96917-43-0Relevant articles and documents
Probes for narcotic receptor mediated phenomena. 11. Synthesis of 17-methyl and 17-cyclopropylmethyl-3,14-dihydroxy-4,5α-epoxy-6β-fluoromorphinans (foxy and cyclofoxy) as model of opioid ligands suitable for positron emission transaxial tomography
Burke, Terrence R.,Rice, Kenner C.,Pert, Candace B.
, p. 99 - 106 (2007/10/02)
Fluorinated derivatives 3,14-dihydroxy-4,5α-epoxy-6β-fluoro-17-methylmorphinan ("fluorooxymorphone": FOXY, 10) and 17-cyclopropylmethyl-3,14-dihydroxy-4,5α-epoxy-6β-fluoromorphnian (CYCLOFOXY, 18) were 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 are suitable for the production of the corresponding positron emitting 18F-labeled analogs 18F-FOXY and 18F-CYCLOFOXY, which may be usefuf 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 described