Synthesis of two fluoro analogues of the nicotinic acetylcholine receptor agonist UB-165.

Andrew Sutherland, Timothy Gallagher, Christopher G V Sharples, Susan Wonnacott

Index: J. Org. Chem. 68(6) , 2475-8, (2003)

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Abstract

Two racemic fluoropyridine analogues 4 and 5 of the potent nicotinic agonist UB-165 have been synthesized. Halogenated pyridines 7 and 12 provided the organometallic reagents needed for the Negishi and Suzuki coupling reactions used for the preparation of 4 and 5, and the N-vinyloxycarbonyl protecting group of 8 and 15 was cleaved using a novel trifluoroacetic acid-mediated deprotection protocol. Analogue 4 retained high binding affinity at rat brain alpha4beta2 and alpha7 nicotinic receptors.