Synthesis of some ethyl 3-(aryldiazenyl)-7-oxo-dihydropyrido[2,3-f] quinoxaline-8-carboxylates

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 62, Issue 8, 2007, Pages 1045-1051

  Zahra, Jalal A ^a   Khanfar, Monther A ^a   El Abadelah, Mustafa M ^a   Thaher, Bassam A Abu ^b   El Abadla, Naser S ^c   Voelter, Wolfgang ^d  

^a UNIVERSITY OF JORDAN   (Jordan)

^b ISLAMIC UNIVERSITY OF GAZA   (Palestine)

^c AL AQSA UNIVERSITY   (Palestine)

^d UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

7,8 diamino 4 oxoquinoline 3 carboxylate; Ethyl 7 oxopyrido 2,3 f quinoxaline 8 carboxylates; acetyl N arylhydrazonoyl chlorides

Indexed keywords

ADDITION REACTIONS; CHLORINE COMPOUNDS;

7,8-DIAMINO-4-OXOQUINOLINE-3-CARBOXYLATE; CHEMICAL REDUCTION; CYCLOCONDENSATION REACTIONS; FREE ACIDS; NUCLEOPHILIC ADDITIONS; QUINOXALINES; SITE SELECTIVE; TRIETHYLAMINES;

CARBOXYLATION;

EID: 35348989747     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-2007-0807     Document Type: Article

References (56)

