Synthesis of 4-phenylamino-3-vinylquinoline derivatives as gastric H +/K+-ATPase inhibitors

Bulletin of the Korean Chemical Society

Volumn 25, Issue 7, 2004, Pages 1091-1094

  Eul, Kgun Yum ^a   Yang, Ok Kyung ^a   Seung, Kyu Kang ^b   Hyae, Gyeong Cheon ^b   Sung, Soo Kim ^b   Choi, Joong Kwon ^b  

^a Chungnam National University   (South Korea)

^b Korea Research Institute of Chemical Technology   (South Korea)

Author keywords

3 Vinylquinoline; Gastric H+ K + ATPase; Heck reaction; Palladium

Indexed keywords

3 (2 ETHOXYCARBONYL 1 ETHENYL) 8 METHOXY 4 (2 METHYLPHENYLAMINOQUINOLINE); 3 IODO 4 (2 METHYLPHENYLAMINO) 8 METHOXYQUINOLINE; 4 CHLORO 3 IODO 8 METHOXYQUINOLINE; 8 HYDROXY 4 (2 METHYLPHENYLAMINO) 3 (3 PHENYLAMINO 1 PROPENYLQUINOLINE); 8 METHOXY 4 (2 METHYLPHENYLAMINO) 3 (3 PHENYLAMINO 1 PROPENYLQUINOLINE); PROTON PUMP INHIBITOR; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; HECK REACTION; IC 50; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 5344222697     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2004.25.7.1091     Document Type: Article

References (29)

1. Pope, A. J.; Parsons, M. E. Trends Pharmacol. Sci. 1993, 14, 323.
2. Kaminski, J. J.; Bristol, J. A.; Puchalski, C.; Lovey, R. G.; Elliot, A. J.; Guzik, H.; Solomon, D. M.; Conn, J. D.; Domalski, M. S.; Wong, S.-C.; Gold, E. H.; Long, J. F.; Chiu, P. J.; Steinberg, M.; Mcphail, A. T. J. Med. Chem. 1985, 28, 876.
3. Leach, C. A.; Brown, T. H.; Ife, R. J.; Keeling, D. J.; Parsons, M. E.; Price, C. A.; Wiggall, K. J. J. Med. Chem. 1992, 35, 1845.
4. Ife, R. J.; Brown, T. H.; Keeling, D. J.; Leach, C. A.; Meeson, M. L.; Parsons, M. E.; Reavil, D. R.; Theobald, C. J.; Wiggal, K. J. J. Med. Chem. 1992, 35, 3413.
5. Leach, C. A.; Brown, T. H.; Ife, R. J.; Keeling, D. J.; Parsons, M. E.; Theobald, C. J.; Wiggall, K. J. J. Med. Chem. 1995, 38, 2748.
6. Ife, R. J.; Brown, T. H.; Blurto, P.; Keeling, D. J.; Leach, C. A.; Meeson, M. L.; Parsons, M. E.; Theobald, C. J. J. Med. Chem. 1995, 38, 2763.
7. Han, K. S.; Kim, Y. G.; Yoo, K. K.; Lee, J. W.; Lee, M. G. Biopharm. Drug Dis. 1998, 19, 493.
8. Pope, A. J.; Boehm, M. K.; Leach, C.; Ife, R. J.; Keeling, D.; Parsons, M. E. Bioch. Pharm. 1995, 50, 1543.
9. Parson, M. E.; Rushant, B.; Rasmussen, T. C.; Leach, C.; Ife, R. J.; Postius, S.; Pope, A. J. Bio. Pharm. 1995, 50, 1551.
10. Cheon, H. G.; Kim, H. J.; Mo, H. K.; Lee, B. H.; Choi, J.-K. Pharmacology 2000, 60, 161.
11. Cheon, H. G.; Lim, H.; Lee, D.-H. Eur. J. Pharm. 2001, 411, 181.
12. Yum, E. K.; Kang, S. K.; Kim, S. S.; Choi, J.-K.; Cheon, H. G. Bioorg. Med. Chem. Lett. 1999, 9, 2819.
13. (a) Cheon, H. G.; Yum, E. K.; Kim, S. S. Arch. Pharm. Res. 1996, 19, 126.
14. (b) Cheon, H.-G.; Kim, H. J.; Yum, E. K.; Cho, S. Y.; Kim, D. Y.; Yang, S. I. J. Appl. Pharm. 1995, 3, 205.
15. Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; A Guide for the Synthetic Chemist; Pregamon: 2000.
16. (a) Tsuji, J. Palladium Reagents and Catalysts; Wiley: 1995.
17. (b) Negishi, E. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley-Interscience: 2002; Vol. 2, pp 1669-2117.
18. (c) Trost, B. M.; Fleming, I. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 4, pp 585-661.
19. Renault, J.; Malliet, P.; Renault, S.; Berlot, J. Synthesis 1977, 865.
20. (a) Park, S. S.; Choi, J.-K.; Yum, E. K.; Ha, D.-C. Tetrahedron Lett. 1998, 39, 627.
21. (b) Chi, S. M.; Choi, J.-K.; Yum, E. K.; Chi, D. Y. Tetrahedron. Lett. 2000, 41, 919.
22. (c) Lee, M. S.; Yum, E. K. Bull. Korean Chem. Soc. 2002, 23, 535.
23. (d) Kang, S. S.; Yum, E. K.; Sung, N.-D. Heterocycles 2003, 60, 2727.
24. (e) Hong, K. B.; Lee, C. W.; Yum, E. K. Tetrahedron Lett. 2004, 45, 636.
25. (a) Kang, S. K.; Park, S. S.; Kim, S. S.; Choi, J.-K.; Yum, E. K. Tetrahedron Lett. 1999, 40, 4379.
26. (b) Gee, M. B.; Lee, W. J.; Yum, E. K. Bull. Korean Chem. Soc. 2003, 24, 1381.
27. (c) Lee, W. J.; Gee, M. B.; Yum, E. K. Heterocycles 2003, 60, 1821.
28. Bradford, M. M. Anal. Biochem. 1976, 72, 248.
29. Yoda, A.; Hokin, L. E. Biochem. Biophys. Res. Commun. 1970, 40, 880.