1,4-Dihydro-2,3-quinoxalinediones as potential flavin metabolites and excitatory amino acid receptor ligands. Part 1: Synthesis and pharmacological evaluation of the benzylic oxidation series of 1,4-dihydro-6,7-dimethyl-2,3- quinoxalinedione

Bioorganic and Medicinal Chemistry

Volumn 6, Issue 3, 1998, Pages 271-282

  Bhat, Ajita ^a   Chang, Hui Min ^a   Wallace, Lane J ^b   Weinstein, David M ^b   Shams, Gamal ^b   Garris, Cynthia C ^a   Hill, Ronald A ^a  

^a UNIVERSITY OF LOUISIANA AT MONROE   (United States)

^b OHIO STATE UNIVERSITY   (United States)

Author keywords

Glutamate; Metabolite; Quinoxalinedione; Riboflavin

Indexed keywords

1,4 DIHYDRO 2,3 QUINOXALINEDIONE; ALPHA AMINO 3 HYDROXY 5 METHYL 4 ISOXAZOLEPROPIONIC ACID; AMPA RECEPTOR ANTAGONIST; EXCITATORY AMINO ACID RECEPTOR; QUERCETIN; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID BRAIN LEVEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; DRUG OXIDATION; DRUG SYNTHESIS; NONHUMAN; RAT;

ANIMALS; BINDING, COMPETITIVE; BRAIN; EXCITATORY AMINO ACID ANTAGONISTS; FLAVINS; LIGANDS; MICE; QUINOXALINES; RATS; RECEPTORS, GLUTAMATE; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA;

EID: 0031941263     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(97)10032-3     Document Type: Article

References (70)

