Efficient microwave-assisted synthesis of new sulfonylbenzimidazole-4,7- diones: Heterocyclic quinones with potential antitumor activity

Tetrahedron

Volumn 60, Issue 41, 2004, Pages 9131-9137

  Boufatah, Narimène ^a   Gellis, Armand ^a   Maldonado, José ^a   Vanelle, Patrice ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Benzimidazole 4,7 diones; Microwave irradiation; S Alkylation; Sulfones

Indexed keywords

1,5,6 TRIMETHYL 2 (2,4,6 TRIMETHYLBENZENESULFONYLMETHYL) 1H BENZIMIDAZOLE 4,7 DIONE; 1,5,6 TRIMETHYL 2 (NAPHTHALENE 1 SULFONYLMETHYL) 1H BENZIMIDAZOLE 4,7 DIONE; 1,5,6 TRIMETHYL 2 (THIOPHENE 2 SULFONYLMETHYL) 1H BENZIMIDAZOLE 4,7 DIONE; 1,5,6 TRIMETHYL 2 (TOLUENE 4 SULFONYLMETHYL) 1H BENZIMIDAZOLE 4,7 DIONE; 2 (4 BROMOBENZENESULFONYLMETHYL) 1,5,6 TRIMETHYL 1H BENZIMIDAZOLE 4,7 DIONE; 2 (4 CHLOROBENZENESULFONYLMETHYL) 1,5,6 TRIMETHYL 1H BENZIMIDAZOLE 4,7 DIONE; 2 (4 FLUOROBENZENESULFONYLMETHYL) 1,5,6 TRIMETHYL 1H BENZIMIDAZOLE 4,7 DIONE; 2 (4 METHOXYBENZENESULFONYLMETHYL) 1,5,6 TRIMETHYL 1H BENZIMIDAZOLE 4,7 DIONE; 2 (BUTANE 1 SULFONYLMETHYL) 1,5,6 TRIMETHYL 1H BENZIMIDAZOLE 4,7 DIONE; 2 BENZENESULFONYLMETHYL 1,5,6 TRIMETHYL 1H BENZIMIDAZOLE 4,7 DIONE; 2 CHLOROMETHYL 1,5,6 TRIMETHYLBENZIMIDAZOLE 4,7 DIONE; BENZIMIDAZOLE DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG SYNTHESIS; METHODOLOGY; MICROWAVE RADIATION; PRIORITY JOURNAL;

EID: 4444361031     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.07.070     Document Type: Article

References (41)

