Literature DB >> 15887972

A new structural motif for mu-opioid antagonists.

Isabelle Van den Eynde1, Georges Laus, Peter W Schiller, Piotr Kosson, Nga N Chung, Andrzej W Lipkowski, Dirk Tourwé.   

Abstract

On the basis of the structural features of the Dmt-Tic pharmacophore, a new motif leading to a fairly potent mu-opioid antagonist is described. This motif contains the 4-amino-1,2,4,5-tetrahydro-2-benzazepine-3-one skeleton as a substitute for the Tic residue, which provides the conformational constraint compatible with the mu-opioid receptor. The stereoselective synthesis of four stereoisomers is performed starting from homochiral 2',6'-dimethyltyrosine (Dmt) and o-aminomethylphenylalanine.

Entities:  

Mesh：

Substances：

Year:  2005        PMID： 15887972     DOI： 10.1021/jm0491795

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


  7 in total

1.  Effect of lysine at C-terminus of the Dmt-Tic opioid pharmacophore.

Authors:  Gianfranco Balboni; Valentina Onnis; Cenzo Congiu; Margherita Zotti; Yusuke Sasaki; Akihiro Ambo; Sharon D Bryant; Yunden Jinsmaa; Lawrence H Lazarus; Claudio Trapella; Severo Salvadori
Journal:  J Med Chem       Date:  2006-09-07       Impact factor: 7.446

2.  Conversion of the potent delta-opioid agonist H-Dmt-Tic-NH-CH(2)-bid into delta-opioid antagonists by N(1)-benzimidazole alkylation(1).

Authors:  Gianfranco Balboni; Remo Guerrini; Severo Salvadori; Lucia Negri; Elisa Giannini; Sharon D Bryant; Yunden Jinsmaa; Lawrence H Lazarus
Journal:  J Med Chem       Date:  2005-12-29       Impact factor: 7.446

3.  Design of novel neurokinin 1 receptor antagonists based on conformationally constrained aromatic amino acids and discovery of a potent chimeric opioid agonist-neurokinin 1 receptor antagonist.

Authors:  Steven Ballet; Debby Feytens; Koen Buysse; Nga N Chung; Carole Lemieux; Suneeta Tumati; Attila Keresztes; Joost Van Duppen; Josephine Lai; Eva Varga; Frank Porreca; Peter W Schiller; Jozef Vanden Broeck; Dirk Tourwé
Journal:  J Med Chem       Date:  2011-03-17       Impact factor: 7.446

4.  New 2',6'-dimethyl-L-tyrosine (Dmt) opioid peptidomimetics based on the Aba-Gly scaffold. Development of unique mu-opioid receptor ligands.

Authors:  Steven Ballet; Severo Salvadori; Claudio Trapella; Sharon D Bryant; Yunden Jinsmaa; Lawrence H Lazarus; Lucia Negri; Elisa Giannini; Roberta Lattanzi; Dirk Tourwé; Gianfranco Balboni
Journal:  J Med Chem       Date:  2006-06-29       Impact factor: 7.446

5.  Synthesis and biological evaluation of compact, conformationally constrained bifunctional opioid agonist - neurokinin-1 antagonist peptidomimetics.

Authors:  Karel Guillemyn; Patrycia Kleczkowska; Anna Lesniak; Jolanta Dyniewicz; Olivier Van der Poorten; Isabelle Van den Eynde; Attila Keresztes; Eva Varga; Josephine Lai; Frank Porreca; Nga N Chung; Carole Lemieux; Joanna Mika; Ewelina Rojewska; Wioletta Makuch; Joost Van Duppen; Barbara Przewlocka; Jozef Vanden Broeck; Andrzej W Lipkowski; Peter W Schiller; Dirk Tourwé; Steven Ballet
Journal:  Eur J Med Chem       Date:  2014-12-19       Impact factor: 6.514

6.  Novel selective human melanocortin-3 receptor ligands: use of the 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one (Aba) scaffold.

Authors:  Steven Ballet; Alexander V Mayorov; Minying Cai; Dagmara Tymecka; Kevin B Chandler; Erin S Palmer; Karolien Van Rompaey; Aleksandra Misicka; Dirk Tourwé; Victor J Hruby
Journal:  Bioorg Med Chem Lett       Date:  2007-02-09       Impact factor: 2.823

Review 7.  Peptidomimetics and Their Applications for Opioid Peptide Drug Discovery.

Authors:  Yeon Sun Lee
Journal:  Biomolecules       Date:  2022-09-05
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.