1. a) M. J. Waring, K. R. Fox, Topics in Molecular and Structural Biology 1983, 3, 127-156;
2. b) M. J. Waring, NATO ASI Series, Series A: Life Sciences 1987, 137, 113-126;
3. c) S. Neidle, J. M. Waring, Molecular Aspects of Anticancer Drug-DNA Interactions, Macmillan, Basingstoke, UK, 1993, 213-242.
4. a) S. Gerchakov, P. J. Whitman, H. P. Schultz, J. Med. Chem. 1966, 9, 266-268;
5. b) H. Otsuka, T. Shoji, Tetrahedron 1967, 23, 1535-1542;
6. c) T. Yoshida, K. Katagiri, Biochemistry 1969, 8, 2645-2651;
7. d) S. Gerchakov, H. P. Schultz, J. Med. Chem. 1969, 12, 141-144;
8. e) R. K. Olsen, J. Heterocycl. Chem. 1970, 7, 435-437.
9. a) A. E. A. Porter, in Comprehensive Heterocyclic Chemistry: Pyrazines and Their Benzo Derivatives, Vol. 3, Part 2B (Eds.: A. R. Katritzky, C. W. Rees, A. J. Boulton, S. McKillop), Pergamon Press, Oxford, 1984, pp. 157-197;
10. b) G. W. H. Cheeseman, A. F. Cookson, Chem. Heterocycl. Compds., Vol. 35 (Eds.: A. Wiessberger, E. C. Taylor), John Wiley, New York, 1979, pp. 1-290.
11. J. Ohmori, S. Sakamoto, H. Kubota, M. Shimizu-Sasamata, M. Okada, S. Kawasaki, K. Hidaka, J. Togami, T. Furuya, K. Murase, J. Med. Chem. 1994, 37, 467-475.
12. a) G. Sakata, K. Makino, Y. Kurasawa, Heterocycles 1988, 27, 2481-2515;
13. b) S. Gobec, U. Urleb, Science of Synthesis 2004, 16, 845-911;
14. c) D. J. Brown, Chemistry of Heterocyclic Compounds: Quinoxalines, Supplement 2, Vol. 61, Parts i-xvi, John Wiley, New York, 2004, pp. 1-510.
15. K. Makino, G. Sakata, K. Morimoto, Y. Ochiai, Heterocycles 1985, 23, 2025-2034.
16. a) A. Boido, I. Vazzana, F. Sparatore, Farmaco 1994, 49, 97-104;
17. b) A. Monge, J. A. Palop, A. L. de Cerain, V. Senaedor, F. J. Martinez-Crespo, Y. Sainz, S. Narro, E. Garcia, C. de Miguel, M. Gonzalez, E. Hamilton, A. J. Barker, E. D. Clarke, D. T. Geenhow, J. Med. Chem. 1995, 38, 1786-1792.
18. A. Nayyar, R. Jain, Current Med. Chem. 2005, 12, 1873-1886.
19. D. Catarzi, L. Cecchi, V. Colotta, G. Filacchioni, C. Martini, P. Tacchi, A. Lucacchini, J. Med. Chem. 1995, 38, 1330-1336.
20. D. Catarzi, L. Cecchi, V. Colotta, F. Melani, G. Filacchioni, C. Martini, L. Giusti, A. Lucacchini, J. Med. Chem. 1994, 37, 2846-2850.
21. a) H. Koga, A. Itoh, S. Murayama, T. Irikura, J. Med. Chem. 1980, 23, 1358-1363;
22. b) V. T. Andriole, The Quinolones, Academic Press, London, 1988;
23. c) T. D. Gootz, K. E. Brighty, Med. Res. Rev. 1996, 16, 433-486;
24. d) Y. Kuramoto, Y. Ohshita, J. Yoshida, A. Yazaki, M. Shiro, T. Koike, J. Med. Chem. 2003, 46, 1905-1917;
25. e) X. E. Hu, N. K. Kim, J. L. Gray, J.-I. K. Almstead, W. L. Seibel, B. Ledoussal, J. Med. Chem. 2003, 46, 3655-3661.
26. For reviews see: a) D. T. W. Chu, P. B. Fernandes, Adv. Drug Res. 1991, 21, 39-144;
27. b) L. M. Domagala, J. Antimicrob. Chemother. 1994, 33, 685-706;
28. c) A. D. Da Silva, M. V. De Almeida, M. V. N. De Souza, M. R. C. Couri, Current Med. Chem. 2003, 10, 21-39;
29. d) L. A. Mistcher, Chem. Rev. 2005, 105, 559-592.
30. R. Wise, J. M. Andrews, L. J. Edwards, Antimicrob. Agents Chemother. 1983, 23, 559-564.
31. T. Yoshinari, E. Mano, H. Arakawa, M. Kurama, T. Iguchi, S. Nakagawa, N. Tanaka, A. Okura, Jpn. J. Cancer Res. 1993, 84, 800-806.
32. a) H. Arakawa, E. Mano, N. Hakoda, T. Yoshinari, S. Nakagawa, A. Okura, Anti-cancer Drug Res. 1996, 11, 221 -229;
33. b) C. Nishijima, K. Kawada, K. Ohara, T. Shinomiya, S. Fukuda, A. Nakamura, T. Sawai, M. Ikekita, Res. Comm. Biochem. Cell Mol. Biol. 2002, 6, 21-38;
34. c) K. D. Bromberg, A. B. Burgin, N. Osheroff, Biochemistry 2003, 42, 3393-3398.
35. a) J. Saloň, V. Milata, N. Prónayová, J. Leško, Monatsh. Chem. 2000, 131, 293-299;
36. b) J. Saloň, V. Milata, M. Chudik, N. Prónayová, J. Leško, M. Seman, A. Belicová, Monatsh. Chem. 2004, 135, 283-291.
37. a) K. Grohe, H. Heitzer, Liebigs Ann. Chem. 1987, 29-37;
38. b) U. Petersen, K. Grohe, T. Schenke, H. Hagemann, H. J. Zeiler, K. G. Metzger, Ger. Offen. 3601567, 1987;
39. c) R. M. Pulla, C. N. Venkaiah, P. CT Int. Appl. WO 085692, 2001.
40. J. P. Sanchez, J. M. Domagala, S. E. Hagen, C. L. Heifetz, M. P. Hutt, J. B. Nichols, A. K. Trehan, J. Med. Chem. 1988, 31, 983-991.
41. M. Al-Hiari, M. A. Khanfar, A. M. Qaisi, M. Y. Abu Shuheil, M. M. El-Abadelah, R. Boese, Heterocycles 2006, 68, 1163-1172.
42. P. Frohberg, M. Wiese, P. Nuhn, Arch. Pharm. Med. Chem. 1997, 330, 47-52.
43. a) A. S. Shawali, C. J. Párkányi, J. Heterocycl. Chem. 1980, 17, 833-854;
44. b) A. S. Shawali, Heterocycles 1983, 20, 2239-2285;
45. c) A. S. Shawali, Chem. Rev. 1993, 93, 2731-2777.
46. a) M. O. Lozinskii, P. S. Pelkis, Zh. Org. Khim. 1965, 1, 1793-1799;
47. b) M. O. Lozinskii, P. S. Pelkis, Zh. Org. Khim. 1966, 2, 692-697;
48. c) N. E. Mackenzie, R. H. Thomas, C. W. Greenhalgh, J. Chem. Soc., Perkin Trans. 1, 1980, 2923-2932;
49. d) N. Almirante, L. Foti, J. Heterocycl. Chem. 1983, 20, 1523-1524;
50. e) C. J. Párkányi, O. A. Abdelhamid, A. S. Shawali, J. Heterocycl. Chem. 1984, 21, 521-524.
51. a) M. M. El-Abadelah, A. Q. Hussein, B. A. Abu Thaher, Heterocycles 1991, 32, 1879-1895;
52. b) N. F. Eweiss, A. Osman, J. Heterocycl. Chem. 1980, 17, 1713-1717.
53. R. Fusco, R. Romani, Gazz. Chem. Ital. 1946, 76, 419-438.
54. a) R. R. Phillips, Org. React. 1959, 10, 143-178;
55. b) H. C. Yao, P. Resnick, J. Am. Chem. Soc. 1962, 84, 3514-3517;
56. c) G. C. Barrett, M. M. El-Abadelah, M. K. Hargreaves, J. Chem. Soc. (C), 1970, 1986-1989.