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2005
Multi-membered N-heterocycles
R 0690
6'-Methylpyrido[3,4-b]norhomotropane: Synthesis and Outstanding Potency in
to the α4β2 Nicotinic Receptor Pharmacophore Model. — Title tropane
25- 167 Relation
(IV) is prepared from the earlier reported azabicyclononane (I) via Wacker oxidation
and ring closure reaction. The high potency of the conformationally restricted, bridged
nicotinoid (IV) makes it an excellent reference template for the pharmacophoric elements of other more flexible ligands. In considering possible molecular overlays, the
(1R)-enantiomer of (IV) is compared with natural (1R)-epibatine. The 6'-methyl group
of (IV) is equivalent to the acetyl methyl of acetylcholine. — (KANNE, D. B.;
TOMIZAWA, M.; DURKIN, K. A.; CASIDA*, J. E.; Bioorg. Med. Chem. Lett. 15
(2005) 4, 877-881; Environ. Chem. Toxicol. Lab., Dep. Environ. Sci. Policy Manage.,
Univ. Calif., Berkeley, CA 94720, USA; Eng.) — H. Hoennerscheid
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