Radical scavenging by N-aminoazaaromatics

Bioorganic and Medicinal Chemistry

Volumn 8, Issue 8, 2000, Pages 1983-1989

  Itoh, Takashi ^a   Miyazaki, Michiko ^a   Maeta, Hiromi ^a   Matsuya, Yûji ^a   Nagata, Kazuhiro ^a   Ohsawa, Akio ^a  

^a SHOWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

N AMINOAZAAROMATIC DERIVATIVE; NITRIC OXIDE; NITROGEN OXIDE; OXYGEN; RADICAL; SCAVENGER; SUPEROXIDE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DEAMINATION; NONHUMAN; OXIDATION; STOICHIOMETRY;

AZA COMPOUNDS; HYDROCARBONS; MOLECULAR STRUCTURE; NITRIC OXIDE; OXYGEN; SUPEROXIDES;

EID: 0033859140     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(00)00118-8     Document Type: Article

References (36)

1. Methods in Nitric Oxide Research; Feelisch, M.; Stamler, J. S., Eds.; John Wiley & Sons, Chichester, 1996.
2. Pfeiffer S., Mayer B., Hemmens B. Angew. Chem., Int. Ed. Engl. 38:1999;1714. , and references cited therein.
3. Wink D.A., Mitchell J.B. Free Radical Biol. Med. 25:1998;434. , and references cited therein.
4. Hughes M.N. Biochim. Biophys. Acta. 1411:1999;263. , and references cited therein.
5. Schneider J.L., Carrier S.M., Ruggiero C.E., Young V.G. Jr., Tolman W.B. J. Am. Chem. Soc. 120:1998;11408.
6. Franz K.J., Lippard S.J. J. Am. Chem. Soc. 121:1999;10504.
7. Itoh T., Nagata K., Matsuya Y., Miyazaki M., Ohsawa A. J. Org. Chem. 62:1997;3582.
8. Itoh T., Matsuya Y., Nagata K., Ohsawa A. Tetrahedron Lett. 38:1997;4117.
9. Itoh T., Nagata K., Matsuya Y., Miyazaki M., Ohsawa A. Tetrahedron Lett. 38:1997;5017.
10. Matsuya Y., Itoh T., Nagata K., Ohsawa A. Tetrahedron. 53:1997;15701.
11. Itoh T., Matsuya Y., Maeta H., Miyazaki M., Nagata K., Ohsawa A. Chem. Pharm. Bull. 47:1999;133.
12. Itoh T., Matsuya Y., Maeta H., Miyazaki M., Nagata K., Ohsawa A. Chem. Pharm. Bull. 47:1999;819.
13. Hirobe et al. reported that N-aminopyridinium salts were deaminated by the reaction with nitrous acid in water; see, Okamoto, T.; Hirobe, M. Yuki Gosei Kagaku Kyokaishi 1968, 26, 746.
14. Hirobe et al. reported that N-aminopyridinium salts were deaminated by the reaction with nitrous acid in water; see, Okamoto, T.; Hirobe, M. Yuki Gosei Kagaku Kyokaishi 1968, 26, 746.
15. Palmer R.M.J., Ashton D.S., Moncada S. Nature. 333:1998;664.
16. Moro M.A., Darley-Usmar V.M., Goodwin D.A., Read N.G., Zamora-Pino R., Feelisch M., Radomski M.W., Moncada S. Proc. Natl. Acad. Sci. USA. 91:1994;6702.
17. Afanas'ev I.B. Superoxide Ion: Chemistry and Biological Implication. 1991;CRC, Boca Raton. Vol. 2.
18. Ohsawa A., Arai H., Ohnishi H., Itoh T., Kaihoh T., Okada M., Igeta H. J. Org. Chem. 50:1985;5520.
19. Beckman, J. S. In Nitric Oxide. Principles and Actions; Lancaster, J., Jr., Ed.; Academic, New York, 1994, pp. 1-82.
20. Green L.C., Wagner D.A., Glogowski J., Skipper P.L., Wishnok J.S., Tannenbaum S.R. Anal. Biochem. 126:1982;131.
21. Saito G., Sugimoto K., Hagino K. Bunseki Kagaku. 20:1971;542.
22. There are some papers which claim the reactions with superoxide were initialized by deprotonation from N-H bonds; see, (a) Crank, G.; Makin, M. I. H. Tetrahedron Lett. 1979, 20, 2169.
23. (b) Stuehr, D. J.; Marletta, M. A. J. Org. Chem. 1985, 50, 694.
24. Bielski B.H.J., Allen A.O. J. Phys. Chem. 81:1977;1048.
25. Lucas L.T., Gatehouse D., Shuker D.E.G. J. Biol. Chem. 274:1999;18319. , and references cited therein.
26. Bandish B.K., Shine H.J. J. Org. Chem. 42:1977;561.
27. Williams D.L.H. Nitrosation. 1998;Cambridge University Press, Cambridge. pp. 1-35.
28. Nitrosamines and Related N-Nitroso Compounds; Loeppky, R. N.; Michejda, C. J., Eds.; ACS Symposium Series 553, American Chemical Society, Washington, DC, 1994 and references cited therein.
29. Wolff D.J., Gribbin B.J. Arch. Biochem. Biophys. 311:1994;300. , and references cited therein.
30. Wolff D.J., Datto G.A., Samatovitz R.A., Tempsick R.A. J. Biol. Chem. 268:1993;9425.
31. Okamoto T., Hirobe M., Tamai Y., Yabe M. Chem. Pharm. Bull. 14:1966;506.
32. Okamoto T., Hirobe M., Yamazaki T. Chem. Pharm. Bull. 14:1966;512.
33. Tamura Y., Minamikawa J., Miki Y., Matsugashita S., Ikeda M. Tetrahedron. 29:1973;2359.
34. Adger, B. M.; Bradbury, S.; Keating, M.; Rees, C. W.; Storr, R. C.; Williams, M. T. J. Chem. Soc. Perkin Trans. 1 1975, 31.
35. Vinogradova O.V., Kryshtalyuk O.V., Rudnev M.I., Pozharskii A.F., Kuz'menko V.V. Chem. Heterocycl. Comp. 30:1994;1182.
36. Abramovitch, R. A.; Schofield, K. J. Chem. Soc. 1955, 2326.