Acyclic analogs of kainoids: Their syntheses and depolarizing activities

Tetrahedron

Volumn 52, Issue 6, 1996, Pages 1931-1942

  Hashimoto, Miwa ^a   Hashimoto, Kimiko ^a,b   Shirahama, Haruhisa ^a,b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLUTAMIC ACID DERIVATIVE;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; NEUROTOXICITY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; RAT; REACTION ANALYSIS; STEREOCHEMISTRY;

ANIMALIA;

EID: 0030041456     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01058-0     Document Type: Article

References (23)

1. (a)Kainic Acid as A Tool in Neurobiology; McGeer, E. G.; Olney, J. W.; McGeer, P. L. Eds; Raven Press: New York, 1978.
2. (b) Ishida, M.; Shinozaki, H. Br. J. Pharmacol. 1991, 104, 873-878.
3. Konno, K; Hashimoto, K.; Ohfune, Y.; Shirahama, H.; Matsumoto, T. J. Am. Chem. Soc. 1988, 110, 4807-4815.
4. Kwak, S.; Aizawa, H.; Ishida, M.; Shinozaki, H. Experimental Neurology 1992, 116, 145-155.
5. (a) Hashimoto, K.; Shirahama, H. :Syntheses of Neuroexcitatory Kainoids. In Trens in Organic Chemistry; Karma, V. Ed; Research Trends: Trivandrum India, 1991, pp. 1-32.
6. (b) Horikawa, M.; Shima, Y.; Hashimoto, K; Shirahama, H. Heterocycles 1995, 40, 1009-1014.
7. (c) Horikawa, M.; Hashimoto, K; Shirahama, H. Tetrahedron Lett. 1993, 34, 331-334.
8. (d) Konno, K; Hashimoto, K.; Shirahama, H. Heterocycles 1992, 33, 303-311.
9. (d) Hashimoto, K.; Shirahama, H Tetrahedron Lett. 1991, 32, 2625-2628.
10. (e) Hashimoto, K.; Horikawa, M.; Shirahama, H. Tetrahedron Lett. 1990, 31, 7047-7050.
11. (a) Hashimoto, K.; Horikawa, M.; Ishida, M.; Shinozaki, H.; Shirahama, H. Bioorg. Med. Chem. Lett. 1992, 2, 743-746.
12. (b) Hashimoto, K.; Ohfune, Y.; Shirahama, H. Tetrahedron Lett. 1995, 36, 6235-6238.
13. This work was reported in preliminary form: Yanagida, M.; Hashimoto, K.; Ishida, M.; Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799-3802. β-Benzyl-and β-butenylglutamic acids were synthesized by other groups through different routes after communication of our work.: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C-G.; Boulanger, T.; Norberg, B.; Eunard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729-5733.
14. This work was reported in preliminary form: Yanagida, M.; Hashimoto, K.; Ishida, M.; Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799-3802. β-Benzyl-and β-butenylglutamic acids were synthesized by other groups through different routes after communication of our work.: (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C-G.; Boulanger, T.; Norberg, B.; Eunard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729-5733.
15. (b) Suzuki, K.; Seebach, D. Liebig's Ann. Chem. 1992, 51-61.
16. Garner P., Tetrahedron Lett. 1984, 25, 5855-5858.
17. Still W. C.; Gennari, C., Tetrahedron Lett. 1983 24, 4405-4408.
18. Sakai, N.; Ohfune, Y. J. Am. Chem. Soc. 1992, 114, 998-1010.
19. This compound was also synthesized by other groups through different methods.: (a) Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y. J. Org. Chem. 1991, 56, 4167-4176.
20. (b) Yoda, H.; Naito, S.; Takabe, K.; Tanaka, N.; Hosoya, K. Tetrahedron Lett. 1990, 31, 7623-7626.
21. Experimental procedure to measure depolarizing activity: Ishida, M.; Shinozaki, H. Br. J. Pharmacol. 1991, 104, 873-978.
22. Dihydrokainic acid has been previously found to have almost no activity.: Slevin, J. L. Brain Res. 1983, 265, 169-172.
23. Shinozaki, H.: Kainic acid receptor agonists. In Excitatory Amino Acid Receptors, Krogsgaard-Larsen, P.; Hansen, J. J. Eds; Ellis Horwood: New York, 1992, pp261-291.