Synthesis of diverse benzo[1,4]oxazin-3-one-based compounds using 1,5-difluoro-2,4-dinitrobenzene

Journal of Combinatorial Chemistry

Volumn 9, Issue 1, 2007, Pages 158-170

  Yuan, Yunyun ^a   Liu, Gang ^a   Li, Li ^a   Wang, Zhanguo ^a   Wang, Lin ^a  

^a INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1 FLUORO 2,4 DINITROBENZENE; 1,5 DIFLUORO 2,4 DINITROBENZENE; 1,5-DIFLUORO-2,4-DINITROBENZENE; BENZOXAZINE DERIVATIVE; DRUG DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

BENZOXAZINES; CHROMATOGRAPHY, LIQUID; COMBINATORIAL CHEMISTRY TECHNIQUES; DINITROFLUOROBENZENE; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE;

EID: 33846615033     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc060094u     Document Type: Article

References (60)

1. Wahidulla, S.; Bhattacharjee, J. J. J. Indian Inst. Sci. 2001, 4, 485-489.
2. Katsura, Y.; Nishino, S.; Takasugi, H. Chem. Pharm. Bull. 1991, 11, 2937-2943.
3. Hassan, G. S. Alexandria J. Pharm. Sci. 2004, 2, 129-137.
4. Kajino, N.; Shibouta, Y.; Nishikawa, K.; Meguro, K. Chem. Pharm. Bull. 1991, 11, 2896-2905.
5. Fringuelli, R.; Pietrella, D.; Schiaffella, F.; Guarraci, A; Perito, S.; Bistoni, F.; Vecchiarelli, A. Bioorg. Med. Chem. 2002, 10, 1681-1686.
6. Dougherty, K. J.; Bannatyne, B. A.; Jankowska, E.; Krutki, P.; Maxwell, D. J. J. Neurosci. 2005, 3, 584-593.
7. Iwahashi, M.; Kobayashi, K.; Nambu, F. Int. Patent Appl. WO 2003078409 A1, 25 September 2003..
8. Vianello, P.; Bandiera, T. U.S. Patent Appl. US 2003073688 A1, 17 April 2003.
9. Anderlub, M.; Cesar, J.; Stefanic, P. Kikelj, D.; Janes, D.; Murn, J.; Nadrah, K.; Tominc, M.; Addicks, E.; Giannis, A.; Stegnar, M.; Dolenc, M. S. Eur. J. Med. Chem. 2005, 1, 25-49.
10. Gellibert, F. J.; Payne, A. Int. Patent Appl. WO 2003097639 A1, 27 November 2003.
11. Nicolaides, D. N.; Gautam, D. R.; Litinas, K. E. Kikelj, D.; Janes, D.; Murn, J.; Nadrah, K.; Tominc, M.; Addicks, E.; Giannis, A.; Stegnar, M.; Dolenc, M. S. J. Heterocycl. Chem. 2004, 4, 605-611.
12. Bethiel, R. S.; Ludeboer, M. U.S. Patent Appl. US 2004097504 A1, 20 May 2004.
13. Caliendo, G.; Perissutti, E.; Santagada, V; Ferdinando, F.; Severino, B.; d'Emmanuele di Villa Bianca, R.; Lippolis, L.; Pinto, A.; Sorrentini, R. Bioorg. Med. Chem. 2002, 10, 2663-2669.
14. (a) Patchett, A. A.; Nargund, R. P. Annu. Rep. Med. Chem. 2000, 35, 289-298.
15. (b) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 7, 1172-1173.
16. (c) Triggle, D. J. Mini-Rev. Med. Chem. 2003, 3, 215-223.
17. (d) DeSimone, R. W.; Currie, K. S.; Mitchell, S. A.; Darrow, J. W.; Pippin, D. A. Comb. Chem. High Throughput Screening 2004, 5, 473-493.
18. (a) Breznik, M.; Mrcina, A.; Kikelj, D. Tetrahedron: Asymmetry 1998, 9, 1115-1116.
19. (b) Breznik, M.; Hrast, V.; Mrcina, A.; Kikelj, D. Tetrahedron: Asymmetry 1999, 10, 153-167.
20. (c) Breznik, M.; Grdaolnik, S. G.; Giester, G.; Leban, I.; Kikelj, D. J. Org. Chem. 2001, 66, 7044-7050.
21. (d) Lee, C. L.; Chan, K. P.; Larn, Y.; Lee, S. Y. Tetrahedron Lett. 2001, 42, 1167-1169.
22. (a) Sicker, D.; Pratorius, B.; Mann, G.; Meyer, L. Synth. Commun. 1989, 211-212.
23. (b) Combs, D. W.; Rampulla, M. S.; Bell, S. C. Klaubert, D. H.; Tobia, A. J.; Falotico, R.; Haertlein, B.; Lakas-Weiss, C.; Moore, J. B. J. Med. Chem. 1990, 33, 380-386.
24. (c) Moussavi, Z.; Depreux, P.; Lesieur, D. Synth. Commun. 1991, 2, 271-278.
25. (d) Atkinson, J.; Morand, P.; Arnason, T. J. Org. Chem. 1991, 56, 1788-1800.
26. (e) Kawakita, T.; Kuroita, T.; Yasumoto, M.; Sano, M.; Inaba, K.; Fukuda, T.; Tahara, T. Chem. Pharm. Bull. 1992, 3, 624-630.
