New fluorinated pyrazol and uracil derivatives: Synthesis and biological activity

ACS Symposium Series

Volumn 1003, Issue , 2009, Pages 182-209

  Fustero, Santos ^a,b   Sanz Cervera, Juan F ^a,b   Simón Fuentes, Antonio ^a   Román, Raquel ^a   Catalán, Silvia ^a   Murguía, Marcelo ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

^b CENTRO DE INVESTIGACIÓN PRÍNCIPE FELIPE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINATED PYRAZOLES; SYNTHETIC STRATEGIES; URACIL DERIVATIVES;

BIOACTIVITY;

EID: 77950311977     PISSN: 00976156     EISSN: 19475918     Source Type: Book Series    
DOI: 10.1021/bk-2009-1003.ch009     Document Type: Conference Paper

References (51)

1. Organo-Fluorine Compounds (Houben-Weyl); Baasner, B.; Hagemann, H.; Tatlow, J. C., Eds; Thieme: Stuttgart-New York, NY, 2000; Vol. E 10 ac.
2. Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J.C., Eds.; Plenum Press: New York, NY, 1994.
3. Schlosser, M. Angew. Chem. Int. Ed. 1998, 37, 1496-1513.
4. New Fluorinating Agents in Organic Synthesis; German, L.; Zemskov, S., Eds.; Springer-Verlag: Berlin, 1989.
5. Lal, G. S.; Pez, G. P.; Pesaresi, R. J.; Prozonic, F. M.; Cheng, H. J. Org. Chem. 1999, 64, 7048-7054.
6. Uneyama, K. Organofluorine Chemistry; Blackwell Publishing: Oxford, 2006.
7. Genin, M.J.; Biles, C.; Keiser, B.J.; Poppe, S.M.; Swaney, S.M.; Tarpley, W.G.; Yagi, Y.; Romero, D.L. J. Med. Chem. 2000, 43, 1034-1040.
8. Guzman-Perez, A.; Wester, R.T.; Allen, M.C.; Brown, J.A.; Buchholz, A.R.; Cook, E.R.; Day, W.W.; Hamanaka, E.S.; Kennedy, S.P.; Knight, D.R.; Kowalczyk, P.J.; Marala, R.B.; Mularski, C.J.; Novomisle, W.A.; Ruggeri, R.B.; Tracey, W.R.; Hill, R.J. Bioorg. Med. Chem. Lett. 2001, 11, 803-807.
9. Ashton, W.T.; Sisco, R.M.; Dong, H.; Lyons, K.A.; He, H.; Doss, G.A.; Leiting, B.; Patel, R.A.; Wu, J.K.; Marsilio, F.; Thornberry, N.A.; Weber, A.E. Bioorg. Med. Chem. Lett. 2005, 15, 2253-2258.
10. Penning, T.D.; Khilevich, A.; Chen, B.B.; Russell, M.A.; Boys, M.L.; Wang, Y.; Duffin, T.; Engleman, V.W.; Finn, M.B.; Freeman, S.K.; Hanneke, M.L.; Keene, J.L.; Klover, J.A.; Nickols, G.A.; Nickols, M.A.; Rader, R.K.; Settle, S.L.; Shannon, K.E.; Steininger, C.N.; Westlin, M.M.; Westlin, W.F. Bioorg. Med. Chem. Lett. 2006, 16, 3156-3161.
11. Gandhale, D.N.; Patil, A.S.; Awate, B.G.; Naik, L.M. Pesticides 1982, 16, 27-28.
12. DeWald, H.A.; Lobbestael, S.; Poschel, B.P.H. J. Med. Chem. 1981, 24, 982-987.
13. Allerton, C.M.N.; Barber, C.G.; Beaumont, K.C.; Brown, D.G.; Cole, S.M.; Ellis, D.; Lane, C.A.L.; Maw, G.N.; Mount, N.M.; Rawson, D.J.; Robinson, CM.; Street, S.D.A.; Summerhill, N.W. J. Med. Chem. 2006, 49, 3581-3594.
14. Terrett, N.K.; Bell, A.S.; Brown, D.; Ellis, P. Bioorg. Med. Chem. Lett. 1996, 6, 1819-1824.
15. Azami, H.; Barrett, D.; Tanaka, A.; Sasaki, H.; Matsuda, K.; Sakurai, M.; Terasawa, T.; Shirai, F.; Chiba, T.; Matsumoto, Y.; Tawara, S. Bioorg. Med. Chem. 2001, 9, 961-982.
16. Marcic, D. Experim. Appl. Acarology 2005, 36, 177-185, and references cited therein.
17. Nonata, N. Agrochem. Jpn. 2003, 83, 17-19, and references cited therein.
18. Murakami, H.; Masuzawa, S.; Takii, S.; Ito, T. Jpn. Patent 2003201280, 2003.
19. Kim, M.; Sim, C.; Shin, D.; Suh, E.; Cho, K. Crop Protect. 2006, 25, 542-548, and references cited therein.
20. Peters, B.; Fitzgerald, C.J. J. Econ. Entomol. 2003, 96, 1828-1831.
