One-pot reductive cyclization to antitumor quinazoline precursors

Arkivoc

Volumn 2008, Issue 2, 2008, Pages 33-42

  Kundu, Sandip K ^a   Mahindaratne, Mathew P D ^a   Quintero, Maritza V ^a   Bao, Ande ^b   Negrete, George R ^a  

^a UNIVERSITY OF TEXAS AT SAN ANTONIO   (United States)

^b UNIVERSITY OF TEXAS HEALTH SCIENCE CENTER AT SAN ANTONIO   (United States)

Author keywords

Cancer therapeutics; Indium(III) acetate; Nitro reduction; Quinazolinone; Reductive heterocyclization

Indexed keywords

EID: 38349112023     PISSN: 1551-7012     EISSN: 15517012     Source Type: Journal    
DOI: 10.3998/ark.5550190.0009.205     Document Type: Article

References (40)

1. Himmelsbach, F.; Langkopf, E.; Jung, B.; Blech, S.; Solca, F. U.S. Patent 6 403 580, 2002; Chem. Abstr. 2002, 136, 216716.
2. (a) Traxler P. M. Expert Opinion on Therapeutic Patents 1997, 7, 571-588.
3. (b) Traxler P. M. Ibid. 1998, 8, 1599-1625.
4. (a) Bridges, A. J. Chem. Rev. 2001, 101, 2541.
5. (b) Morin, M. J. Oncogene 2000, 19, 6574.
6. Wakeling, A. E. In Inhibitors of Protein Kinases and Protein Phosphatases - Handbook of Experimental Pharmacology; Vol. 167; Pinna, L. A.; Cohen, P. T. W., Eds.; Springer-Verlag: Berlin, Germany, 2005; pp 433-450.
7. (a) Collins, I.; Workman, P. Curr. Signal Transduc. Ther. 2006, 1, 13.
8. (b) Grünwald, V.; Hidalgo, M. J. Natl. Cancer Inst. 2003, 95, 852.
9. (c) Denny, W. A. Farmaco 2001, 56, 51.
10. (d) Wakeling, A. E.; Barker, A. J.; Davies, D. H.; Brown, D. S.; Green, L. R.; Cartlidge, S. A.; Woodburn, J. R. Breast Cancer Res. Treat. 1996, 38, 67.
11. (a) Wakeling, A. E. Endocr. Relat. Cancer 2005, 12, S183.
12. (b) Wedge, S. R.; Kendrew, J.; Hennequin, L. F.; Valentine, P. J.; Barry, S. T.; Brave, S. R.; Smith, N. R.; James, N. H.; Dukes, M.; Curwen, J. O.; Chester, R.; Jackson, J. A.; Boffey, S. J.; Kilburn, L. L.; Barnett, S.; Richmond, G. H. P.; Wadsworth, P. F.; Walker, M.; Bigley, A. L.; Taylor, S. T.; Cooper, L.; Beck, S.; Jürgensmeier, J. M.; Ogilvie, D. J. Cancer Res. 2005, 65, 4389.
13. (c) Rich, J. N.; Reardon, D. A.; Peery, T.; Dowell, J. M.; Quinn, J. A.; Penne, K. L.; Wikstrand, C. J.; van Duyn, L. B.; Dancey, J. E.; McLendon, R. E.; Kao, J. C.; Stenzel, T. T.; Rasheed, B. K. A.; Tourt-Uhlig, S. E.; Herndon, J. E., II; Vredenburgh, J. J.; Sampson, J. H.; Friedman, A. H.; Bigner, D. D.; Friedman, H. S. J. Clin. Oncol. 2004, 22, 133.
14. (d) Xia, W.; Mullin, R. J.; Keith, B. R.; Liu, L.-H.; Ma, H.; Rusnak, D. W.; Owens, G.; Alligood, K. J.; Spector, N. L. Oncogene 2002, 21, 6255.
15. (e) Wedge, S. R.; Ogilvie, D. J.; Dukes, M.; Kendrew, J.; Chester, R.; Jackson, J. A.; Boffey, S. J.; Valentine, P. J.; Curwen, J. O.; Musgrove, H. L.; Graham, G. A.; Hughes, G. D.; Thomas, A. P.; Stokes, E. S. E.; Curry, B.; Richmond, G. H. P.; Wadsworth, P. F.; Bigley, A. L.; Hennequin, L. F. Cancer Res. 2002, 62, 4645.
