Quantitative structure-activity analyses of novel hydroxyphenylurea derivatives as antioxidants

Bioorganic and Medicinal Chemistry

Volumn 6, Issue 6, 1998, Pages 849-868

  Nakao, Kazuya ^a   Shimizu, Ryo ^a   Kubota, Hitoshi ^a   Yasuhara, Mikiko ^a   Hashimura, Yoshimasa ^a   Suzuki, Toshikazu ^a   Fujita, Toshio ^b   Ohmizu, Hiroshi ^a  

^a MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Antioxidant; Hydroxyphenylurea; QSAR; Quantitative structure activity relationship

Indexed keywords

ANTIOXIDANT; CARBANILAMIDE DERIVATIVE;

ANTIOXIDANT ACTIVITY; ARTICLE; DRUG SYNTHESIS; LIPID PEROXIDATION; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIOXIDANTS; BRAIN; DRUG DESIGN; LIPID PEROXIDATION; MALE; MOLECULAR CONFORMATION; PHENYLUREA COMPOUNDS; QUANTUM THEORY; RATS; RATS, SPRAGUE-DAWLEY; REGRESSION ANALYSIS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0031833085     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(98)00039-X     Document Type: Article

References (28)

1. Halliwell, B. Drugs 1991, 42, 569-605.
2. Carew, T. E.; Schwenke, D. C.; Steinberg, D. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 7725-7729.
3. Niki, E.; Saito, T.; Kawakami, A.; Kamiya, Y. J. Biol. Chem. 1984, 259, 4177-4182.
4. Simic, M. G.; Jovanovic, S. V. J. Am. Chem. Soc. 1989, 111, 5778-5782.
5. Hansch, C.; Zhang, L. SAR QSAR Environ. Res. 1995, 4(2-3), 73-82.
6. Hansch, C.; Gao, H. Chem. Rev. 1997, 97, 2995-3059.
7. Brown, H. C.; Okamoto, Y. J. Am. Chem. Soc. 1958, 80, 4979-4987.
8. Exner, O. In Correlation Analysis in Chemistry; Chapman, N. B.; Shorter, J. editors. Plenum Press; New York, 1978, pp 439-540.
9. Fujita, T.; Nishioka, T. Prog. Phys. Org. Chem., 1976, 12, 49-89.
10. Sotomatsu, T.; Fujita, T. J. Org. Chem. 1989, 54, 4443-4448.
11. Nakagawa, Y.; Izumi, K.; Oikawa, N.; Sotomatsu, T.; Shigemura, M.; Fujita, T. Environ. Toxicol. Chem. 1992, 11, 901-916.
12. dCalculated by CLOGP method.
13. Hansch, C.; Leo, A.; Hoekman, D. Exploring QSAR; American Chemical Society: Washington, DC, 1995.
14. Leo, A. J. Chem. Rev. 1993, 93, 1281-1306.
15. ClogP for Macintosh, version 1.0.0, BioByte Corp. 201 W. Fourth St., Suite #204, Claremont, CA 91711 U.S.A.
16. Asao, M.; Nakao, K.; Shimizu, R.; Nishioka, T.; Fujita, T. submitted to Japan Chemistry Program Exchange (http:// jcpe.chem.ocha.ac.jp/).
17. Fujita, T. Prog. Phys. Org. Chem. 1983, 14, 75-113.
18. Allen, F. H.; Kennard, O. Chemical Design Automation News, 1993, 8(1), 1 & 31-37. The crystal structure data of 24 has been deposited to the Cambridge Crystallographic Data Center (http://www.ccdc.cam.ac.uk).
19. Burton, G. W.; Le Page, Y.; Gabe, E. J.; Ingold, K. U. J. Am. Chem. Soc. 1980, 102(26), 7791-7792.
20. Gerber, J. J.; Caira, M. R.; Lotter, A. P. J. Crystallogr. Spectrosc. Res. 1993, 23(11), 863-869.
21. Wavefunction, Inc. 18401 Von Karman Ave., #370, Irvine, CA 92715 U.S.A.
22. Nakayama, A.; Hagiwara, K.; Hashimoto, S.; Shimoda, S. Quant. Struct.-Act. Relat. 1993, 12, 251-255.
23. Fukui, K.; Nagata, C.; Yonezawa, T. J. Am. Chem. Soc. 1958, 80, 2267-2270.
24. Yukawa, Y.; Tsuno, Y. Bull. Chem. Soc. Japan 1959, 32, 971.
25. Howard, J. A.; Ingold, K. U. Can. J. Chem. 1963, 41, 2800-2806.
26. Das, P. K.; Encinas, M. V.; Steenken, S.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 4162-4166.
27. Yasuhara, M.; Saito, K.; Kubota, H.; Ohmizu, H.; Suzuki, T. Biol. Pharm. Bull. 1997, 20, 1056-1060.
28. Ohkawa, H.; Ohishi, N.; Yagi, K. Anal. Biochem. 1979, 95, 351-358.