Derivatives of 17-(2-methylallyl)-substituted noroxymorphone: variation of the delta address and its effects on affinity and selectivity for the delta opioid receptor.
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.
Ullrich
T
T
Laboratory of Medicinal Chemistry, NIDDK, National Institutes of Health, Bethesda, MD 20892, USA.
Dersch
C M
CM
Rothman
R B
RB
Jacobson
A E
AE
Rice
K C
KC
D010111:Oxymorphone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism*; D011869:Radioligand Assay; D017465:Receptors, Opioid, delta / Q000378:metabolism*
D017465:Receptors, Opioid, delta; D010111:Oxymorphone