14-Desoxy analogues of naltrindole and 7-spiroindanyloxymorphone: the role of the 14-hydroxy group at delta opioid receptors.
The 14-hydroxy group is known to increase the antagonist potency of mu-selective opioid ligands. To investigate the role of this group at the delta opioid receptor, the 14-desoxy analogues (7 and 9) of the delta-selective ligands, naltrindole (1, NTI) and spiroindanyloxymorphone (2, SIOM), have been synthesized and tested. The in vitro pharmacologic activities of 7 and 9 suggest that the 14-hydroxy group plays an important role in determining the delta selectivity and potency of NTI and SIOM.
Kshirsagar
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Department of Medicinal Chemistry, College of Pharmacy, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Fang
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Portoghese
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D000818:Animals; D006168:Guinea Pigs; D007082:Ileum / Q000187:drug effects / Q000502:physiology; D066298:In Vitro Techniques; D008297:Male; D051379:Mice; D009119:Muscle Contraction / Q000187:drug effects; D009130:Muscle, Smooth / Q000187:drug effects; D009271:Naltrexone / Q000031:analogs & derivatives* / Q000494:pharmacology; D009292:Narcotic Antagonists / Q000494:pharmacology*; D010111:Oxymorphone / Q000031:analogs & derivatives* / Q000494:pharmacology; D017465:Receptors, Opioid, delta / Q000819:agonists* / Q000037:antagonists & inhibitors*; D013141:Spiro Compounds / Q000494:pharmacology*; D014649:Vas Deferens / Q000187:drug effects / Q000502:physiology
D009292:Narcotic Antagonists; D017465:Receptors, Opioid, delta; D013141:Spiro Compounds; C082822:7-spiroindanyloxymorphone; D009271:Naltrexone; D010111:Oxymorphone; C055382:naltrindole