Synthesis and pharmacological evaluation of 3-amino-1-(5-indanyloxy)-2- propanol derivatives as potent sodium channel blockers for the treatment of stroke

Chemical and Pharmaceutical Bulletin

Volumn 60, Issue 4, 2012, Pages 488-498

  Seki, Maki ^a   Tsuruta, Osamu ^a   Aoyama, Yukio ^a   Soejima, Aki ^a   Shimada, Hiroshi ^a   Nonaka, Hikaru ^a  

^a MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

Author keywords

Ischemic stroke; Neuroprotection; Neurotoxin receptor site 2; Sodium channel blocker

Indexed keywords

1 [4 (1H BENZIMIDAZOL 2 YL)PIPERIDIN 1 YL] 3 (2,3 DIHYDRO 1H INDEN 5 YLOXY)PROPAN 2 OL DIHYDROCHLORIDE; 3 AMINO 1 (5 INDANYLOXY) 2 PROPANOL; CROBENETINE; DOPAMINE 2 RECEPTOR; ENECADIN; NEUROTOXIN; SODIUM CHANNEL BLOCKING AGENT; SUN N 8075; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BRAIN ISCHEMIA; CONTROLLED STUDY; DEPOLARIZATION; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; MALE; MIDDLE CEREBRAL ARTERY OCCLUSION; NEUROPROTECTION; NONHUMAN; RAT; STROKE;

2-PROPANOL; ANIMALS; DISEASE MODELS, ANIMAL; INFARCTION, MIDDLE CEREBRAL ARTERY; MALE; MICROSOMES, LIVER; NEUROPROTECTIVE AGENTS; RATS; RATS, WISTAR; SODIUM CHANNEL BLOCKERS; STROKE;

EID: 84859461309     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.60.488     Document Type: Article

References (36)

1. Simon R. P., Swan J. H., Griffiths T., Meldrum B. S., Science, 226, 850-852 (1984).
2. Park C. K., Nehls D. G., Graham D. I., Teasdale G. M., McCulloch J., Ann. Neurol., 24, 543-551 (1988).
3. Carter C. J., Lloyd K. G., Zivkovic B., Scatton B., J. Pharmacol. Exp. Ther., 253, 475-482 (1990).
4. Sheardown M. J., Nielsen E. O., Hansen A. J., Jacobsen P., HonoréT., Science, 247, 571-574 (1990).
5. Takahashi M., Kohara A., Shishikura J., Kawasaki-Yatsugi S., Ni J. W., Yatsugi S., Sakamoto S., Okada M., Shimizu-Sasamata M., Yamaguchi T., CNS Drug Rev., 8, 337-352 (2002).
6. Zornow M. H., Prough D. S., New Horiz., 4, 107-114 (1996).
7. Taylor C. P., Meldrum B. S., Trends Pharmacol. Sci., 16, 309-316 (1995).
8. Urenjak J., Obrenovitch T. P., Pharmacol. Rev., 48, 21-67 (1996).
9. Hodgkin A. L., Huxley A. F., J. Physiol., 117, 500-544 (1952).
10. Catterall W. A., J. Biol. Chem., 252, 8669-8676 (1977).
11. Catterall W. A., Morrow C. S., Daly J. W., Brown G. B., J. Biol. Chem., 256, 8922-8927 (1981).
12. Albuquerque E. X., Daly J. W., Witkop B., Science, 172, 995-1002 (1971).
13. Catterall W. A., Annu. Rev. Pharmacol. Toxicol., 20, 15-43 (1980).
14. Deri Z., Adam-Vizi V., J. Neurochem., 61, 818-825 (1993).
15. Willow M., Catterall W. A., Mol. Pharmacol., 22, 627-635 (1982).
16. Matsuki N., Quandt F. N., Ten Eick R. E., Yeh J. Z., J. Pharmacol. Exp. Ther., 228, 523-530 (1984).
17. Kuo C. C., Bean B. P., Mol. Pharmacol., 46, 716-725 (1994).
18. Hille B., J. Gen. Physiol., 69, 497-515 (1977).
19. Löscher W., Wlaź P., Szabo L., Neurosci. Lett., 240, 33-36 (1998).
20. Shimidzu T., Itou Y., Tatsumi S., Hayashi S., Ukai Y., Yoshikuni Y., Kimura K., Naunyn Schmiedebergs Arch. Pharmacol., 355, 601-608 (1997).
21. Carter A. J., Grauert M., Pschorn U., Bechtel W. D., Bartmann-Lindholm C., Qu Y., Scheuer T., Catterall W. A., Weiser T., Proc. Natl. Acad. Sci. U.S.A., 97, 4944-4949 (2000).
22. Kotani Y., Morimoto N., Oida Y., Tamura Y., Tamura S., Inoue T., Shimazawa M., Yoshimura S., Iwama T., Hara H., Neuroscience, 149, 779-788 (2007).
23. Annoura H., Nakanishi K., Toba T., Takemoto N., Imajo S., Miyajima A., Tamura-Horikawa Y., Tamura S., J. Med. Chem., 43, 3372-3376 (2000).
24. Montastruc J. L., Llau M. E., Rascol O., Senard J. M., Fundam. Clin. Pharmacol., 8, 293-306 (1994).
25. Annoura H., Nakanishi K., Uesugi M., Fukunaga A., Imajo S., Miyajima A., Tamura-Horikawa Y., Tamura S., Bioorg. Med. Chem., 10, 371-383 (2002).
26. Miyaura N., Suzuki A., Chem. Rev., 95, 2457-2483 (1995).
27. Suzuki A., J. Organomet. Chem., 576, 147-168 (1999).
28. Kubota H., Fujii M., Ikeda K., Takeuchi M., Shibanuma T., Isomura Y., Chem. Pharm. Bull., 46, 351-354 (1998).
29. Wovkulich P. M., Uskoković M. R., Tetrahedron, 41, 3455-3462 (1985).
30. Liang G. B., Qian X., Bioorg. Med. Chem. Lett., 9, 2101-2104 (1999).
31. Kelarev V. I., Shvekhgeimer G. A., Chem. Heterocycl. Compd., 16, 501-506 (1980).
32. Aiuchi T., Daimatsu T., Nakaya K., Nakamura Y., Biochim. Biophys. Acta, 685, 289-296 (1982).
33. Zhang A., Neumeyer J. L., Baldessarini R. J., Chem. Rev., 107, 274-302 (2007).
34. van de Waterbeemd H., Camenisch G., Folkers G., Chretien J. R., Raevsky O. A., J. Drug Target., 6, 151-165 (1998).
35. Koizumi J., Yoshida Y., Nakazawa T., Ooneda G., Jpn. J. Stroke, 8, 1-8 (1986).
36. Bederson J. B., Pitts L. H., Germano S. M., Nishimura M. C., Davis R. L., Bartkowski H. M., Stroke, 17, 1304-1308 (1986).