1724 Journal of Medicinal Chemistry, 2005, Vol. 48, No. 6
Letters
(7) Ferretti, G.; Dukat, M.; Giannella, M.; Piergentili, A.; Pigini,
M.; Quaglia, W.; Damaj, M. I.; Martin, B. R.; Glennon, R. A.
Binding of nicotine and homoazanicotine analogues at neuronal
nicotinic acetylcholinergic (nACh) receptors. Bioorg. Med. Chem.
Lett. 2003, 13, 733-735.
(8) (a) Tønder, J. E.; Olesen, P. H. Agonists at the R4â2 nicotinic
acetylcholine receptors: structure-activity relationships and
molecular modelling. Curr. Med. Chem. 2001, 8, 651-674. (b)
Carroll, F. I.; Lee, J. R.; Navarro, H. A.; Ma, W.; Brieaddy, L.
E.; Abraham, P.; Damaj, M. I.; Martin, B. R. Synthesis, nicotinic
acetylcholine receptor binding, and antinociceptive properties
of 2-exo-2-(2′,3′-disubstituted 5′-pyridinyl)-7-azabicyclo[2.2.1]-
heptanes: epibatidine analogues. J. Med. Chem. 2002, 45, 4755-
4761.
Menzaghi, F.; Rao, T. S.; Reid, R.; Sacaan, A. I.; Santori, E.;
Stauderman, K. A.; Whelan, K.; Lloyd, G. K.; McDonald, I. A.
(S)-(-)-5-Ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine Maleate
(SIB-1508Y): A novel anti-Parkinsonian agent with selectivity
for neuronal nicotinic acetylcholine receptors. J. Med. Chem.
1996, 39, 3235-3237.
(15) Carroll, F. I.; Lee, J. R.; Navarro, H. A.; Brieaddy, L. E.;
Abraham, P.; Damaj, M. I.; Martin, B. R. Synthesis, nicotinic
acetylcholine receptor binding, and antinociceptive properties
of 2-exo-2-(2′-substituted-3′-phenyl-5′-pyridinyl)-7-azabicyclo-
[2.2.1]heptanes. Novel nicotinic antagonists. J. Med. Chem.
2001, 44, 4039-4041.
(16) (a) Carroll, F. I.; Liang, F.; Navarro, H. A.; Brieaddy, L. E.;
Abraham, P.; Damaj, M. I.; Martin, B. R. Synthesis, nicotinic
acetylcholine receptor binding, and antinociceptive properties
of 2-exo-2-(2′-substituted 5′-pyridinyl)-7-azabicyclo[2.2.1]heptanes.
Epibatidine analogues. J. Med. Chem. 2001, 44, 2229-2237. (b)
Badio, B.; Daly, J. W. Epibatidine, a potent analgetic and
nicotinic agonist. Mol. Pharmacol. 1994, 45, 563-569.
(17) Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart,
W. E.; Belew, R. K.; Olson, A. J. Automated docking using a
Lamarckian genetic algorithm and empirical binding free energy
function. J. Comput. Chem. 1998, 19, 1639-1662.
(18) Le Nove`re, N.; Grutter, T.; Changeux, J.-P. Models of the
extracellular domain of the nicotinic receptors and of agonist-
and Ca2+-binding sites. Proc. Natl. Acad. Sci. U.S.A. 2002, 99,
3210-3215.
(19) Brejc, K.; van Dijk, W. J.; Klaassen, R. V.; Schuurmans, M.; van
der Oost, J.; Smit, A. B.; Sixma, T. K. Crystal structure of an
ACh-binding protein reveals the ligand-binding domain of
nicotinic receptors. Nature 2001, 411, 269-276.
