Synthesis of azine-type heterocyclic compounds and their conversion into functional molecules

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 62, Issue 4, 2004, Pages 335-346

  Katoh, Akira ^a   Saito, Ryota ^b  

^a SEIKEI UNIVERSITY   (Japan)

^b NONE

Author keywords

6 aminoquinoxaline; Allosteric binding; Fluorescent chiral derivatization reagent; Growth promotion activity; Hexapeptide; Insulin mimetic activity; Iron(III) complex; Oxovanadium complex; Zinc(II) complex

Indexed keywords

AMINO ACIDS; CYCLIC VOLTAMMETRY; ELECTRON SPIN RESONANCE SPECTROSCOPY; INFRARED SPECTROSCOPY; INSULIN; IRON COMPOUNDS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEINS; SYNTHESIS (CHEMICAL); ULTRAVIOLET SPECTROSCOPY;

6-AMINOQUINOXALINE; ALLOSTERIC BINDING; FLUORESCENT CHIRAL DERIVATIZATION REAGENTS; HEXAPEPTIDES; INSULIN-MIMETIC ACTIVITY; OXOVANADIUM COMPOUNDS;

AROMATIC COMPOUNDS;

EID: 2942650998     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.62.335     Document Type: Review

References (91)

1. Y. Ohkura, Adv. Chromatogr., 29, 221 (1989)
2. M. Yamaguchi, Dojin News, No. 68, 10 (1993)
3. Y. Ohkura, H. Kai, H. Nohta, Bunseki Kagaku, 43, 259 (1994)
4. K. Iwaki, T. Bunrin, Y. Kameda, M. Yamazaki, J. Chromatogr., A, 662, 87 (1994)
5. J. Kondo, T. Imaoka, T. Kawasaki, A. Nakanishi, Y. Kawahara, J. Chromatogr., 645, 75 (1993)
6. J. Goto, M. Ito, S. Katsuki, N. Saito, T. Nambara, J. Liq. Chromatogr., 9, 683 (1986)
7. Y. Nishida, E. Itoh, M. Abe, H. Ohrui, H. Meguro, Anal. Sci., 11, 213 (1995)
8. J. Gal, A. J. Sedman, J. Chromatogr., 314, 275 (1984)
9. T. Kinoshita, Y. Kasahara, N. Nimura, J. Chromatogr., 210, 77 (1981)
10. Y. Yasaka, T. Matsumoto, M. Tanaka, Anal. Sci., 11, 295 (1995)
11. S. Einarsson, B. Josefsson, P. Moller, D. Sanchez, Anal. Chem., 59, 1191 (1987)
12. H. Spahn, D. Krauß, E. Mutschler, Pharm. Res., 5, 107 (1988); H. Spahn, P. Langguth, ibid., 7, 1262 (1990)
13. H. Spahn, D. Krauß, E. Mutschler, Pharm. Res., 5, 107 (1988); H. Spahn, P. Langguth, ibid., 7, 1262 (1990)
14. N. Nimura, T. Kinoshita, J. Chromatogr., 352, 169 (1986)
15. R. H. Buck, K. Krummen, J. Chromatogr., 387, 255 (1987)
16. F. J. Belas, M. A. Phillips, N. R. Srinivas, R. H. Barbhaiya, I. A. Blair, Biomed. Chromatogr., 9, 140 (1995)
17. C. Vogt, A. Georgi, G. Werner, Chromatographia, 40, 287 (1995)
18. T. Toyo'oka, Yi-Ming Liu, J. Chromatogr. A, 689, 23 (1995)
19. K. Akasaka, H. Meguro, H. Ohrui, Tetrahedron Lett., 38, 6853 (1997)
20. A. Katoh, M. Takahashi, J. Ohkanda, Chem. Lett., 1996, 369
21. A. Katoh, T. Fujimoto, M. Takahashi, J. Ohkanda, Heterocycles, 50, 299 (1999); A. Katoh, T. Yoshida, J. Ohkanda, ibid., 52, 911 (2000)
22. A. Katoh, T. Fujimoto, M. Takahashi, J. Ohkanda, Heterocycles, 50, 299 (1999); A. Katoh, T. Yoshida, J. Ohkanda, ibid., 52, 911 (2000)
23. H. D. Durst, M. Milano, Anal. Chem., 47, 1797 (1975)
