Chemistry of quinoline-5,8-diones

Journal of Organic Chemistry

Volumn 63, Issue 2, 1998, Pages 343-346

  Behforouz, Mohammad ^a   Haddad, Jalal ^a   Cai, Wen ^a   Gu, Zhengxiang ^a  

^a BALL STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7 ACETAMIDO 5 ETHYL 5 HYDROXY 2 METHYLQUINOLINE 8 ONE; 7 AMINO 5 ETHYL 5 HYDROXY 2 METHYLQUINOLINE 8 ONE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CATALYSIS; CELL TRANSFORMATION; DERIVATIZATION; DRUG SYNTHESIS; NONHUMAN; STRUCTURE ANALYSIS;

EID: 0032559261     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971823i     Document Type: Article

References (50)

1. (a) Behforouz, M.; Merriman, R. L. U.S. Patent No. 5,646,150, 1997.
2. (b) Behforouz, M.; Merriman, R. L. U.S. Patent No. 5,525,611, 1996.
3. (c) Behforouz, M.; Merriman, R. L. PCT Int. Appl. WO 94 29308, 1994; Chem. Abstr. 122, 239454a.
4. (d) Ryu, C. K.; Kim, H. J. Arch. Pharm. Res. 1994, 17, 139.
5. (e) Jain, R.; Gupta, R. C.; Anand, N. Indian J. Chem. 1994 33B, 792.
6. (f) Inouye, Y.; Matsumoto, H.; Morishige, R.; Kiathara, Y.; Kubo, A.; Nakamura, S. Chem. Pharm. Bull. 1991, 39, 994.
7. (g) Take, Y.; Oogose, K.; Kubo, T.; Inouye, Y.; Nakamura, S.; Kiathara, Y.; Kubo, A. J. Antibiot. 1987, 40, 679.
8. (h) Boger, D. L.; Yasuda, M.; Mitscher, L. A.; Drake, S. D.; Kitos, P. A.; Thompson, S. C. J. Med. Chem. 1987, 30, 1918.
9. (i) Bachur, N. R.; Gordon, S. L.; Gee, M. Y. Cancer Res. 1978, 38, 1745.
10. (j) Hibino, S. Heterocycles 1977, 6, 1485.
11. (k) Wan, Y. P.; Porte, T. H.; Folkers, K. J. Heterocycl. Chem. 1974, 11, 519.
12. (l) Lown, J. W.; Sim, S-K. Can. J. Chem. 1976, 54, 2563.
13. (m) Babu, B. H.; Rao, N. V. S. Heterocycles 1977, 6, 1485.
14. (a) Rao, K. V.; Cullen, W. P. Antibiot. Annu. 1959-1960, 950.
15. (b) Rao, K. V.; Biemann, K.; Woodward, R. B. J. Am. Chem. Soc. 1963, 85, 2532.
16. Herlt, A. J.; Rickards, R. W.; Wu, J.-P. J. Antibiot. 1985, 38, 516.
17. (a) Doyle, T. W.; Balitz, D. M.; Grulich, R. E.; Nettleton, D. E.; Gould, S. J.; Tann, C.; Moews, A. E. Tetrahedron Lett. 1981, 22, 4595.
18. (b) Balitz, D. M.; Bush, J. A.; Bradner, W. T.; Doyle, T. W.; O'Herron, F. A.; Nettleton, D. E. J. Antibiot. 1982, 35, 259.
19. Rao, K. V. Cancer Chemother. Rep., Part 2 1974, 4(2), 1.
20. (a) Behforouz, M.; Gu, Z.; Stelzer, L. S.; Ahmadian, M.; Haddad, J.; Scherschel, J. A. Tetrahedron Lett. 1997, 38, 2211.
