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. 2008 Jan 15;16(2):746-54.
doi: 10.1016/j.bmc.2007.10.027. Epub 2007 Oct 13.

Synthesis, nicotinic acetylcholine receptor binding, and pharmacological properties of 3'-(substituted phenyl)deschloroepibatidine analogs

F Ivy Carroll  1 , Yasuno Yokota, Wei Ma, Jeffrey R Lee, Lawrence E Brieaddy, Jason P Burgess, Hernán A Navarro, M I Damaj, Billy R Martin
Affiliations

Synthesis, nicotinic acetylcholine receptor binding, and pharmacological properties of 3'-(substituted phenyl)deschloroepibatidine analogs

F Ivy Carroll et al. Bioorg Med Chem. .

Abstract

A series of 3'-(substituted phenyl)deschloroepibatidine analogs (5a-j) were synthesized. The alpha4beta2( *) and alpha7 nicotinic acetylcholine receptor (nAChR) binding properties and functional activity in the tail-flick, hot-plate, locomotor, and body temperature tests in mice of 5a-j were compared to those of the nAChR agonist, nicotine (1), epibatidine (4), and deschloroepibatidine (13), the partial agonist, varenicline (3), and the antagonist 2'-fluoro-3'-(substituted phenyl)deschloroepibatidine analogs (7a-j). Unlike epibatidine and deschloroepibatidine, which are potent agonists in the tail-flick test, 5a-k show no or very low antinociceptive activity in the tail-flick or hot-plate test. However, they are potent antagonists in nicotine-induced antinociception in the tail-flick test, but weaker than the corresponding 2'-fluoro-3'-(substituted phenyl)deschloroepibatidines.

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Figures

Scheme 1
Scheme 1
Reagents: (a) Pd(OAc)2, P(o-tolyl)3, Na2CO3, (X,Y)C6H4B(OH)2 DME; (b)CF3CO2H; (c)Fe, HCl(H2O).
Scheme 1
Scheme 1
Reagents: (a) Pd(OAc)2, P(o-tolyl)3, Na2CO3, (X,Y)C6H4B(OH)2 DME; (b)CF3CO2H; (c)Fe, HCl(H2O).
Scheme 2
Scheme 2
Reagents: (a) Pd(OAc)2, P(o-tolyl)3, Na2CO3, DME, H2O, 3-NO2C6H4B(OH)2 or CH3OC6H4B(OH)2; (b) NaNO2, HCl;(c)10% Pd/C, CH3OH.
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