PROBES FOR NARCOTIC RECEPTOR-MEDIATED PHENOMENA .24. SYNTHESIS, SINGLE-CRYSTAL X-RAY ANALYSES, IN-VITRO AND IN-VIVO PROPERTIES OF -3,14-DIHYDROXY-17-METHYL-4,5-ALPHA-EPOXYMORPHINAN AND -3,14-DIHYDROXY-17-METHYL-4,5-ALPHA-EPOXYMORPHINAN

Authors
KAYAKIRI H JACOBSON AE RICE KC ROTHMAN RB XU H FLIPPENANDERSON JL GEORGE C ACETO MD BOWMAN ER HARRIS LS MAY EL PARTILLA JS BECKETTS K
Citation
H. Kayakiri et al., PROBES FOR NARCOTIC RECEPTOR-MEDIATED PHENOMENA .24. SYNTHESIS, SINGLE-CRYSTAL X-RAY ANALYSES, IN-VITRO AND IN-VIVO PROPERTIES OF -3,14-DIHYDROXY-17-METHYL-4,5-ALPHA-EPOXYMORPHINAN AND -3,14-DIHYDROXY-17-METHYL-4,5-ALPHA-EPOXYMORPHINAN, Medicinal chemistry research, 6(6), 1996, pp. 427-438
Citations number
21
Categorie Soggetti
Chemistry Medicinal
Journal title
Medicinal chemistry research → ACNP
ISSN journal
10542523
Volume
6
Issue
6
Year of publication
1996
Pages
427 - 438
Database
ISI
SICI code
1054-2523(1996)6:6<427:PFNRP.>2.0.ZU;2-6
Abstract
The 6 alpha- and 6 beta-iodo-3,14-dihydroxy-17-methyl-4,5 alpha-epoxym orphinans, potential SPECT ligands, were synthesized and found to be m u-selective opioids, more potent in vitro and in vivo than their 6-hyd roxy relatives. Single-crystal analysis showed that the 6 alpha- and 6 beta-iodine atoms are spatially closely located although the C-ring c onformations of these compounds are quite different (twist-boat form v s. chair). These epimeric conformational differences were not reflecte d in their binding affinities.