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

Full version

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.