(9) (a) Lin, N.-H.; Li, Y.; He, Y.; Holladay, M. W.; Kuntzweiler, T.;
Anderson, D. J.; Campbell, J. E.; Arneric, S. P. Synthesis and
structure-activity relationships of 5-substituted pyridine ana-
logues of 3-[2-((S)-pyrrolidinyl)methoxy]pyridine, A-84543:
A
potent nicotinic receptor ligand. Bioorg. Med. Chem. Lett. 2001,
11, 631-633. (b) Lin, N.-H.; Gunn, D. E.; Li, Y.; He, Y.; Bai, H.;
Ryther, K. B.; Kuntzweiler, T.; Donnelly-Roberts, D. L.; Ander-
son, D. J.; Campbell, J. E.; Sullivan, J. P.; Arneric, S. P.;
Holladay, M. W. Synthesis and structure-activity relationships
of pyridine-modified analogs of 3-[2-((S)-pyrrolidinyl)methoxy]-
pyridine, A-84543, a potent nicotinic acetylcholine receptor
agonist. Bioorg. Med. Chem. Lett. 1998, 8, 249-252.
(10) Gotti, C.; Carbonnelle, E.; Moretti, M.; Zwart, R.; Clementi, F.
Drugs selective for nicotinic receptor subtypes: a real possibility
or a dream? Behav. Brain Res. 2000, 113, 183-192.
(11) Xiao, Y.; Kellar, K. J. The comparative pharmacology and up-
regulation of rat neuronal nicotinic receptor subtype binding
sites stably expressed in transfected mammalian cells. J. Phar-
macol. Exp. Ther. 2004, 310, 98-107.
(12) Kellar, J. K.; Xiao, Y.; Hernandez, S. C.; Perry, D. C. Compara-
tive pharmacology and distribution of heteromeric neuronal
nicotinic receptors. Abstracts in Program Book, Neuronal Nico-
tinic Receptors and Ligands: Targets for Medication; NIDA,
NIH: Bal Harbour, FL, 2003.
(20) Costa, V.; Nistri, A.; Cavalli, A.; Carloni, P. A structural model
of agonist binding to the R3â4 neuronal nicotinic receptor. Br.
J. Pharmacol. 2003, 140, 921-931.
(21) Zhang, Y.; Pavlova, O. A.; Chefer, S. I.; Hall, A. W.; Kurian, V.;
Brown, L. L.; Kimes, A. S.; Mukhin, A. G.; Horti, A. G.
5-Substituted derivatives of 6-halogeno-3-((2-(S)-azetidinyl)-
methoxy)pyridine and 6-halogeno-3-((2-(S)-pyrrolidinyl)methoxy)-
pyridine with low picomolar affinity for R4â2 nicotinic acetyl-
choline receptor and wide range of lipophilicity: Potential probes
for imaging with positron emission tomography. J. Med. Chem.
2004, 47, 2453-2465.
(22) (a) Schapira, M.; Abagyan, R.; Totrov, M. Structural model of
nicotinic acetylcholine receptor isotypes bound to acetylcholine
and nicotine. BMC Struct. Biol. 2002, 2, 1. (b) Dutertre, S.;
Lewis, R. J. Computational approaches to understand R-cono-
toxin interactions at neuronal nicotinic receptors. Eur. J. Bio-
chem. 2004, 271, 2327-2334.
(13) (a) Wei, Z.-L.; Petukhov, P. A.; Xiao, Y.; Tu¨ckmantel, W.; George,
C.; Kellar, K. J.; Kozikowski, A. P. Synthesis, nicotinic acetyl-
choline receptor binding affinities, and molecular modeling of
constrained epibatidine analogues. J. Med. Chem. 2003, 46,
921-924. (b) Wei, Z.-L.; Xiao, Y.; George, C.; Kellar, K. J.;
Kozikowski, A. P. Functionalization of the alicyclic skeleton of
epibatidine: synthesis and nicotinic acetylcholine receptor bind-
ing affinities of epibatidine analogues. Org. Biomol. Chem. 2003,
1, 3878-3881. (c) Wei, Z.-L.; Xiao, Y.; Kellar, K. J.; Kozikowski,
A. P. Synthesis and pharmacological characterization of bivalent
ligands of epibatidine at neuronal nicotinic acetylcholine recep-
tors. Bioorg. Med. Chem. Lett. 2004, 14, 1855-1858.
(14) Cosford, N. D. P.; Bleicher, L.; Herbaut, A.; McCallum, J. S.;
Vernier, J.-M.; Dawson, H.; Whitten, J. P.; Adams, P.; Chavez-
Noriega, L.; Correa, L. D.; Crona, J. H.; Mahaffy, L. S.;
JM0492406