title: The role of the side chain in determining relative delta- and kappa-affinity in C5'-substituted analogues of naltrindole.
abstract: The role of the side chain in 5'-substituted analogues of naltrindole has been further explored with the synthesis of series of amides, amidines, and ureas. Amidines (8, 13) had greatest selectivity for the kappa receptor, as predicted from consideration of the message-address concept. It was also found that an appropriately located carbonyl group, in ureas (10) and amides (7), led to retention of affinity and antagonist potency at the delta receptor.
authors.affiliation: Department of Pharmacy and Pharmacology, University of Bath, Bath, BA2 7AY, UK.
authors.forename: Shannon L
authors.initials: SL
authors.lastname: Black
authors.forename: Andrew R
authors.initials: AR
authors.lastname: Jales
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Brandt
authors.forename: John W
authors.initials: JW
authors.lastname: Lewis
authors.forename: Stephen M
authors.initials: SM
authors.lastname: Husbands
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000578:Amidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D016466:CHO Cells; D006224:Cricetinae; D006801:Humans; D009271:Naltrexone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009292:Narcotic Antagonists / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011869:Radioligand Assay; D017465:Receptors, Opioid, delta / Q000037:antagonists & inhibitors* / Q000378:metabolism; D017473:Receptors, Opioid, kappa / Q000037:antagonists & inhibitors* / Q000378:metabolism; D014508:Urea / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000577:Amides; D000578:Amidines; D009292:Narcotic Antagonists; D017465:Receptors, Opioid, delta; D017473:Receptors, Opioid, kappa; D009271:Naltrexone; D014508:Urea; C055382:naltrindole