title: A selective delta opioid receptor antagonist based on a stilbene core.
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.
authors.affiliation: Department of Chemistry, The University of Iowa, Chemistry Building, Iowa City, IA 52242-1294, United States.
authors.forename: Alyssa M
authors.initials: AM
authors.lastname: Hartung
authors.affiliation: Discovery Sciences, RTI International, Research Triangle Park, NC 27709, United States.
authors.forename: Hernan A
authors.initials: HA
authors.lastname: Navarro
authors.affiliation: Department of Chemistry, The University of Iowa, Chemistry Building, Iowa City, IA 52242-1294, United States.
authors.forename: David F
authors.initials: DF
authors.lastname: Wiemer
authors.affiliation: Department of Chemistry, The University of Iowa, Chemistry Building, Iowa City, IA 52242-1294, United States; Department of Pharmacology, Pennsylvania State University Hershey College of Medicine, Hershey, PA 17033, United States; Penn State Hershey Cancer Institute, Hershey, PA 17033, United States.
authors.forename: Jeffrey D
authors.initials: JD
authors.lastname: Neighbors
mesh_terms: D006801:Humans; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D009292:Narcotic Antagonists / Q000138:chemical synthesis / Q000737:chemistry*; D017465:Receptors, Opioid, delta / Q000037:antagonists & inhibitors*; D013267:Stilbenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013729:Terpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D009292:Narcotic Antagonists; D017465:Receptors, Opioid, delta; D013267:Stilbenes; D013729:Terpenes; C482998:pawhuskin A; C482999:pawhuskin B
keywords: Delta receptor; Directed ortho metalation; Docking; Opioid; Pawhuskin