2183-56-4Relevant articles and documents
PROCESS FOR MAKING MORPHINAN-6alpha-OLS
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Page/Page column 5, (2010/03/02)
The present invention provides a process whereby morphinan-6-ones can be converted stereospecifically to the corresponding morphinan-6α-ols by catalytic hydrogenation under basic conditions.
Probes for narcotic receptor mediated phenomena. 24. synthesis, single crystal X-ray analyses, in vitro and in vivo properties of 6α-and 6β-IODO-3,14-dihydroxy-17-methyl-4,5α-epoxymorphinans
Kayakiri, Hiroshi,Jacobson, Arthur E.,Rice, Kenner C.,Rothman, Richard B.,Xu, Heng,Flippen-Anderson, Judith L.,George, Clifford,Aceto, Mario D.,Bowman, Edward R.,Harris, Louis S.,May, Everette L.,Partilla, John S.,Becketts, Karen
, p. 427 - 438 (2007/10/03)
The 6α- and 6β-iodo-3,14-dihydroxy-17-methyl-4,5α-epoxymorphinans, potential SPECT ligands, were synthesized and found to be μ-selective opioids, more potent in vitro and in vivo than their 6-hydroxy relatives. Single-crystal analysis showed that the 6α- and 6β-iodine atoms are spatially closely located although the C-ring conformations of these compounds are quite different (twist-boat form vs. chair). These epimeric conformational differences were not reflected in their binding affinities.
Synthesis and utilization of 17-methyl and 17-cyclopropylmethyl-3,14-dihydroxy-4,5α-epoxy 6β-fluoromorphinans (foxy and cyclofoxy) as (18F)-labeled opioid ligands for position emission transaxial tomography (PETT)
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, (2008/06/13)
Fluorinated derivatives 3,14-dihydroxy-4,5α-epoxy-6β-fluoro-17-methylmorphinan (""fluorooxymorphone""; FOXY, compound 10) and 17-cyclopropylmethyl-3,14-dihydroxy-4,5α-epoxy-6β-fluoromorphinan (CYCLOFOXY, compound 18) are prepared based upon the structures of the potent opioid agonist oxymorphone 4 and the antagonist naltrexone 11, respectively. Fluorine was introduced in the final stages of synthesis by a facile nucleophilic displacement with fluoride ion of the 6α-triflate functions in 8 and 16. The synthetic procedures were suitable for the production of the corresponding positron emitting 18 F-labeled analogs 18 F-FOXY and 18 F-CYCLOFOXY, which are useful for in vivo studies of the opioid receptor system using positron emission transaxial tomography. In addition, the tritiation of FOXY (10) to high specific activity is noted.