24. T. Mukaiyama, R. Matsueda, M. Suzuki, Tetrahedron Lett., 1970, 1901
25. M. F. Perutz, "Mechanisms of Cooperativity and Allosteric Regulation in Proteins" Cambridge University Press, Cambridge, 1989
26. E. E. Kim, H. W. Wyckoff, J. Mol. Biol., 218, 449 (1991); I. O. Fritsky, R. Ott, R. Kramer, Angew. Chem. Int. Ed., 39, 3255 (2000)
27. E. E. Kim, H. W. Wyckoff, J. Mol. Biol., 218, 449 (1991); I. O. Fritsky, R. Ott, R. Kramer, Angew. Chem. Int. Ed., 39, 3255 (2000)
28. T. Nabeshima, Coord. Chem. Rev., 148, 151 (1996)
29. T. Nabeshima, T. Inaba, T. Sagae, N. Furukawa, Tetraheron Lett., 31, 3919 (1990)
30. E. Graf, M. W. Hosseini, R. Ruppert, N. Kyristakas, A. D. Cian, J. Fischer, C. Estournes, F. Taulelle, Angew. Chem., Int. Ed. Engl., 34, 1115 (1995)
31. R. W. Saalfrank, A. Dresel, V. Seitz, S. Trummer, F. Hampel, M. Teichert, O. Stalke, C. Stadler, J. Daub, V. Schunemann, A. X. Trautwein, Chem. Eur. J., 3, 2058 (1997)
32. M. Albrecht, S. Kotila, Chem. Commun., 1996, 2309; M. Albrecht Chem. Eur. J., 3, 1466 (1997)
33. M. Albrecht, S. Kotila, Chem. Commun., 1996, 2309; M. Albrecht Chem. Eur. J., 3, 1466 (1997)
34. M. Albrecht, O. Blau, Chem. Commun., 1997, 345
35. T. Nabeshima, Y. Yoshihira, T. Saiki, S. Akine, E. Horn, J. Am. Chem. Soc., 125, 28 (2003)
36. J. Ohkanda, A. Katoh, Rev. Heteroatom Chem., 18, 87 (1998)
37. J. Ohkanda, H. Shibui, A. Katoh, J. Inorg. Biochem., 67, 448 (1997); idem, Chem. Commun., 1998, 375
38. J. Ohkanda, H. Shibui, A. Katoh, J. Inorg. Biochem., 67, 448 (1997); idem, Chem. Commun., 1998, 375
39. A. Katoh, H. Kudo, R. Saito, J. Supramol. Chem., 2, 79 (2002)
40. J. Ohkanda, A. Katoh, Tetrahedron, 51, 12995 (1995)
41. M. Llinas, P. M. Klein, J. B. Neilands, J. Mol. Biol., 52, 399 (1970)
42. H. Benesi, J. H. Hildebrand, J. Am. Chem. Soc., 71, 2703 (1949); Y. Aoyama, M. Asakawa, Y. Matsui, H. Ogoshi, ibid., 113, 6233 (1991)
43. H. Benesi, J. H. Hildebrand, J. Am. Chem. Soc., 71, 2703 (1949); Y. Aoyama, M. Asakawa, Y. Matsui, H. Ogoshi, ibid., 113, 6233 (1991)
44. G. Winkelman, D. van der Helm, J. B. Neilands, "Iron Transport in Microbes, Plants and Animals", VCH, Weinheim, 1987
45. W. Kaim, B. Schwederski, "Bioinorganic Chemistry: Inorganic Elements in the Chemistry of Life", John Wiley & Sons, New York, 1991
46. G. Winkelmann, "Handbook of Microbial Iron Chelators", CRC Press, Boca Raton, 1991
47. G. Winkelmann, C. J. Carrano, "Transition Metals in Microbial Metabolism", Harwood Academic Publishers, United Kingdom, 1997
48. S. T. Callender, D. J. Weatherall, Lancet, 1980, 689; C. Kattamis, J. Fitsialos, C. Sinopoulou, Lancet, 1981, 51
49. S. T. Callender, D. J. Weatherall, Lancet, 1980, 689; C. Kattamis, J. Fitsialos, C. Sinopoulou, Lancet, 1981, 51
50. M. R. Summers, A. Jacobs, D. Tudway, P. Perera, C. Rickett, Br. J. Haematol., 42, 547 (1979)
