title: Synthesis and biological activity of 3-substituted 3-desoxynaltrindole derivatives.
abstract: The 3-unsubstituted and substituted analogs of naltrindole (NTI) were synthesized using palladium-catalyzed transformations, and their binding affinity to opioid receptors was determined. Although the 3-desoxy analog showed comparable delta selectivity with that of NTI, all of the novel compounds possessed low affinity for delta receptors indicating the important role of the 3-oxygen atom of NTI for interaction with delta-opioid receptors.
authors.affiliation: Laboratory of Medicinal Chemistry, National Institute of Diabetes, Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892, USA.
authors.forename: H
authors.initials: H
authors.lastname: Kubota
authors.forename: R B
authors.initials: RB
authors.lastname: Rothman
authors.forename: C
authors.initials: C
authors.lastname: Dersch
authors.forename: K
authors.initials: K
authors.lastname: McCullough
authors.forename: J
authors.initials: J
authors.lastname: Pinto
authors.forename: K C
authors.initials: KC
authors.lastname: Rice
mesh_terms: D000818:Animals; D044482:Benzeneacetamides; D001667:Binding, Competitive; D001921:Brain / Q000378:metabolism; D002462:Cell Membrane / Q000378:metabolism; D015195:Drug Design; D020875:Enkephalin, Ala(2)-MePhe(4)-Gly(5)-; D016308:Enkephalin, Leucine-2-Alanine / Q000378:metabolism; D004745:Enkephalins / Q000378:metabolism; D015394:Molecular Structure; D009271:Naltrexone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009292:Narcotic Antagonists / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011759:Pyrrolidines / Q000378:metabolism; D051381:Rats; D017465:Receptors, Opioid, delta / Q000187:drug effects / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D044482:Benzeneacetamides; D004745:Enkephalins; D009292:Narcotic Antagonists; D011759:Pyrrolidines; D017465:Receptors, Opioid, delta; D020875:Enkephalin, Ala(2)-MePhe(4)-Gly(5)-; D009271:Naltrexone; D016308:Enkephalin, Leucine-2-Alanine; C055382:naltrindole; C045444:U 69593