Synthesis and nicotinic receptor activity of a hydroxylated tropane

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 1, 2004, Pages 271-273

  Bremner, John B ^a   Godfrey, Colette A ^a   Jensen, Anders A ^b   Smith, Reginald J ^c  

^a UNIVERSITY OF WOLLONGONG   (Australia)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

^c Phytex Australia Pty Ltd   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

3 ALPHA HYDROXYHOMOEPIBATIDINE; EPIBATIDINE; NICOTINE; NICOTINIC RECEPTOR; SCOPOLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG SELECTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROXYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN SYNTHESIS;

EID: 0348147632     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.09.081     Document Type: Article

References (15)

1. Dart M.J., Wasicak J.T., Ryther K.B., Schrimpf M.R., Kim K.H., Anderson D.J., Sullivan J.P., Meyer M.D. Pharm. Acta. Helvet. 74:2000;115.
2. Lloyd G.K., Williams M. J. Pharmacol. Exp. Ther. 292:2000;461.
3. Astles P.C., Baker S.R., Boot J.R., Broad L.M., Dell C.P., Keenan M. Curr. Drug Targets CNS Neurol. Disorders. 1:2002;337.
4. Bencherif M., Schmitt J.D. Curr. Drug Targets CNS Neurol. Disorders. 1:2002;349.
5. Barlocco D., Cignarella G., Tondi D., Vianello P., Villa S., Bartolini A., Ghelardini C., Galeotti N., Anderson D.J., Kuntzweiler T.A., Colombo D., Toma L. J. Med. Chem. 41:1998;674.
6. For further ring analogues, see: Toma L., Quadrelli P., Bunnelle W.H., Anderson D.J., Meyer M.D., Cignarella G., Gelain A., Barlocco D. J. Med. Chem. 45:2002;4011.
7. Bannon A.W., Decker M.W., Holladay M.W., Curzon P., Donnelly-Roberts D., Puttfarcken P.S., Bitner R.S., Diaz A., Dickenson A.H., Porsolt R.D., Williams M., Arneric S.P. Science. 279:1998;77.
8. Malpass J.R., Hemmings D.A., Wallis A.L., Fletcher S.R., Patel S. J. Chem. Soc., Perkin Trans. 1. 1044:2001.
9. Xu R., Bai D., Chu G., Tao J., Zhu X. Bioorg. Med. Chem. Lett. 6:1996;279.
10. For recently published hydroxylated epibatidine analogues see: Wei Z.-L., George C., Kozikowski A.P. Tetrahedron Lett. 44:2003;3847.
11. Bremner J.B., Smith R.J., Tarrant G.J. Tetrahedron Lett. 37:1996;97.
12. Aberle N.S., Ganesan A., Lambert J.N., Sauber S., Smith R. Tetrahedron Lett. 42:2001;1975.
13. 3OD) δ 8.27 (1H, d, J=2.7 Hz, H2′), 7.79 (1H, dd, J=8.7 Hz, J=2.7 Hz, H4′), 7. 36 (1H, d, J=7.8 Hz, H5′), 4.08 (1H, t, J=4.5 Hz, H3), 4.02 (1H, dd, J=9. 3 Hz, J=5.4 Hz, H6), 3.70-3.65 (1H, m, H1), 3.38 (1H, t, J=3.0 Hz, H5), 2.76 (1H, dd, J=12.9 Hz, J=9.3 Hz, H7a), 2.08-1.99 (3H, m, H4e, H2a/e), 1.88-1.81 (2H, m, H7e, H4a).
14. Bai D., Xu R., Chu G., Zhu X. J. Org. Chem. 61:1996;4600.
15. Jensen A.A., Mikkelsen I., Frølund B., Bräuner-Osborne H., Falch E., Krogsgaard-Larsen P. Mol. Pharmacol. 64:2003;1.