51. M. J. Miller, F. Malouin, "The Development of Iron Chelators for Clinical Use" ed. by R. J. Bergeron, G. M. Brittenham, CRC Press, Boca Raton, 1992, p 277
52. A. Katoh, Y. Hikita, M. Harata, J. Ohkanda, T. Tsubomura, A. Higuchi, R. Saito, K. Harada, Heterocycles, 55, 2171 (2001)
53. A. Katoh, Y. Inoue, H. Nagashima, Y. Hikita, J. Ohkanda, R. Saito, Heterocycles, 58, 371 (2002)
54. R. C. Scarrow, P. E. Riley, K. Abu-Dari, D. L. White, K. N. Raymond, Inorg. Chem., 24, 954 (1985)
55. M. Akiyama, A. Katoh, M. Iijima, T. Takagi, K. Natori, T. Kojima, Bull. Chem. Soc. Jpn., 65, 1356 (1992)
56. P. S. Dobbin, R. C. Hider, A. D. Hall, P. D. Taylor, P. Sarpong, J. B. Poter, G. Xiao, D. van der Helm, J. Med. Chem., 36, 2448 (1993)
57. A. Shanzer, J. Libman, R. Lazar, Y. Tor, Pure Appl. Chem., 61, 1529 (1989)
58. J. Ohkanda, A. Katoh, J. Org. Chem., 60, 1583 (1995); idem, Chem. Lett., 1996, 423
59. J. Ohkanda, A. Katoh, J. Org. Chem., 60, 1583 (1995); idem, Chem. Lett., 1996, 423
60. K. N. Raymond, S. A. Nguyen, A. Crag, J. Am. Chem. Soc., 115, 6758 (1993)
61. R. Saito, K. K. Ghosh, K. Harada, A. Katoh, Yakugaku Zasshi, 122, 703 (2002)
62. T. Emery, L. Emery, R. K. Olsen, Biochem. Biophys. Chem. Commun., 119, 1191 (1984)
63. B. Lee, M. J. Miller, C. A. Prody, J. B. Neilands, J. Med. Chem., 28, 317 (1985)
64. A. Shanzer, J. Libman, R. Lazar, Y. Tor, Pure & Appl. Chem., 61, 1529 (1989)
65. B. F. Burnham, J. B. Neilands, J. Biol. Chem., 236, 554 (1961)
66. J. B. Neilands, Struct. Bonding, 58, 1 (1984)
67. WHO, Diabetes Mellitus, Reports of a WHO Study Group, WHO Technical Report Series, 1985, p 727 and p 876
68. H. Sakurai, K. Fujii, S. Fujimoto, Y. Fujisawa, K. Takechi, H. Yasui, "ACS Symposium Series 711" ed. by A. S. Tracey, D. C. Crans, American Chemical Society, Washington, DC, 1998, p 344; H. Sakurai, A. Tsuji, "Vanadium in the Environment Part 2" ed. by J. O. Nriagu, John Wiley & Sons, 1998, p 297; H. Sakurai, Y. Fujisawa, S. Fujimoto, H. Yasui, T. Takino, J. Trace Elem. Exp. Med., 12, 393 (1999); H. Sakurai, The Chemical Record, 2, 237 (2002)
69. H. Sakurai, K. Fujii, S. Fujimoto, Y. Fujisawa, K. Takechi, H. Yasui, "ACS Symposium Series 711" ed. by A. S. Tracey, D. C. Crans, American Chemical Society, Washington, DC, 1998, p 344; H. Sakurai, A. Tsuji, "Vanadium in the Environment Part 2" ed. by J. O. Nriagu, John Wiley & Sons, 1998, p 297; H. Sakurai, Y. Fujisawa, S. Fujimoto, H. Yasui, T. Takino, J. Trace Elem. Exp. Med., 12, 393 (1999); H. Sakurai, The Chemical Record, 2, 237 (2002)
70. H. Sakurai, K. Fujii, S. Fujimoto, Y. Fujisawa, K. Takechi, H. Yasui, "ACS Symposium Series 711" ed. by A. S. Tracey, D. C. Crans, American Chemical Society, Washington, DC, 1998, p 344; H. Sakurai, A. Tsuji, "Vanadium in the Environment Part 2" ed. by J. O. Nriagu, John Wiley & Sons, 1998, p 297; H. Sakurai, Y. Fujisawa, S. Fujimoto, H. Yasui, T. Takino, J. Trace Elem. Exp. Med., 12, 393 (1999); H. Sakurai, The Chemical Record, 2, 237 (2002)
