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Literature DB >> 26525865

A selective delta opioid receptor antagonist based on a stilbene core.

Alyssa M Hartung¹, Hernan A Navarro², David F Wiemer¹, Jeffrey D Neighbors³.

Abstract

Studies of directed ortho metalation reactions on an aromatic substrate with multiple potential directing groups have identified conditions that favor either of two regioisomers. One of these regioisomers has been converted to an analogue of the stilbene pawhuskin A, and been shown to have high selectivity as an antagonist of the delta opioid receptor. Docking studies have suggested that this compound can adopt a conformation similar to naltrindole, a known delta antagonist.

Entities: Chemical Disease Gene Species

Keywords: Delta receptor; Directed ortho metalation; Docking; Opioid; Pawhuskin

Mesh：

Substances：

Year: 2015 PMID： 26525865 PMCID： PMC4645280 DOI： 10.1016/j.bmcl.2015.10.059

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

18 in total

1. UCSF Chimera--a visualization system for exploratory research and analysis.

Authors: Eric F Pettersen; Thomas D Goddard; Conrad C Huang; Gregory S Couch; Daniel M Greenblatt; Elaine C Meng; Thomas E Ferrin
Journal: J Comput Chem Date: 2004-10 Impact factor: 3.376

2. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading.

Authors: Oleg Trott; Arthur J Olson
Journal: J Comput Chem Date: 2010-01-30 Impact factor: 3.376

3. Naltrindole derivatives with fluorinated ethyl substituents on the 17-nitrogen as δ opioid receptor inverse agonists.

Authors: Toru Nemoto; Yusuke Iihara; Shigeto Hirayama; Takashi Iwai; Eika Higashi; Hideaki Fujii; Hiroshi Nagase
Journal: Bioorg Med Chem Lett Date: 2015-05-22 Impact factor: 2.823

Review 4. Neoclerodanes as atypical opioid receptor ligands.

Authors: Thomas E Prisinzano
Journal: J Med Chem Date: 2013-04-18 Impact factor: 7.446

5. Exploration of cascade cyclizations terminated by tandem aromatic substitution: total synthesis of (+)-schweinfurthin A.

Authors: Joseph J Topczewski; John G Kodet; David F Wiemer
Journal: J Org Chem Date: 2011-01-12 Impact factor: 4.354

6. New geranyl stilbenes from Dalea purpurea with in vitro opioid receptor affinity.

Authors: Gil Belofsky; April N French; David R Wallace; Summer L Dodson
Journal: J Nat Prod Date: 2004-01 Impact factor: 4.050

7. A concise synthesis of pawhuskin A.

Authors: Jeffrey D Neighbors; Matthew J Buller; Kelly D Boss; David F Wiemer
Journal: J Nat Prod Date: 2008-10-15 Impact factor: 4.050

8. Pharmacology and anti-addiction effects of the novel κ opioid receptor agonist Mesyl Sal B, a potent and long-acting analogue of salvinorin A.

Authors: B Simonson; A S Morani; A W M Ewald; L Walker; N Kumar; D Simpson; J H Miller; T E Prisinzano; B M Kivell
Journal: Br J Pharmacol Date: 2014-07-01 Impact factor: 8.739

A selective delta opioid receptor antagonist based on a stilbene core.

1. UCSF Chimera--a visualization system for exploratory research and analysis.

2. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading.

3. Naltrindole derivatives with fluorinated ethyl substituents on the 17-nitrogen as δ opioid receptor inverse agonists.

Review 4. Neoclerodanes as atypical opioid receptor ligands.

5. Exploration of cascade cyclizations terminated by tandem aromatic substitution: total synthesis of (+)-schweinfurthin A.

6. New geranyl stilbenes from Dalea purpurea with in vitro opioid receptor affinity.

7. A concise synthesis of pawhuskin A.

8. Pharmacology and anti-addiction effects of the novel κ opioid receptor agonist Mesyl Sal B, a potent and long-acting analogue of salvinorin A.

9. Structure of the δ-opioid receptor bound to naltrindole.

10. Stilbenes as κ-selective, non-nitrogenous opioid receptor antagonists.

1. Selective opioid growth factor receptor antagonists based on a stilbene isostere.

2. Substitution of a triazole for the central olefin in biologically active stilbenes.