Preparation and pharmacological evaluation of 1-(1,4-benzoquinon-2-yl)-1,2,3,4-tetrahydronaphthalenes as potent cerebral protective agents

Chemical and Pharmaceutical Bulletin

Volumn 44, Issue 1, 1996, Pages 132-138

  Suzuki, Kenji ^a   Tatsuoka, Toshio ^a   Ishihara, Takafumi ^a   Ohno, Tomochika ^a   Aisaka, Kazuo ^a   Ogino, Ryoko ^a   Kuroki, Manami ^a   Satoh, Fumio ^a   Miyano, Seiji ^b   Sumoto, Kunihiro ^b  

^a SUNTORY LTD   (Japan)

^b FUKUOKA UNIVERSITY   (Japan)

Author keywords

1,4 benzoquinone; Anti lipid peroxidation activity; Cerebral protective agent; Hypobaric hypoxia; Tetrahydronaphthalene

Indexed keywords

1 (5,6 DIMETHOXY 3 METHYL 1,4 BENZOQUINON 2 YL) 1,2,3,4 TETRAHYDRO 2 NAPHTHALENEACETAMIDE; 1 (5,6 DIMETHOXY 3 METHYL 1,4 BENZOQUINON 2 YL) 1,2,3,4 TETRAHYDRONAPHTHALENE 3 CARBOXYLIC ACID; ANTIINFLAMMATORY AGENT; SUN 4757; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIINFLAMMATORY ACTIVITY; ARTICLE; BRAIN HYPOXIA; BRAIN PROTECTION; DRUG CONFORMATION; DRUG EFFECT; DRUG SYNTHESIS; HYPOBARISM; INTRAPERITONEAL DRUG ADMINISTRATION; LIPID PEROXIDATION; MOUSE; NONHUMAN; ORAL DRUG ADMINISTRATION; STRUCTURE ACTIVITY RELATION;

ANIMALS; BENZOQUINONES; BRAIN ISCHEMIA; CEREBROVASCULAR CIRCULATION; MALE; MICE; NEUROPROTECTIVE AGENTS; RATS; RATS, WISTAR; TETRAHYDRONAPHTHALENES;

EID: 0030061590     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.132     Document Type: Article

References (19)

1. Series on studies of cerebral protective agents. a) Miyano S., Tatsuoka T., Suzuki K., Imao K., Satoh F., Ishihara T , Hirotsu I., Kihara T., Hatta M., Horikawa Y., Sumoto K., Chem. Pharm. Bull., 38, 1570 (1990); b) Tatsuoka T., Imao K., Suzuki K., Shibata M., Satoh F , Miyano S., Sumoto K., Heterocycles, 30, 749 (1990); c) Tatsuoka T., Suzuki K., Imao K., Satoh F., Ishihara T., Hirotsu I., Kihara T., Hatta M., Horikawa Y., Sumoto K., Miyano S., Chem. Pharm. Bull., 40, 2382 (1992)
2. Series on studies of cerebral protective agents. a) Miyano S., Tatsuoka T., Suzuki K., Imao K., Satoh F., Ishihara T , Hirotsu I., Kihara T., Hatta M., Horikawa Y., Sumoto K., Chem. Pharm. Bull., 38, 1570 (1990); b) Tatsuoka T., Imao K., Suzuki K., Shibata M., Satoh F , Miyano S., Sumoto K., Heterocycles, 30, 749 (1990); c) Tatsuoka T., Suzuki K., Imao K., Satoh F., Ishihara T., Hirotsu I., Kihara T., Hatta M., Horikawa Y., Sumoto K., Miyano S., Chem. Pharm. Bull., 40, 2382 (1992)
3. Series on studies of cerebral protective agents. a) Miyano S., Tatsuoka T., Suzuki K., Imao K., Satoh F., Ishihara T , Hirotsu I., Kihara T., Hatta M., Horikawa Y., Sumoto K., Chem. Pharm. Bull., 38, 1570 (1990); b) Tatsuoka T., Imao K., Suzuki K., Shibata M., Satoh F , Miyano S., Sumoto K., Heterocycles, 30, 749 (1990); c) Tatsuoka T., Suzuki K., Imao K., Satoh F., Ishihara T., Hirotsu I., Kihara T., Hatta M., Horikawa Y., Sumoto K., Miyano S., Chem. Pharm. Bull., 40, 2382 (1992)
4. a) Safar P., Bleyaert P., Nemoto E. M., "Brain Heart Infarct II," Springier Verlag, New York, 1977, p. 251;
5. b) Smith A. L., Hof J. T., Nielsen S. L , Larson C. P., Stroke, 5, 1 (1974);
6. c) Yasuda H., Shuto S., Tsugami T., Nakajima A , Arch. Int. Pharmacodyn., 233, 133 (1973).
7. a) Giannota S. L., Weiss M. H., Apuzzo M. L. J., Neurosurgury, 15, 497 (1984);
8. b) Hashi K., Takakura K., Sano K., No To Sinkei, 40, 373 (1988).
9. a) Braughler J. M., Hall E. D., Free Radical Med., 6, 289 (1989);
10. b) Zweier J. L., Kuppusamy P., Lutty G. A., Proc Natl. Acad. Sci. U.S A., 85, 4046 (1988)
11. Mccord J. M., Fridovich I., J. Biol. Chem., 244, 6049 (1969).
12. a) Jacobsen E. J., MacCall J. M., Ayer D. E., VanDoornick F. J., Palmer J. R., Belonga K. L., Braughler J. M., Hall E. D., Hauser D. J., Krook M. A., Runge T. A., J Med. Chem., 33, 1145 (1990);
13. b) Oshiro Y., Sakurai Y., Tanaka T., Ueda H., Kikuchi T., Tottori K., ibid., 34, 2004 (1991).
14. Chatterjee A., Banerjee D., Banerjee S., Tetrahedron Lett., 1965, 3851.
15. α radiation (λ=1.5418 Å). The structure was solved by the direct method, and refined by a block-diagonal least-squares method. The final R value was 0.103 for 6503 uique reflections.
16. a) Lawlor J. M., McNamee M. B., Tetrahedron Lett., 24, 2211 (1983);
17. b) Stevens D. R., Whiting D. A., ibid., 27, 4629 (1986).
18. Stocks J., Gutteridge J. M. C , Sharp R. J., Dormandy T. L., Clin. Sci. Mol. Med., 47, 215 (1974).
19. Nakanishi M., Yasuda Y , Tsumagari T., Life Sci., 13, 467 (1973).