Synthesis and binding of 6,7,8,9-tetrahydro-5H-pyrido[3,4-d]azepine and related ring-opened analogs at central nicotinic receptors

European Journal of Medicinal Chemistry

Volumn 34, Issue 2, 1999, Pages 177-190

  Cheng, Yun Xing ^a   Dukat, Malgorzata ^a   Dowd, Matthew ^a   Fiedler, Wolfgang ^a   Martin, Billy ^a   Damaj, Mohamed Imad ^a   Glennon, Richard A ^a  

^a VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

3 (2 Aminoethoxy)pyridines; 3 (2 Aminoethyl)pyridines; Nicotine receptors; Nicotinic cholinergic receptors; Pyrido 3,4 c azepines; Pyrido 3,4 d azepines

Indexed keywords

6,7,8,9 TETRAHYDRO 5H PYRIDO[3,4 D]AZEPINE; AZEPINE DERIVATIVE; CHOLINERGIC RECEPTOR; LIGAND; NICOTINE; NICOTINIC RECEPTOR; NITROGEN; NORNICOTINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS;

EID: 0032719341     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0223-5234(99)80051-8     Document Type: Article

References (28)

1. Williams M., Sullivan J.P., Arneric S.P. Drug News Perspect. 7:1994;205-223.
2. Dukat M., Fiedler W., Dumas D., Damaj I., Martin B., Rosecrans J.A., James J.R., Glennon R.A. Eur. J. Med. Chem. 31:1996;875-888.
3. Glennon R.A., Herndon J.L., Dukat M. Med. Chem. Res. 4:1994;461-473.
4. Kao C.H. K'o Hsueh T'ung Pao. 55:1957;434-436 Chem. Abstr. 55:1961;23522.
5. Kao C.H. K'o Hsueh T'ung Pao. 55:1957;434-436 Chem. Abstr. 55:1961;23522.
6. Shiao M.J., Chia W.L., Peng C.J., Shen C.C. J. Org. Chem. 58:1993;3162-3164.
7. Barlow R.B., Hamilton J.T., Brit. J. Pharmacol. 18 (1962) 510-542.
8. Sidler D.R., Lovelace T.C., McNamara J.M., Reider P.J. J. Org. Chem. 59:1994;1231-1233.
9. Levin J.I., Turos E., Weinreb S.M. Synth. Commun. 12:1982;989-993.
10. Katritzky A.R. J. Chem. Soc. 1955;2581-2586.
11. Sestanj K., Melenski E., Jirkovsky I. Tetrahedron Lett. 35:1994;5417-5420.
12. Roemmele R.C., Rapoport H. J. Org. Chem. 53:1988;2367-2371.
13. Rondhal L. Acta Pharm. Suecica. 13:1976;229-234.
14. Graef E., Frederickson J.M., Burger A. J. Org. Chem. 11:1945;257-267.
15. Mertes M.P., Borne R.E., Hare L.E. J. Heterocyclic Chem. 5:1968;281-283.
16. Carlson L.A., Hedbonn C., Helgstrand E., Misiorny A., Sjöberg B., Stjernström N.E., Westin G. Acta Pharm. Suecica. 9:1972;411-418.
17. Sakakibara M., Matsui M. Agricult. Biol. Chem. 43:1979;117-123.
18. Still W.C., Gennari C. Tetrahedron Lett. 24:1983;4405-4408.
19. Gobel G.W., Cram D.J. J. Org. Chem. 39:1974;2445-2446.
20. Bleicher L., Cosford N.D.P. Syn. Lett. 1995;1115-1116.
21. Harris M.A., McMillan I., Nayler J., Osborne N., Pearson M.J., Southgate R. J. Chem. Soc. Perkin I. 1976;1612-1615.
22. Holladay M.W., Lebold S.A., Lin N.H. Drug Dev. Res. 35:1995;191-213.
23. Kanne D.B., Abood L.G. J. Med. Chem. 31:1988;506-509.
24. Caldwell W.S., Benchenif M., Bhatti B.S., Deo N.M., Dobson G.P., Dull G.M., Lipiello P.M., Lovette M.E., Miller C.H., Ravard A., Schmitt J.D., Crooks P.A. Abstracts of the International Business Communications Symposium on Nicotinic Acetylcholine Receptors as Pharmaceutical Targets, Washington DC. July 24-25, 1997.
25. Abreo M.A., Lin N.H., Garvey D.S., Gunn D.E., Hettinger A.M., Wasicak J.T., Pavlik P.A., Martin Y.C., Donnelly-Roberts D.L., Anderson D.J., Sullivan J.P., Williams M., Arneric S.P., Holladay M.W. J. Med. Chem. 39:1996;817-825.
26. Scimeca J.A., Martin B.R. J. Pharm. Pharmacol. 40:1988;793-797.
27. Munson P.J., Rodbard D. Anal. Biochem. 107:1980;220-239.
28. Cheng Y.C., Prusoff W.H. Biochem. Pharmacol. 22:1973;3099-3108.