title: Derivatives of 17-(2-methylallyl)-substituted noroxymorphone: variation of the delta address and its effects on affinity and selectivity for the delta opioid receptor.
abstract: In an effort to establish the importance of the N-(2-methylallyl) substituent in the noroxymorphone series, several derivatives have been synthesized, retaining that N-substituent and modifying the delta address moiety. A few compounds showed moderate binding affinity and selectivity for the delta receptor; none displayed a pharmacological profile as exceptional as N-(2-methylallyl)noroxymorphindole. A second study showed that 3-O-methylation of all derivatives decreases binding affinity. The present results indicate that only a combination of the N-(2-methylallyl) group and an indole delta address provided high selectivity for the delta receptor.
authors.affiliation: Laboratory of Medicinal Chemistry, NIDDK, National Institutes of Health, Bethesda, MD 20892, USA.
authors.forename: T
authors.initials: T
authors.lastname: Ullrich
authors.forename: C M
authors.initials: CM
authors.lastname: Dersch
authors.forename: R B
authors.initials: RB
authors.lastname: Rothman
authors.forename: A E
authors.initials: AE
authors.lastname: Jacobson
authors.forename: K C
authors.initials: KC
authors.lastname: Rice
mesh_terms: D010111:Oxymorphone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism*; D011869:Radioligand Assay; D017465:Receptors, Opioid, delta / Q000378:metabolism*
chemical_list: D017465:Receptors, Opioid, delta; D010111:Oxymorphone