoph Denhardt; Jin Jin; Rakesh Ganorkar; Melissa A VanAlstine; Chengyun Guo; Dana J Cohen; Jean M Bidlack
Journal:  Bioorg Med Chem Lett       Date:  2009-02-25       Impact factor: 2.823

7.  Synthesis and opioid receptor binding affinities of 2-substituted and 3-aminomorphinans: ligands for mu, kappa, and delta opioid receptors.

Authors:  Michael Decker; Yu-Gui Si; Brian I Knapp; Jean M Bidlack; John L Neumeyer
Journal:  J Med Chem       Date:  2010-01-14       Impact factor: 7.446

8.  Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 6: Opioid receptor binding properties of cyclic variants of 8-carboxamidocyclazocine.

Authors:  Mark P Wentland; Xufeng Sun; Dana J Cohen; Jean M Bidlack
Journal:  Bioorg Med Chem       Date:  2008-03-30       Impact factor: 3.641

9.  Agonist vs antagonist behavior of delta opioid peptides containing novel phenylalanine analogues in place of Tyr(1).

Authors:  Irena Berezowska; Nga N Chung; Carole Lemieux; Brian C Wilkes; Peter W Schiller
Journal:  J Med Chem       Date:  2009-11-12       Impact factor: 7.446

10.  Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. 5. Opioid receptor binding properties of N-((4'-phenyl)-phenethyl) analogues of 8-CAC.

Authors:  Melissa A VanAlstine; Mark P Wentland; Dana J Cohen; Jean M Bidlack
Journal:  Bioorg Med Chem Lett       Date:  2007-09-29       Impact factor: 2.823

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