21. (b) Behforouz, M.; Haddad, J.; Cai, W.; Arnold, M. B.; Mohammadi, F.; Sousa, A. C.; Horn, M. A. J. Org. Chem. 1996, 61, 6552.
22. (c) Kiathara, Y.; Yonezawa, T.; Kubo, A. Heterocycles, 1994, 38, 1919.
23. (d) Behforouz, M.; Gu, Z.; Cai, W.; Horn, M. A.; Ahmadian, M. J. Org. Chem. 1993, 58, 7089.
24. (e) Kiathara, Y.; Nakahara, S.; Shimizu, M.; Yonezawa, T.; Kubo, A. Heterocycles 1993, 36, 1909.
25. (f) Yanni, A. S. Collect. Czech. Chem. Commun. 1991, 56, 1919.
26. (g) Kaiya, T.; Kawazoe, Y.; Ono, M.; Tamura, S. Heterocycles 1988, 27, 645.
27. (h) Boger, D. L.; Duff, S. R.; Panek, J. S.; Yasuda, M. J. Org. Chem. 1985, 50, 5782.
28. (i) Liao, T. K.; Nyberg, W. H.; Cheng, C. C. J. Heterocycl. Chem. 1976, 13, 1063.
29. (j) Hibino, S.; Weinreb, S. M. J. Org. Chem. 1977, 42, 232.
30. (k) Kende, A. S.; Ebetino, F. H. Tetrahedron Lett. 1984, 25, 923.
31. (l) Boger, D. L.; Duff, S. R.; Panek, J. S.; Yasuda, M. J. Org. Chem. 1985, 50, 5790.
32. (m) Hibino, S.; Okazaki, M.; Ichikawa, M.; Sato, K.; Ishizu, T. Heterocycles 1985, 23, 261.
33. (n) Rao, A. V. R.; Chavan, S. P.; Sivadasan, L. Tetrahedron 1986, 42, 5065.
34. (o) Rao, K. V. J. Heterocyclic Chem. 1977, 14, 653 and references therein.
35. (a) Kametani, T.; Ogasawara, K. J. Pharm. Soc. Jpn. 1966, 86, 55.
36. (b) Rao, K. V. J. Hetrocyclic Chem. 1975, 12, 725.
37. (c) Pratt, Y. T.; Drake, N. L. J. Am. Chem. Soc. 1960, 82, 1155.
38. (d) Pratt, Y. T.; Drake, N. L. J. Org. Chem. 1962, 27, 3905.
39. (e) Wan, Y. P.; Porter, T. H.; Folkers, K. Proc. Nat. Acad. Sci. U.S.A. 1974, 71(3), 952-6.
40. (f) Yoshida, K.; Ishiguro, M.; Honda, H.; Yamamoto, M.; Kubo, Y. Bull. Chem. Soc. Jpn. 1988, 61, 1(12), 4335 (Eng).
41. Haber, A. Org. Prep. Proced. Int. 1987, 19 (2-3), 249-50.
42. (a) For a review see: Nagata, W.; Yoshioka, M. Org. React. 1977, 255.
43. (b) Asaoka, M.; Sonoda, S.; Naoaki, F.; Takei, A. Tetrahedron 1990, 46, 1541.
44. (c) Dahuron, N.; Langlois, N.; Chiaroni, A.; Riche, C. Heterocycles 1996, 42, 635.
45. Kubo, A.; Kitahara, Y.; Inaba, K. Heterocycles 1985, 23, 387 and references therein.
46. We plan to expand this reaction to other quinolinediones and quinones.
47. (a) Garcia Ruano, J. L.; Martin Castro, A. M.; Rodriguez, J. H. J. Org. Chem. 1992, 57, 7235.
48. (b) Escribano, A.; Garcia Ruano, J. L.; Martin Castro, A. M.; Rodriguez, J. H. Tetrahedron 1994, 50, 7567.
49. (a) Brown, H. C.; Zweifel, G. J. J. Am. Chem. Soc. 1960, 82, 4708.
50. (b) Wang, K. K.; Brown, H. C. J. Org. Chem. 1980, 45, 5303.