21. Sugimoto, K. Agrochem. Jpn. 2002, 80, 14-16.
22. Walia, U.S.; Brar, L.S.; Dhaliwal, B.K. Indian J. Weed Set. 1998, 30, 48-50.
23. Hamper, B.C.; Mao, M.K.; Phillips, W.G. U.S. Patent 5,698,708, 1997.
24. Dryden, M.W.; Denenberg, T.M.; Bunch, S. Veterinary Parasitol. 2000, 93, 69-75.
25. Phillips, J.; Pilato, M.; Wu, T-t. PCT Int. Appl. WO 9,828,277, 1998.
26. Arthur, F.H. J. Econ. Entomol. 2002, 95, 1314-1318.
27. Penning, T.D.; Talley, J.J.; Bertenshaw, S.R.; Carter, J.S.; Collins, P.W.; Docter, S.; Graneto, M.J.; Lee, L.F.; Malecha, J.W.; Miyashiro, J.M.; Rogers, R.S.; Rogier, D.J.; Yu, S.S.; Anderson, G.D.; Burton, E.G.; Cogburn, J. N.; Gregory, S.A.; Koboldt, C.M.; Perkins, W.E.; Seibert, K.; Veenhuizen, A.W.; Zhang, Y.Y.; Isakson, P.C. J. Med. Chem. 1997, 40, 1347-1365.
28. Kees, K.L.; Fitzgerald, J.J.; Steiner, K.E.; Mattes, J.F.; Mihan, B.; Tosi, T.; Mondoro, D.; McCaleb, M.L. J. Med. Chem. 1996, 39, 3920-3928.
29. Hamper, B.C.; Leschinsky, K.L.; Mischke, D.A.; Prosch, S.D. In Asymmetric Fluoroorganic Chemistry. Synthesis, Applications and Future Directions; Ramachandran, P.V., Ed.; ACS Symposium Series 746; American Chemical Society: Washington, DC, 2000; pp 274-275.
30. Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. Synlett 2004, 18-29.
31. Uneyama, K. Organofluorine Chemistry. Blackwell Publishing Ltd.: Oxford, UK. 2006, pp 180-183.
32. Fustero, S.; Román, R.; Sanz-Cervera, J.F.; Simón-Fuentes, A.; Cuñat, A.C.; Murguía, M. J. Org. Chem. 2008, in press.
33. Nucleosides and Nucleotides as Antitumor and Antiviral Agents; Chu, C. K., Baker, D. C., Eds.; Plenum Press: New York, 1993.
34. As examples, see: Tohyama, Y.; Sanemitsu, Y. Eur. Pat. Appl. EP 1122244 A1, 2001.
35. Theodoridis, G.; Crawford, S. D. (FMC Corporation, USA) US 6277847 B1, 2001.
36. Drewes, M.-W.; Andree, R.; Dollinger, M. (Bayer A.-G., Germany) Ger. Offen. DE 19632005 A1, 1998.
37. Koiso, T.; Ono, S.; Kondo, H.; Asada, T. (Dainippon Ink and Chemicals, Inc., Japan) Jpn. Kokai Tokkyo Kono JP 09241245, 1997.
38. Kameswaran, V. (American Cyanamid Co., USA) US 6191275 B1, 2001.
39. Yagi, K.; Akimoto, K.; Mimori, N.; Miyake, T.; Kudo, M.; Arai, K.; Ishii, S. Pest Manag. Sci. 2000, 56, 65-73.
40. Lai, G. S.; Pez, G. P.; Pesaresi, R. J.; Prozonic, F. M ; Cheng, H. J. Org. Chem. 1999, 64, 7048-7054.
41. Kotoris, C. C.; Chen, M.-J.; Taylor, S. J. Org. Chem. 1998, 63, 8052-8057.
42. Middleton, W. J.; Bingham, E. M. J. Org. Chem. 1980, 45, 2883-2887.
43. Fustero, S.; Piera, J.; Sanz-Cervera, J. F.; Catalán, S.; Ramírez de Arellano, C. Org. Lett. 2004, 6, 1417-1420.
44. Fustero, S.; Salavert, E.; Sanz-Cervera, J. F.; Piera, J.; Asensio, A. Chem. Commun. 2003, 844-845.
45. Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823-826
46. Curran, D. P. Angew. Chem. Int. Ed. 1998, 37, 1174
47. Handbook of Fluorous Chemistry, Gladysz, J. A.; Curran, D. P.; Horváth, I. T. (Eds.), Wiley-VCH: Weinheim, 2004.
48. Fustero, S.; Catalán, S.; Flores, S.; Jiménez, D.; del Pozo, C.; Aceña. J. L.; Sanz-Cervera, J. F.; Mérida, S. QSAR Comb. Sci. 2006, 25, 753-760.
49. Fustero, S.; Catalán, S.; Piera, J.; Sanz-Cervera, J. F.; Fernández, B.; Aceña, J. L. J. Org. Chem. 2006, 71, 4010-4013.
50. Greuter, H.; Lang, R. W.; Romann, A. J. Tetrahedron Lett. 1988, 3291-3294.
51. Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vols. 1-3.