Combinatorial synthesis of biheterocyclic benzimidazoles by microwave irradiation

Combinatorial Chemistry and High Throughput Screening

Volumn 7, Issue 3, 2004, Pages 251-255

  Yeh, Wen Bing ^a   Lin, Mei Jung ^a   Sun, Chung Ming ^a  

^a NATIONAL DONG HWA UNIVERSITY   (Taiwan)

Author keywords

Biheterocyclic benzimidazole; Combinatorial synthesis; Microwave irradiation

Indexed keywords

1,2 PHENYLENEDIAMINE; 3 NITROBENZOIC ACID; 4 FLUORO 3 NITROBENZOIC ACID; 5 (BENZIMIDAZOL 2 YL)BENZIMIDAZOLE DERIVATIVE; AMIDE; AMINE; AROMATIC AMINO ACID; BENZIMIDAZOLE DERIVATIVE; HETEROCYCLIC COMPOUND; ISOTHIOCYANIC ACID DERIVATIVE; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; COMBINATORIAL CHEMISTRY; CYCLIZATION; MICROWAVE IRRADIATION; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 2942525076     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: 10.2174/1386207043328878     Document Type: Article

References (35)

1. (a) Lenz, G. R.; Nash, H. M.; Jindal, S. Drug Discovery Today 2000, 5, 145-156.
2. (b) Falb, D.; Jindal, S. Curr. Opin. Drug Dis. Dev. 2002, 5, 1367-6733.
3. (a) Dolle, R. E. Mol. Diversity., 1996, 2, 223-236.
4. (b) Dolle R. E.; Nelson, K. H. J. Comb. Chem. 1999, 1, 235-282.
5. (c) Dolle, R. E. J. Comb. Chem. 2000, 2, 383-433.
6. (d) Dolle, R. E. J. Comb. Chem. 2001, 3, 477-517.
7. (e) Dolle, R. E. J. Comb. Chem. 2003, 5, 693-753.
8. Book chapter: Sun, C. M. In Combinatorial Chemistry Methods and Protocols, Methods in Molecular Biology Series; Bellavance, L; Ed.; The Humana Press Inc.: New Jersey, 2002; Chapter 10, pp 345-371.
9. Franzén, R. J. Comb. Chem. 2000, 2, 195-214.
10. Shey, J. Y.; Sun, C. M. Tetrahedron Lett. 2002, 43, 1725-1729.
11. Microwave-assisted solid-phase combinatorial synthesis: (a) Stadler, A.; Kappe, C. O. J. Comb. Chem. 2001, 3, 624-630.
12. (b) Wilson, N. S.; Roth, G. P. Curr. Opin. Drug Dis. Dev. 2002, 5, 620-629.
13. (c) Al-Obeidi, F.; Austin, R. E.; Okonya, J. F.; Bond, D. R. S. Mini. Rev. Med. Chem. 2003, 3, 459-470.
14. (d) Swamy, K. M. K.; Lin, M. J.; Yeh, W. B. and Sun, C. M. Curr. Med. Chem. 2003, 10, 2403-2424.
15. (a) Kohara, Y.; Kubo, K.; Imamiya, I.; Wada, T.; Inada, Y.; Naka, T. J. Med. Chem. 1996, 39, 5228-5235.
16. (b) Roth, T.; Morningstar, M. L.; Boyer, P. L.; Hughes, S. H.; Buckheit, R. W.; Micheda, C. J. J. Med. Chem. 1997, 40, 4199-4207.
17. (c) Porcari, A. R.; Devivar, R. V.; Kucera, L. S.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 1998, 41, 1252-1262.
18. (d) Zarrinmayeh, H.; Nunes, A. M.; Ornstein, P. L.; Zimmernan, D. M.; Arnold, M. B.; Schober, D. A.; Gackenheimer, S. L.; Bruns, R. F.; Hipskind, P. A.; Britton, T. C.; Cantrell, B. E.; Gehlert, D. R. J. Med. Chem. 1998, 41, 2709-2719.
19. (e) Gua, Z.; Zhou, D.; Schultz, P. G. Science 2000, 288, 2042-2045.
20. Reddy, B. S. P.; Sharma, S. K.; Lown, J. W. Curr. Med. Chem. 2001, 8, 475-508.
21. Ries, U. J.; Mihm, G.; Narr, B.; Hasselbach, K. M.; Wittneben, H.; Entzeroth, M.; van Meel, J. C. A.; Wiener, W.; Hauel, N. H. J. Med. Chem. 1993, 36, 4040-4051.
22. (a) Mann, J.; Baron, A.; Boahen, Y. O.; Johansson, E.; Parkinson, G.; Kelland, L. R.; Neidle, S. J. Med. Chem. 2001, 44, 138-144.
23. (b) Rastogi, K.; Chang, J. Y.; Pan, W. Y.; Chen, C. H.; Chou, T. C.; Chen, L. T.; Su, T. L. J. Med. Chem. 2002, 45, 4485-4493.
24. (c) Tawar, U.; Jain, A. K.; Dwarakanath, B. S.; Chandra, R.; Singh, Y.; Chaudhuru, N. K.; Khaitan, D.; Tandon, V. J. Med. Chem. 2003, 46, 3785-3792.
25. (a) Jin, S.; Kim, J. S.; Sim, S. P.; Lin, A.; Pilch, D. S.; Liu, L. F.; LaVoie, E. J. Bioorg. Med. Chem. Lett. 2000, 10, 719-723.
26. (b) Satz, A. L.; Bruice, T. C. Acc. Chem. Res. 2002, 35, 86-95.
27. Kelly, D. P.; Bateman, S. A.; Martin, R. F.; Reum, M. E.; Rose, M.; Whittaker, A. R. D. Aust. J. Chem. 1994, 47, 247-262.
28. (a) White, S.; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B. Nature 1998, 391, 468-471.
29. (b) Kielopf, C. L.; White, S.; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B.; Rees, D. C. Science 1998, 282, 111-115.
30. (c) Dervan, P. B.; Bürlj, R. W. Curr. Opin. Chem. Biol. 1999, 3, 688-693.
31. Singh, A. K.; Lown, J. W. Anti-Cancer Drug Design 2000, 15, 263-275.
32. Mazurov, A. Bioorg. Med. Chem. Lett. 2000, 10, 67-70.
33. All the microwave assisted polymer-supported reactions described here were performed in CEM Discover Microwave System at a frequency of 2450 Hz (0- 300 W). Domestic microwave oven has been used to prepare polymer bound intermediate 4: Bendale, P. M.; Sun, C. M. J. Comb. Chem. 2002, 4, 359-361.
34. Morita, S.; Kitano, K.; Matsubara, J.; Ohtani, T.; Kawano, Y.; Otsubo, K.; Uchida, M. Tetrahedron 1998, 54, 4811-4818.
35. 2: m/z 481.2478. Found 481.2467.