Author(s)
S.
Frau, S.
Dall'Angelo, G. L.
Baillie, R. A.
Ross, M.
Pira, C. C.
Tseng, P.
Lazzari, M.
Zanda
ISBN
0022-1139
Publication year
2013
Periodical
Journal of Fluorine Chemistry
Periodical Number
Volume
152
Pages
166-172
Author Address
Zanda, M
Univ Aberdeen, Kosterlitz Ctr Therapeut, Inst Med Sci, Foresterhill AB25 2ZD, Scotland
Univ Aberdeen, Kosterlitz Ctr Therapeut, Inst Med Sci, Foresterhill AB25 2ZD, Scotland
Neurosci PharmaNess Scarl, I-09010 Pula, CA, Italy
Univ Sassari, Dipartimento Chim & Farm, I-07100 Sassari, SS, Italy
CNR ICRM, I-20131 Milan, Italy
A novel class of cannabinoid ligands was synthesized in good overall yields by means of oxime-bio-conjugation between hydroxylamine-functionalized Rimonabant-type pyrazoles and fluoro-deoxy-carbohydrates (D-2-fluoro-deoxy-glucose, FDG, and D-5-fluoro-5-deoxy-ribose, FDR). FDR proved to be superior to FDG for bio-conjugation, as it occurred in milder conditions and at faster rate (rt, 20 min vs. 100 degrees C, 30 min). All of the title compounds showed relatively modest affinity for the CBI receptor (high nanomolar range) and selectivities vs. the CB2. (C) 2013 Elsevier B.V. All rights reserved.