27. (f) Yamamoto, T.; Hori, M.; Watanabe, I.; Tsutsui, H. Harada, K.; Ikeda, S.; Maruo, J.; Morita, T.; Ohtaka, H. Chem. Pharm. Bull. 1997, 12, 1975-1983.
28. (g) Ozden, S.; Ozturk, A. M.; Goker, H.; Altanlar, N. Farmaco 2000, 55, 715-718.
29. Masuoka, Y.; Asako, T.; Goto, G.; Noguchi, S. Chem. Pharm. Bull. 1986, 1, 130-139.
30. (a) Patel, M. V.; Balasubramanium, P.; Balasubramanium, V. Indian J. Chem. 1979, 18B, 245-247.
31. (b) Patel, M. V.; Balasubramanium, P.; Balasubramanium, V. Indian J. Chem. 1979, 18B, 367-368.
32. (c) Shridhar, D. R.; Ram, B.; Rao, K. S.; Jain, M. L. Indian J. Chem. 1985, 24B, 992-994.
33. Caliendo, G.; Perissutti, E.; Santagada, V.; Fiorino, F.; Severino, B.; Cirillo, D.; d'Emmanuele di Villa, B. R.; Lippolis, L.; Pinto, A.; Sorrentini, R. Eur. J. Med. Chem. 2004, 10, 815-826.
34. (a) Zhang, L.; Liu, G.; Zhang, S.-D.; Yang, H.-Zh.; Li, L.; Wu, X.-H.; Yu, J.-L.; Kou, B.-B.; Xu, S.; Li, J.; Sun, G.-Ch.; Ji, Y.-F.; Chen, G.-F. J. Comb. Chem. 2004, 6, 431-436.
35. (b) Wu, X.-H.; Liu, G.; Zhang, J.; Wang, Zh.-G.; Xu, S. Zhang, S.-D.; Zhang, L.; Wang, L. Mol. Diversity 2004, 8, 165-174.
36. (c) Li, L.; Liu, G.; Wang, Zh.-G.; Yuan, Y.-Y.; Zhang, Ch.-X.; Tian, H.-Y. J. Comb. Chem. 2005, 6, 811-821.
37. (a) Krstenansky, J. L.; Cotterill, I. Curr. Opin. Drug Discovery Development 2000, 3, 454-461.
38. (b) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283.
39. (c) Al-Obeidi, Fahad; Austin, R. E.; Okonya, J. F.; Bond, D. R. S. Mini-Rev. Med. Chem. 2003, 3, 449-460.
40. (d) Molteni, V.; Ellis, D. A. Curr. Org. Synth. 2005, 2, 333-375.
41. (a) Wipf, P.; Coleman, C. M.; Janjic, J. M.; Iyer, P. S.; Fodor, M. D.; Shafer, Y. A.; Stephenson, C. R. J.; Kendall, C.; Day, B. W. J. Comb. Chem. 2005, 2, 322-330.
42. (b) Caddick, S.; Wilden, J. D.; Bush, H. D.; Judd, D. B. QSAR Comb. Sci. 2004, 10, 902-905.
43. (a) Ramanjulu, J. M.; Joullie, M. M. Synth. Commun. 1996, 26, 1379-1384.
44. (b) Han, Y.-L.; Chorev, M. J. Org. Chem. 1999, 64, 1972-1978.
45. (c) Sun, S.; Murray, W. V. J. Org. Chem. 1999, 5941-5945.
46. Wang, Zh.-G.; Liu, G.; Yuan, Y.-Y.; Chen, Y.-Y.; Wu, X.-H.; Zhang, S.-M.; Wang, G.-X. J. Comb. Chem. Submitted for publication.
47. Shridhar, D. R.; Ram, B.; Rao, K. S.; Singh, A. N. Indian J. Chem. 1985, 24B, 1293-1294.
48. Ugi, I. Angew. Chem., Int. Ed. Engl. 1962, 1, 8-21.
49. Nakamura, M.; Inoue, J.; Yamada, T. Bioorg. Med. Chem. 2000, 10, 2807-2810.
50. Bethke, T.; Brunkhorst, D.; Van der Leyen, H.; Meyer, W.; Nigbur, R.; Scholz, H. Naunyn-Schmiedeberg's Arch. Pharmacol. 1988, 337, 576-82.
51. Fitzpatrick, L. R.; Decktor, D. L. Agents Actions 1991, 33, 330-336.
52. Landi, C. M. Jpn. Patent JP 2000309545 A2, 7 November 2000.
53. Toja, E. J. Med. Chem. 1984, 27, 610-616.
54. Alaimo, R. J.; Spencer, C. F.; Sheffer, J. B.; Storrin, R. J.; Hatton, C. J.; Kohls, R. E. J. Med. Chem. 1978, 21, 298-300.
55. (a) Liu, G.; Li, L.; Kou, B.-B; Zhang, S.-D.; Zhang, L.; Yuan, Y.-Y.; Ma, T.; Shang, Y.; Li, Y.-Ch. J. Comb. Chem. 2007, submitted for publication.
56. (b) Liu, G. Presented at the Diversity Oriented Synthesis Conference, September 22-23, 2005, Boston, MA.
57. Mukherjee, A.; Akhtar, M. S.; Sharma, V. L.; Seth, M.; Bhaduri, A. P.; Agnihotri, A.; Mehrotra, P. K.; Kamboj, V. P. J. Med. Chem. 1989, 32, 2297-2300.
58. Eckert, B. H.; Forster, B. Angew. Chem., Int. Ed. Engl. 1987, 26, 894-895.
59. Huang, Sh.; Xie, R.-G.; Tian, B.-Zh.; Qing, Sh.-Y. Preparation Handbook of Organic Synthetic Reagents; Science Press: Beijing, China, 2005; pp 330-346. (in Chinese).
60. Liu, G.; Zhang, S.-D.; Zhang, J. China Patent Application CN 03265620.3, 2003.