1. (a) Blake, J. F.; Yates, R. G.; Brown, M. W.; Collingridge, G. L. Br J Pharmacol. 1989, 97, 71.
2. (b) Honoré, T.; Davies, S. N.; Drejer, J.; Fletcher, E.; Jacobsen, P.; Lodge, D.; Nielsen, F. E. Science 1988, 241, 701.
3. (c) Watkins, J. C.; Krogsgaard-Larsen, P.; Honoré, T. Trends Pharmacol. Sci. 1990, 11, 25.
4. (a) Verdoorn, T. A.; Kleckner, N. W.; Dingledine, R. Mol Pharmacol. 1989, 35, 360.
5. (b) Goldstein, J. M.; Litwin, L. C. Mol. Chem. Neuropathol. 1993, 18, 145.
6. (c) Randle, J. R. C.; Guet, T.; Bobichon, C.; Moreau, C.; Curutchet, P.; Lambolezz, B.; Carvalho, L. P. D.; Cordi, A.; Lepagnol, J. M. Molec Pharmacol. 1992, 41, 337.
7. (d) Lester, R. A.; Quarum, M. L.; Parker, J. D.; Weber, E.; Jahr, C. E. Mol. Pharmacol. 1989, 35, 565.
8. See, for example (and references therein): (a) Desos, P.; Lepagnol, J. M.; Morain, P.; Lestage, P.; Cordi, A. A. J. Med. Chem. 1996, 39, 197.
9. (b) Guzikowski, A. P.; Cai, S. X.; Espita, S. A.; Hawkinson, J. E.; Huettner, J. E.; Nogales, D. F.; Tran, M.; Woodward, R. M.; Weber, E.; Keana, J. F. W. J. Med. Chem. 1996, 39, 4643.
10. (c) Ohmori, J.; Shimizu-Sasamata, M.; Okada, M.; Sakamoto, S. J. Med. Chem. 1996, 39, 3971.
11. (d) Hays, S. J; Boxer, P. A.; Taylor, C. P.; Vartarian, M. G.; Robichaud, L. J.; Nielsen, E. Ø. Bioorg. Med. Chem. Lett. 1993, 3, 77.
12. (e) Wätjen, F.; Nielsen, E, Ø.; Drejer, J.; Jensen, L. H. Bioorg. Med. Chem. Lett. 1993, 3, 105.
13. (f) Carling, R. W.; Leeson, P. D.; Moore, K. W.; Smith, J. D.; Moyes, C. R.; Mawer, I. M.; Thomas, S.; Chan, T.; Baker, R.; Foster, A. C.; Grimwood, S.; Kemp, J. A.; Marshall, G. R.; Tricklebank, M. D.; Saywell, K. L. J. Med. Chem. 1993, 36, 3397.
14. (a) Buchan, A. M.; Lesiuk, H.; Barnes, K.A.; Li, H.; Huang, Z. G.; Smith, K. E.; Xue, D. Stroke 1993, 24 [suppl I] I148.
15. (b) Gill, R. Cerebrovasc. Brain. Metab. Rev. 1994, 6, 225.
16. (c) Shimizu-Sasamata, M.; Kawasaki-Yatsugi, S.; Okada, M.; Sakamoto, S.; Yatsugi, S.; Togami, J.; Hatanaka, K.; Ohmori, J.; Koshiya, K.; Usuda, S.; Murase, K. J. Pharmacol. Exp. Ther. 1996, 276, 84.
17. (d) Graham, S. H.; Chen, J.; Lan, J. Q.; Simon, R. P. J. Pharmacol. Exp. Ther. 1996, 276, 1.
18. (e) Ginsberg, M. D. Neuroscientist 1995, 1, 95.
19. (f) Sheardown, M. J.; Suzdak, P. D.; Nordholm, L. Eur. J. Pharmacol. 1993, 236, 347.
20. Tsai, L.; Stadtman, E. R. Methods Enzymol. 1971, 18, 557.
21. Tsai, L.; Smyrniotis P. Z.; Harkness, D.; Stadtman, E. R. Biochem. Z 1963, 338, 561.
22. Harkness, D. R.; Tsai, L.; Stadtman, E. R. Arch. Biochem. Biophys. 1964, 108, 323.
23. Harkness, D. R.; Stadtman, E. R. J. Biol. Chem. 1965, 240, 4089.
24. Kato, Y.; Makida, H. Gifu Yakka Daigaku Kiyo 1964, 14, 38. (Also referenced in Chem. Abstr. 1966, 64, 16309g.).
25. Kato, Y.; Makida, H. Gifu Yakka Daigaku Kiyo 1964, 14, 38. (Also referenced in Chem. Abstr. 1966, 64, 16309g.).
26. Surrey, A. R.; Nachod, F. C. J. Am. Chem. Soc. 1951, 73, 2336.
27. Hotta, K.; Terao, M. Bitamin. 1959, 17, 539. (Also referenced in Chem. Abstr. 1963, 59, 9018c).
28. Hotta, K.; Terao, M. Bitamin. 1959, 17, 539. (Also referenced in Chem. Abstr. 1963, 59, 9018c).
29. (a) Ina, S. Tohoku Igaku Zassi 1959, 59, 13.
30. (b) Idem. Ibid 1959, 59, 19.
31. Miles, H. T.; Smyrniotis, P. Z.; Stadtman, E. R. J. Am. Chem. Soc. 1959, 81, 1946.
32. Saito, I.; Matsuura, T. Biochemistry 1967, 6, 3602.
33. (a) Cai, S. X.; Weber, E.; Keana, J. F. W.; Kher, S. PCT Int Appl WO 95 12,417 (Cl. A61K51/00), 11 May 1995, US Appl 148 259, 5 Nov 1993, 94,.
34. (b) Oguchi, S.; Yamamoto, M.; Aida, T.; Yoshino, R. Tokyo Gakugei Daigaku Kiyo, Dai-4-bumon 1981, 33, 115.
35. (c ) Ahmad, Y.; Habib, M. S.; Iqbal, M.; Qureshi M. I. Ziauddin. Can. J. Chem. 1965, 43, 3424.