71. H. Sakurai, K. Fujii, S. Fujimoto, Y. Fujisawa, K. Takechi, H. Yasui, "ACS Symposium Series 711" ed. by A. S. Tracey, D. C. Crans, American Chemical Society, Washington, DC, 1998, p 344; H. Sakurai, A. Tsuji, "Vanadium in the Environment Part 2" ed. by J. O. Nriagu, John Wiley & Sons, 1998, p 297; H. Sakurai, Y. Fujisawa, S. Fujimoto, H. Yasui, T. Takino, J. Trace Elem. Exp. Med., 12, 393 (1999); H. Sakurai, The Chemical Record, 2, 237 (2002)
72. K. H. Thompson, C. Orvig, J. Chem. Soc., Dalton Trans., 2885 (2000); K. H. Thompson, C. Orvig, Coord. Chem. Rev., 219-221, 1033 (2001)
73. K. H. Thompson, C. Orvig, J. Chem. Soc., Dalton Trans., 2885 (2000); K. H. Thompson, C. Orvig, Coord. Chem. Rev., 219-221, 1033 (2001)
74. Y. Yoshikawa, E. Ueda, K. Kawabe, H. Miyake, H. Sakurai, Y. Kojima, Chem. Lett., 2000, 874; E. Ueda, Y. Yoshikawa, N. Kishimoto, M. Tadokoro, N. Yanagihara, H. Sakurai, Y. Kojima, ibid., 2001, 1184;
75. Y. Yoshikawa, E. Ueda, K. Kawabe, H. Miyake, H. Sakurai, Y. Kojima, Chem. Lett., 2000, 874; E. Ueda, Y. Yoshikawa, N. Kishimoto, M. Tadokoro, N. Yanagihara, H. Sakurai, Y. Kojima, ibid., 2001, 1184;
76. H. Sakurai, K. Fujii, H. Watanabe, H. Tamura, Biochem. Biophys. Res. Commun., 214, 1095 (1995)
77. J. H. McNeil, V. G. Yuen, H. R. Hoveyda, C. Orvig, J. Med. Chem., 35, 1489 (1992)
78. H. Sakurai, H. Sano, T. Takino, H. Yasui, Chem. Lett., 1999, 913
79. M. Melchior, K. H. Thompson, J. M. Jong, S. J. Rettig, E. Shuter, V. G. Yuen, Y. Zhuo, J. H. McNeil, C. Orvig, Inorg. Chem., 38, 2288 (1999)
80. rd International Symposium on Chemistry and Biological Chemistry of Vanadium, 51 (2001)
81. rd International Symposium on Chemistry and Biological Chemistry of Vanadium, 51 (2001)
82. A. Katoh, K. Taguchi, R. Saito, Y. Fujisawa, T. Takino, H. Sakurai, Heterocycles, 60, 1147 (2003)
83. A. Katoh, T. Tsukahara, R. Saito, Y. Yoshikawa, Y. Kojima, H. Sakurai, J. Inorg. Biochem., 86, 293 (2001); A. Katoh, T. Tsukahara, R. Saito, K. K. Ghosh, Y. Yoshikawa, Y. Kojima, A. Tamura, H. Sakurai, Chem. Lett., 2002, 114
84. A. Katoh, T. Tsukahara, R. Saito, Y. Yoshikawa, Y. Kojima, H. Sakurai, J. Inorg. Biochem., 86, 293 (2001); A. Katoh, T. Tsukahara, R. Saito, K. K. Ghosh, Y. Yoshikawa, Y. Kojima, A. Tamura, H. Sakurai, Chem. Lett., 2002, 114
85. M. Nakai, H. Watanabe, C. Fujiwara, H. Kakegawa, T. Satoh, J. Takeda, R. Matsushita, H. Sakurai, Biol. Pharm. Bull., 15, 719 81995)
86. H. Sakurai, H. Sano, T. Takino, H. Yasui, J. Inorg. Biochem., 80, 99 (2000); S. Takeshita, I. Kawamura, T. Yasuno, C. Kimura, T. Yamamoto, J. Seki, A. Tamura, H. Sakurai, T. Goto, ibid., 85, 179 (2001)
87. H. Sakurai, H. Sano, T. Takino, H. Yasui, J. Inorg. Biochem., 80, 99 (2000); S. Takeshita, I. Kawamura, T. Yasuno, C. Kimura, T. Yamamoto, J. Seki, A. Tamura, H. Sakurai, T. Goto, ibid., 85, 179 (2001)