16. (a) Bridges, A. J.; Zhou, H.; Cody, D. R.; Rewcastle, G. W.; McMichael, A.; Showalter, H. D. H.; Fry, D. W.; Kraker, A. J.; Denny, W. A. J. Med. Chem. 1996, 39, 267.
17. (b) Fry, D. W.; Kraker, A. J.; McMichael, A.; Ambroso, L. A.; Nelson, J. M.; Leopold, W. R.; Connors, R. W.; Bridges, A. J. Science 1994, 265, 1093.
18. Herget, T.; Freitag, M.; Morbitzer, M.; Kupfer, R.; Stamminger, T.; Marschall, M. Antimicrob. Agents Chemother. 2004, 48, 4154.
19. Bartroli, J.; Turmo, E.; Algueró, M.; Boncompte, E.; Vericat, M. L.; Conte, L.; Ramis, J.; Merlos, M.; García-Rafanell, J.; Forn, J. J. Med. Chem. 1998, 41, 1869.
20. Alagarsamy, V.; Rajasolomon, V.; Meena, R.; Ramseshu, K. V. Biol. Pharm. Bull. 2005, 28, 1091.
21. (a) von Niementowski, S. J. Prakt. Chem. 1895, 51, 564.
22. (b) Hisano, T. Org. Prep. Proced. Int. 1973, 5, 145.
23. (c) Katrizky, A. R.; Rees, C. W.; Scriven, E. F. V. Comprehensive Heterocyclic Chemistry II, Pergamon Press: Oxford, United Kindom, 1996.
24. (d) Armarego, W. L. F. Adv. Heterocycl. Chem. 1979, 24, 1.
25. For example, (a) a reductive cyclocondensation has been reported en route to related diaza heterocycles incorporating sulphonamide unit: Restrepo, J.; Perez, Y.; Salazar, J.; Charris, J.; Arvelo, F.; Lopez, S. E. Heterocycl. Commun. 2006, 12, 341.
26. (b) microwave has been applied in place of thermal Niementowski cyclization: Alexandre, F.-R.; Berecibar, A.; Besson, T. Tetrahedron Lett. 2002, 43, 3911.
27. Matsuno, K; Ushiki, J; Seishi, T; Ichimura, M; Giese, N. A.; Yu, J.-C.; Takahashi, S; Oda, S; Nomoto, Y J. Med. Chem. 2003, 46, 4910.
28. LeMahieu, R. A.; Carson, M.; Nazon, W. C.; Parrish, D. R.; Welton, A. F.; Baruth, H. W.; Yaremko, B. J. Med. Chem. 1983, 26, 420.
29. Sathornsumetee, S.; Rich, J. N. Drugs of Today 2006, 42, 657.
30. Wedge, S. R.; Ogilvie, D. J.; Dukes, M.; Kendrew, J.; Curwen, J. O.; Hennequin, L. F.; Thomas, A. P.; Stokes, E. S. E.; Curry, B.; Richmond, G. H. P.; Wadsworth, P. F. Cancer Res. 2000, 60, 970.
31. Wakeling, A. E.; Guy, S. P.; Woodburn, J. R.; Ashton, S. E.; Curry, B. J.; Barker, A. J.; Gibson, K. H. Cancer Res. 2002, 62, 5749.
32. For transition metal complex-catalyzed reductive heterocyclization see: Akazome, M.; Kondo, T.; Watanabe, Y. J. Org. Chem. 1993, 58, 310.
33. (b) Akazome, M.; Yamamoto, J.; Kondo, T.; Watanabe, Y. J. Organometallic Chem. 1995, 494, 229.
34. (a) Liu, X.; Lu, S. J. Molecular Catalysis A: Chemical 2004, 212, 127.
35. (b) Miyata, T.; Kondo, K.; Murai, S.; Hirashima, T.; Sonoda, N. Angew. Chem. 1980, 92, 1040.
36. (a) Yasuda, K. Nippon Kagaku Zasshi 1967, 88, 749;
37. Chem. Abstr. 1967, 69, 10027.
38. (b) Harada, K. Nature 1967, 214, 479.
39. (c) Kakumoto, T.; Saito, K.; Imamura, A. J. Phys. Chem. 1985, 89, 2286.
40. Bogert, M. T.; Geiger, G. A. J. Am. Chem. Soc. 1912, 34, 524.