1. B.S. Iyengar, R.T. Dorr, N.G. Shipp, and W.A. Remers J. Med. Chem. 33 1990 253
2. A.C. Sartorelli, W.F. Hodnick, M.F. Belcourt, M. Tomasz, B. Haffty, J.J. Fischer, and S. Rockwell Oncol. Res. 6 1994 501
3. V.S. Li, D. Choi, Z. Wang, L.S. Jimenez, M. Tang, and H. Kohn J. Am. Chem. Soc. 118 1996 2326
4. S. Wang, and H. Kohn J. Med. Chem. 42 1999 788
5. L.Y. Dirix, F. Tonnesen, J. Cassidy, R. Epelbaum, W.W. Ten Bokkel Huinink, N. Pavlidis, R. Sorio, T. Gamucci, I. Wolff, A. Te Velde, J. Lan, and J. Verwei Eur. J. Cancer 32A 1996 2019
6. H.D. Beall, A.R. Hudnott, S. Winsky, D. Siegel, E. Swann, D. Ross, and C.J. Moody Bioorg. Med. Chem. Lett. 8 1998 545
7. H.W. Moore Science 197 1977 527
8. E.B. Skibo, and W.G. Schulz J. Med. Chem. 36 1993 3050
9. E.B. Skibo, I. Islam, M.J. Heileman, and W.G. Schulz J. Med. Chem. 37 1994 78
10. I. Antonini, F. Claudi, G. Cristalli, P. Franchetti, M. Grifantini, and S. Martelli J. Med. Chem. 31 1988 260
11. L. Garuti, M. Roberti, and C. Cermelli Bioorg. Med. Chem. Lett. 9 1999 2525
12. S.-H. Jung, J.-S. Song, H.-S. Lee, S.-U. Choi, and C.-O. Lee Bioorg. Med. Chem. Lett. 6 1996 2553
13. E.-Y. Moon, S.-K. Seong, S.-H. Jung, M. Lee, D.-K. Lee, D.-K. Rhee, S. Pyo, and S.-J. Yoon Cancer Lett. 140 1999 177
14. J.T. Hunt, C.Z. Ding, R. Batorsky, M. Bednarz, R. Bhide, Y. Cho, S. Chong, S. Chao, J. Gullo-Brown, P. Guo, S.H. Kim, F.Y.F. Lee, K. Leftheris, A. Miller, T. Mitt, M. Patel, B.A. Penhallow, C. Ricca, W.C. Rose, R. Schmidt, W.A. Slusarchyk, G. Vite, and V. Manne J. Med. Chem. 43 2000 3587
15. S. Samanta, K. Srikanth, S. Banerjee, B. Debnath, S. Gayen, and T. Jha Bioorg. Med. Chem. 12 2004 1413
16. P. Lidström, J. Tierney, B. Wathey, and J. Westman Tetrahedron 57 2001 9225
17. K. Rad-Moghadam, and M.S. Khajavi J. Chem. Res. (S) 1998 702
18. S. Caddick Tetrahedron 51 1995 10403
19. L. Perreux, and A. Loupy Tetrahedron 57 2001 9199
20. T. Besson, M.-J. Dozias, J. Guillard, P. Jacquault, M.-D. Legoy, and C.W. Rees Tetrahedron 54 1998 6475
21. Gellis, A.; Rathelot, P.; Crozet, M. P.; Vanelle, P. Utility of microwaves as new methodology for electron transfer reactions. In Electron Transfer Reactions in Organic Synthesis; Vanelle, P., Ed.; Research Signpost: Trivandrum, 2002; pp 111-128.
22. B. Perio, M.-J. Dozias, and J. Hamelin Org. Process Res. Dev. 2 1998 428
23. J. Cléophax, M. Liagre, A. Loupy, and A. Petit Org. Process Res. Dev. 4 2000 498
24. B.M. Khalidar, and V.R. Madyar Org. Process Res. Dev. 5 2001 452
25. W.-C. Shieh, S. Dell, and O. Repic Tetrahedron Lett. 43 2002 5607
26. T. Besson, J. Guillard, and C.W. Rees Tetrahedron Lett. 41 2000 1027
27. B. Wathey, J. Tierney, P. Lidström, and J. Westman Drug. Discov. Today 7 2002 373
28. M. Larhed, and A. Hallberg Drug. Discov. Today 6 2001 406
29. P. Vanelle, T. Terme, A. Gellis, and M.P. Crozet Res. Adv. Org. Chem. 1 2000 27
30. Y. Njoya, N. Boufatah, A. Gellis, P. Rathelot, M.P. Crozet, and P. Vanelle Heterocycles 57 2002 1423
31. Y. Njoya, A. Gellis, P. Rathelot, M.P. Crozet, and P. Vanelle Sulfur Lett. 26 2003 67
32. V. Rémusat, T. Terme, A. Gellis, P. Rathelot, and P. Vanelle J. Heterocycl. Chem. 41 2004 221
33. L. Garuti, M. Roberti, M. Malagoli, T. Rossi, and M. Castelli Bioorg. Med. Chem. Lett. 10 2000 2193
34. F. Alvarez, A. Ghérardi, P. Nebois, M.-E. Sarciron, A.-F. Pétavy, and N. Walchshofer Bioorg. Med. Chem. Lett. 12 2002 977
35. L. Garuti, M. Roberti, A. Pession, E. Leoncini, and S. Hrelia Bioorg. Med. Chem. Lett. 11 2001 3147
36. L. Weinberger, and A.R. Day J. Org. Chem. 24 1959 1451
37. L. Smith, and F.L. Austin J. Am. Chem. Soc. 64 1942 528
38. Chai, S.-Y.; Elokdah, H. M.; Sulkowski, T. S. U.S. Patent 6,444,694 B1, 2002; (WO 9639391, 1996; Chem. Abstr. 1997, 126, 117976).
39. W.C. Shieh, S. Dell, and O. RepiČ Org. Lett. 26 2001 4279
40. C. Flader, J. Lui, and R.F. Borch J. Med. Chem. 43 2000 3157
41. L.K. Liu, Y. Chi, and K.-Y. Jen J. Org. Chem. 45 1980 406