Functionalized N-Hydroxyamide-Containing Heterocycles-Synthesis, Reaction, and Metal-Chelating Property

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 55, Issue 6, 1997, Pages 524-534

  Ohkanda, Junko ^a   Katoh, Akira ^a  

^a SEIKEI UNIVERSITY   (Japan)

Author keywords

2(1h) pyrimidinone; 21h pyrazinone; Acylating agent; Amino acid; Iron complex; N hydroxyamide containing heterocycles; Photoreaction; Ring transformation; Siderophore; Transferrin

Indexed keywords

EID: 1542469371     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.55.524     Document Type: Article

References (48)

1. (a) G. Winkelmann, D. van der Helm, J.B. Neilands, "Iron Trasport in Microbes, Plants and Animals", VCH, Weinheim, 1987;
2. (b) G. Winkelmann, "Handbook of Microbial Iron Chelates". CRC Press, Boca Raton, 1991;
3. (c) R.J. Bergeron, G.M. Brittenham, "The Development of Iron Chelators for Clinical Use", CRC Press, Boca Raton, 1992;
4. A. Katoh, J. Ohkanda, A. Tamura, Y. Yoshiike, K. Mitsuhashi, Heterocycles, 37, 1141 (1994)
5. J. Ohkanda, T. Kumasaka, A. Takasu, T. Hasegawa, A. Katoh, Heterocycles, 43, 883 (1996)
6. A. Katoh, J. Ohkanda, Y. Itoh, K. Mitsuhashi, Chem. Lett., 1992, 2009
7. A. Katoh, S. Kondoh, J. Ohkanda, Heterocyclic Commun., 2, 141 (1996)
8. J. Ohkanda, T. Tokumitsu, K. Mitsuhashi, A. Katoh, Bull. Chem. Soc. Jpn., 66, 841 (1993)
9. J. Ohkanda, A. Katoh, J. Org. Chem., 60, 1583 (1995)
10. J. Ohkanda, A. Katoh, Tetrahedron, 51, 12995 (1995)
11. J. Ohkanda, A. Katoh, Chem. Lett., 1996, 423
12. C. Kashima, A. Katoh, Y. Yokota, Y. Omote, Chem. Pharm. Bull., 29, 2516 (1981)
13. (a) E. Lipczynska-Kochany, "Some New Aspects of Hydroxamic Acids Chemistry", Prace Naukowe Politechniki Warszawskiej, Chem. 46, Warszawa, 1988;
14. (b) E. Lipczynska-Kochany, Chem. Rev., 91, 477 (1991)
15. (a) H. Furrer, Tetrahedron Lett., 1974, 2953;
16. (b) A.R. Katrizky, A.V. Chapman, M.J. Cook, G.H. Millet, J. Chem. Soc., Perkin Trans. 1, 1980, 2743;
17. (a) A.R. Katritzky, M.F. Gordeev, J. Chem. Soc., Perkin Trans. 1, 1991, 2199;
18. (b) A.I. Meyer, "Heterocycles in Organic Synthesis", Vol.3, John Wiley & Sons, New York, 1974
19. Y. Okuwaki, Y. Inagawa, H. Tamamura, T. Suzuki, H. Kuwana, M. Tahara, K. Yuasa, A. Ohta, J. Heterocycl. Chem., 24, 187 (1987)
20. D.H. Rich, J. Singh, "The Peptide", Vol.1, eds. by E. Gross, M. Meienhofer, Academic Press, New York, 1979, p. 242-262
21. (a) B. Weinstein, A.E. Prichard, J. Chem. Soc., Perkin Trans. 1, 1972, 1015;
22. (b) K. Kawasaki, T. Tsuji, K. Hirase, M. Miyano, Y. Imote, Chem. Pharm. Bull., 39, 583 (1991)
23. (a) R. Geiger, W. König, 'The Peptide", Vol. 3, eds. by E. Gross, J. Meienhofer, Academic Press, New York, 1981, p.1-88;
24. (b) T.W. Greene, P.G.M. Wuts, "Protective Groups in Organic Synthesis", John Wiley & Sons, New York, 1991
25. A. Ohta, Y. Inagawa, C. Mitsugi, J. Heterocycl. Chem., 22, 1643 (1985)
26. (a) N.F. Olivieri, D.M. Templeton, G. Koren, D. Chung, C. Hermann, M.H. Freedman, R.A. McClelland, Ann. N. Y. Acad. Sci., 612, 369 (1990);
27. (b) P. Tondury, G.J. Kontoghiorghes, A. Ridolfi-Luthy, A. Hirt, A.V. Hoffbrand, A.M. Lottenbach, T. Sonderegger, H.P. Wagner, Br. J. Haematol., 76, 550 (1990);
28. (c) F.N. Al-Refaie, B. Wonke, A. V. Hoffbrand, D. G. Wickens, P. Nortey, G.J. Kontoghiorghes, Blood, 80, 593 (1992)
29. (a) R.C. Scarrow, P.E. Riely, K. Abu-Dari, D.L. White, K.N. Raymond, Inorg. Chem., 24, 954 (1985);
30. (b) R.C. Scarrow, D.L. White, K,N. Raymond, J. Am. Chem. Soc., 107, 6540 (1985);
31. (c) R.C. Scarrow, K.N. Raymond, Inorg. Chem., 27, 4140 (1988);
32. (d) R.C. Hider, G.J. Kontoghiorghes, J. Silver, UKP, GB-2118176, (1982); B. Faller, H. Nick, J. Am. Chem. Soc., 116, 3860 (1994)
33. (d) R.C. Hider, G.J. Kontoghiorghes, J. Silver, UKP, GB-2118176, (1982); B. Faller, H. Nick, J. Am. Chem. Soc., 116, 3860 (1994)
34. (a) M. Streater, P.D. Taylor, R.C. Hider, J. Porter, J. Med. Chem., 33, 1749 (1990);
35. (b) A. E. Martell, R.J. Motekaitis, Y. Sun, E.T. Clarke, "The Development of Iron Chelators for Clinical Use", eds. by R.J. Bergeron, G.M. Brittenham, CRC Press, Boca Raton, 1992, p. 329
36. A. Katoh, Y. Hida, J. Ohkanda, J. Chem. Soc., Perkin Trans, 1
37. J. Ohkanda, J. Kamitani, T. Tokumitsu, Y. Hida, T. Konakahara, A. Katoh, J. Org. Chem., in press.
38. C.J. Carrano, K.N. Raymond, J. Am. Chem. Soc., 101, 5401 (1979)
39. G. Anderegg, F. L'Eplattenier, G. Schwarzenbach, Helv. Chim. Acta, 46, 1400 and 1409 (1963)
40. (a) D. van der Helm, J.R. Baker, D.L. Eng-Wilmont, M.B. Hossain, R.A. Loghry, J. Am. Chem. Soc., 102, 5371 (1980);
41. (b) C.J. Carrano, K.N. Raymond, J. Am. Chem. Soc., 100, 5371 (1978);
42. (c) K.N. Raymond, G. Muller, B.F. Matzanke, Top. Curr. Chem., 123, 49 (1984)
43. (a) K. Konopka, A. Bindereif, J.B. Neilands, Biochemistry, 21, 6503 (1982);
44. (b) R.E. Cowart, N. Kojima, G.W. Bates, J. Biol. Chem., 101, 5401 (1982);
45. (c) S.A. Kretchmar, A. Craig, K. N. Raymond, J. Am. Chem. Soc., 115, 6758 (1993)
46. J. Ohkanda, Doctor thesis, The University of Tokyo, 1996