Synthesis of quinoline derivatives as 5-HT4 receptor ligands

Australian Journal of Chemistry

Volumn 62, Issue 2, 2009, Pages 150-156

  Hanna Elias, Amir ^a   Manallack, David T ^a   Berque Bestel, Isabelle ^b,c   Irving, Helen R ^a   Coupar, Ian M ^a   Iskander, Magdy N ^a  

^a MONASH UNIVERSITY   (Australia)

^b INSERM U869   (France)

^c UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHELATION; CYCLIZATION; SCAFFOLDS;

LEAD STRUCTURE; MALONATES; QUINOLINE DERIVATIVE; RECEPTOR LIGANDS; TETRAHYDROQUINOLINE;

LEAD COMPOUNDS;

EID: 60749088693     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH08505     Document Type: Article

References (19)

1. M. Ruth, B. Hamelin, K. Rohss, L. Lundell, Aliment. Pharmacol Ther. 1998, 12, 35. doi:10.1046/J.1365-2036.1998.00268.X
2. W. E. Whitehead B. T. Engel, M. M. Schuster, Dig. Dis. Sci. 1980, 25, 404. doi:10.1007/BF01395503
3. M. Tonini, S. M. Candura, Trends Pharmacol. Sci. 1996, 17, 314.
4. M. A. Kamm, Aliment. Pharmacol. Ther. 2002, 16, 343. dot: 10.1046/.T. 1365-2036.2002.01185.X
5. I. M. Coupar, P. V. Desmond, H. R. Irving, Curt: Neuropharmacol. 2007, 5, 224. doi:10.2174/157015907782793621
6. M. Langlois, R. Fisehmeister, J. Med. Chem. 2003, 46, 319. doi:10.1021/.JM020099F
7. A. Lochead, S. Jegham, F. Galli, A. Nedelec, T. Gallet, J. F. Jeunesse, Preparation of 1,4-diazabicyclo[2.2.2]oct-2-ylmethyl quinoline-8-earboxylates or - carboxamides as 5-HT4 agonists or antagonists and/or as 5-HT3 antagonists, French Patent 2756564 1998, pp. 16.
8. D. Marquess, P. R. Fatheree, S. D. Turner, D. D. Long, S.-K. Choi, A. A. Goldblum, D. Genov, Quinolinone-carboxamide compounds as 5-HT4 receptor agonists, US Patent 7,375,114 2008, pp. 31.
9. T. Kato, K. Kawamura, M. Morita, C. Uchida, Quinolonecarboxylic acid compounds, their preparation, pharmaceutical compositions, and 5-HT4 receptor agonistic activity, WO Patent 2005049608 2005, pp. 78.
10. C. C. Price, R. M. Roberts, J. Am. Chem. Soc. 1946, 68, 1204. doi:10.1021/JA01211A020
11. J. Mialet, Y. Dahmoune, F. Lezoualc'h, I. Berque-Bestel, P. Eftekhari, J. Hoebeke, S. Sicsic, M. Langlois, R. Fisehmeister, Br. J. Pharmacol. 2000, 130, 527. doi:10.1038/SJ.BJP0703356
12. L. Rivail, M. Giner, M. Gastineau, M. Berthouze, J. L. Soulier, R. Fisehmeister, F. Lezoualc'h, B. Maigret, S. Sicsic, I. Berque-Bestel, Br. J. Pharmacol. 2004, 143, 361. doi:10.1038/S.T.BJR0705950
13. L. Rivail, C. C. B. Maigret, I. Berque-Bestel, S. Sicsic, M. Tareg, Theochem. 2007, 817, 19. doi:10.1016/J.THEOCHEM.2007.04.012
14. J. D. Gale, C. J. Grossman, J. W. Whitehead, A. W. Oxford, K. T. Bunce, P. P. Humphrey, Br. J. Pharmacol. 1994, 111, 332.
15. K. Schofield, J. C. E. Simpson, J. Chem. Soc. 1946, 1033. doi: 10.1039/JR9460001033
16. E. H. Erickson, C. F. Hainline, L. S. Lenon, C. J. Matson, T. K. Rice, K. E. Swingle, M. Van Winkle, J. Med. Chem. 1979, 22, 816. doi:10.1021/JM00193A013
17. T. R. Bosin, M. G. Raymond, A. R. Buckpitt, Tetrahedron Lett. 1973, 14, 4699. doi:10.1016/S0040-4039(01)87313-5
18. W H. Guendel, S. Bohnert, Z. Naturforsch. B: Chem. Sci. 1988, 43, 769.
19. H. C. Brown, S. Narasimhan, Y. M. Choi, Synthesis 1980, 6, 441.