Synthesis and analgesic activity of hydrochlorides and quaternary ammoniums of epibatidine incorporated with amino acid ester

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 24, 2003, Pages 4327-4329

  Dong, Jing Chao ^a   Wang, Xin ^a   Li, Run Tao ^a   Zhang, Hong Mei ^a   Cheng, Tie Ming ^a   Li, Chang Ling ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; ANTINOCICEPTIVE AGENT; CHLORIDE; EPIBATIDINE; EPIBATIDINE DERIVATIVE; ESTER DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; IN VIVO STUDY; MOUSE; NONHUMAN; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; RAT;

EID: 0344064848     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.09.047     Document Type: Article

References (30)

1. (a) Spande T.F., Garraffo H.M., Edwards M.W., Yeh H.J.C., Pannell L., Daly J.W. J. Am. Chem. Soc. 114:1992;3475 (b) Daly J.W. J. Nat. Prod. 6:1998;162.
2. (a) Li T.C., Qian C.G., Eckman J., Huang D.F., Shen T.Y. Bioorg. Med. Chem. Lett. 3:1993;2759 (b) Qian C.G., Li T.C., Shen T.Y., Libertinegarahan L., Eckman J., Biftu T., Ip S. Eur. J. Pharm. 250:1993;R13 (c) Fisher M., Huangfu D., Shen T.Y., Guyenet P.G. J. Pharmacol. Exp. Ther. 270:1994;702 (d) Badio B., Daly J.W. Mol. Pharm. 45:1994;563.
3. Sullivan J.P., Decker M.W., Brioni J.D., Donnelly-Roberts D., Anderson D.J., Bannon A.W., Kang C.-H., Adams P., Piattoni-Kaplan M., Buckley M.J., Gopalakrishnan M., Williams M., Arneric S.P. J. Pharmacol. Exp. Ther. 271:1994;624.
4. Bonhaus D.W., Bley K.R., Broka C.A., Fontana D.J., Leung E., Lewis R., Shieh A., Wong E.H.F. J. Pharmacol. Exp. Ther. 272:1995;1199.
5. Rao T.S., Correa L.D., Reid R.T., Lloyd G.K. Neuropharmacology. 35:1996;393.
6. Molina P.E., Ding Y.-S., Carroll F.I., Liang F., Volkow N.D., Pappas N., Kuhar M., Abumrad N., Gatley S.J., Fowler J.S. Nucl. Med. Biol. 24:1997;743.
7. Xu R., Bai D., Chu G., Tao J., Zhu X. Bioorg. Med. Chem. Lett. 6:1996;279.
8. Malpass J.R., Hemmings D.A., Wallis A.L. Tetrahedron Lett. 37:1996;3911.
9. Bai D., Xu R., Chu G., Zhu X. J. Org. Chem. 61:1996;4600.
10. Zhang C., Gyermek L., Trudell M.L. Tetrahedron Lett. 38:1997;5619.
11. Wright E., Gallagher T., Sharples C.G.V., Wonnacott S. Bioorg. Med. Chem. Lett. 7:1997;2867.
12. Bencherif, M.; Caldwell, W. S.; Dull, G. M.; Lippiello, P. M. US Patent 5583140, 1996.
13. Krow G.R., Cheung O.H., Hu Z., Huang Q., Hutchinson J., Liu N., Nguyen K.T., Ulrich S., Yuan J., Xiao Y., Wypij D.M., Zuo F., Carroll P.J. Tetrahedron. 55:1999;7747.
14. Holladay M.W., Dart M.J., Lynch J.K. J. Med. Chem. 40:1997;4169.
15. Seerden J.-P. G., Tulp M., Th M., Sheerren H.W., Kruse C.G. Bioorg. Med. Chem. 6:1998;2103.
16. Rádl S., Hezký P., Hafner W., Buděší nský M., Hejnová L. Bioorg. Med. Chem. Lett. 10:2000;55.
17. Che D., Wegge T., Stubbs M.T., Sertz G., Meier H., Methfessel C. J. Med. Chem. 44:2001;47.
18. Brieddy L.E., Mascarella S.W., Navarro H.A., Atkinson R.N., Damaj M.I., Martin B.R., Carroll F.I. Tetrahedron Lett. 42:2001;3795.
19. Cheng J., Zhang C., Stevens E.D., Izenwasser S., Wade D., Chen S., Paul D., Trudell M.L. J. Med. Chem. 45:2002;3041.
20. Kizawa Y., Takayanagi I. Gen. Pharmacol. 15:1984;149.
21. Lippiello P.M., Fernandes K.G. Mol. Pharmacol. 29:1986;448.
22. De Fiebre C.M., Meyer E.M., Henry J.C., Muraskin S.I., Kem W.R., Papke R.L. Mol. Pharmacol. 47:1995;164.
23. Romanelli M.N., Manetti D., Scapecchi S., Borea P.A., Dei S., Bartolini A., Ghelardini C., Gualtieri F., Guandalini L., Varani K. J. Med. Chem. 44:2001;3946.
24. Lin N.H., Meyer M.D. Exp. Opin. Ther. Pat. 8:1998;991.
25. Dwoskin L.P., Xu R., Ayers J.T., Crooks P.A. Exp. Opin. Ther. Pat. 10:2000;1561.
26. Boksa P., Quirion R. Eur. J. Pharmacol. 139:1987;323.
27. Manetti D., Bartolini A., Borea P.A., Bellucci C., Dei S., Ghelardini C., Gualtieri F., Romanelli M.N., Scapecchi S., Teodori E., Varani K. Bioorg. Med. Chem. 7:1999;457.
28. (a) Li R.T., Cao S.L., Chen H.C., Yang J.Z., Cai M.S. Acta Pharm. Sin. 31:1996;757 (b) Li R.T., Cui J.L., Cai M.S. Acta Pharm. Sin. 33:1998;28 (c) Li R.T., Cai J.C., Tang X.C., Cai M.S. Arch. Pharm. Pharm. Med. Chem. 332:1999;179 (d) Wang X., Gao F.L., Piao H.B., Cheng T.M., Li R.T. Bioorg. Med. Chem. Lett. 13:2003;1729 (e) Gao F.L., Wang X., Zhang H.M., Cheng T.M., Li R.T. Bioorg. Med. Chem. Lett. 13:2003;1535.
29. Dong J.C., Li R.T., Cheng T.M. Chinese. Chem. Lett. 12:2001;1061.
30. Pandey G., Bagul T.D., Sahoo A.K. J. Org. Chem. 63:1998;760.