36. (d) Kazimierczuk, Z.; Pfleiderer, W. Liebigs. Ann. Chem. 1982, 754.
37. (e) Cheeseman, G. H. W. J. Chem. Soc. 1961, 1246.
38. Hill, Ronald A. Ph D Dissertation, The Ohio State University, 1991. Hill, R. A.; Wallace, L. J.; Miller, D. D.; Bhat, A. R.; Supko, D.; Shams, G.; Tai, H.; Layer R. T.; Weinstein, D.; Willins, D.; Uretsky, N. J. Document in preparation.
39. Cf.: Sastry, C. V. R.; Jogibhukta, M.; Krishnan, V. S. H.; Rao, K. S.; Vemana, K.; Shridhar, D. R.; Tripathi, R. M.; Verman, R. K.; Kaushal, R. Indian J. Chem. Sect. B 1988, 27B, 1110.
40. Leeson, P. D.; Baker, R.; Carling, R. W.; Curtis, N. R.; Moore, K. W.; Williams, B. J.; Foster, A. C.; Donald, A. E.; Kemp, J. A.; Marshall, G. R. J. Med. Chem. 1991, 34, 1243.
41. Cf.: Ohkawa, H.; Ohishi, N.; Yagi, K. J. Biol. Chem. 1983, 258, 5623.
42. Furniss, B. S.; Hannafford, A. J. editors. Vogel's Textbook of Practical Organic Chemistry, 5th ed. Harlow:English Language Book Society/Longman, UK, 1989, 1003-1004.
43. Goldstein, H.; Tardent, A. Helv. Chim. Acta. 1951, 34, 149.
44. Tillotson, J. A.; Karcz, M. S. J. Nutr. 1977, 107, 1269.
45. Christensen, S. Acta. Pharmacol. Toxicol. 1971, 29, 428. See also Idem Ibid 1971, 30, 141; Idem Ibid 1971, 30, 177; Idem Ibid 1973, 32, Suppl.), 3.
46. Christensen, S. Acta. Pharmacol. Toxicol. 1971, 29, 428. See also Idem Ibid 1971, 30, 141; Idem Ibid 1971, 30, 177; Idem Ibid 1973, 32, Suppl.), 3.
47. Christensen, S. Acta. Pharmacol. Toxicol. 1971, 29, 428. See also Idem Ibid 1971, 30, 141; Idem Ibid 1971, 30, 177; Idem Ibid 1973, 32, Suppl.), 3.
48. Christensen, S. Acta. Pharmacol. Toxicol. 1971, 29, 428. See also Idem Ibid 1971, 30, 141; Idem Ibid 1971, 30, 177; Idem Ibid 1973, 32, Suppl.), 3.
49. Hotta, K.; Munetaka, M.; Hayashi, F.; Kato, S.; Sugito, R. Bitamin 1958, 14, 57. (Also referenced in Chem. Abstr. 1960, 54, 22918a).
50. Hotta, K.; Munetaka, M.; Hayashi, F.; Kato, S.; Sugito, R. Bitamin 1958, 14, 57. (Also referenced in Chem. Abstr. 1960, 54, 22918a).
51. Owen, E. C.; West, D. W.; Coates, M. Br. J. Nutr. 1970, 24, 259.
52. Owen, E. C.; West, D. W. Br. J. Nutr. 1970, 24, 45.
53. Hotta, K.; Ando, O. J Vitaminol. (Kyoto) 1961, 7, 196.
54. Hotta, K.; Ando, O. Bitamin. (Kyoto) 1961, 23, 247. (Also referenced in Chem. Abstr. 1964, 61, 16416a.).
55. Hotta, K.; Ando, O. Bitamin. (Kyoto) 1961, 23, 247. (Also referenced in Chem. Abstr. 1964, 61, 16416a.).
56. Hotta, K.; Ishiguro, I.; Tanaka, K.; Ando, O.; Imaizumi, S. Nagoya J. Med. Sci. 1958, 21, 46.
57. Ogunmodede, B. K.; McCormick, D. B. Proc. Soc. Exp. Biol. Med. 1966, 122, 845.
58. Papavassiliou, G. C.; Yiannopoulos, S. Y.; Zambounis, J. S. Chem. Scr. 1987, 27, 265.
59. Eicken, K.; Spiegler, W.; Wuerzer, B.; Meyer, N. Ger Offen DE 3,533,791 (Cl. C07D241/44), 26 March 1987, 7.
60. Mayer, M. J. Prakt. Chem. (2) 1915, 92, 137.
61. Jacobsen, O. Ber. Dtsch. Chem. Ges. 1884, 17, 162.
62. Peltier, D. Bull. Soc. Sci. Bretagne. 1956, 31, 7. See also Peltier, D. Compt. Rend. 1952, 235, 1660.
63. Peltier, D. Bull. Soc. Sci. Bretagne. 1956, 31, 7. See also Peltier, D. Compt. Rend. 1952, 235, 1660.
64. Hannig, E.; Wilhelm, H. Pharmazie 1969, 24, 29.
65. Cf.: Sastry, C. V. R.; Rao, K. S.; Krishana, V. S. H.; Rastogi, K.; Jain, M. L. Indian J. Chem. Sect. B 1989, 28B, 888.
66. Honoré, T.; Laridsen, J.; Krogsgaard-Larsen, P. J. Neurochem. 1982, 38, 173.
67. Honoré, T.; Drejer, J.; Nielsen, E. Ø.; Nielsen, M. Biochem. Pharmacol. 1989, 38, 3207.
68. Pittaluga, A.; Raiteri, M. J. Pharmacol. Exp. Ther. 1992, 260, 232.
69. Desai, M. A.; Burnette, J. P.; Schoepp, D. D. J. Neurochem. 1994, 63, 231.
70. Chou, T. C.; Talalay, P. Trends Pharmacol. Sci. 1983, 4, 450.