Synthesis and evaluation of new 5-fluorouracil antitumor cell differentiating derivatives

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 3, 2003, Pages 315-323

  Domínguez, José F ^a   Marchal, Juan A ^b   Correa, Antonio ^a   Carrillo, Esmeralda ^b   Boulaiz, Houria ^c   Aránega, Antonia ^c   Gallo, Miguel A ^a   Espinosa, Antonio ^a  

^a UNIVERSITY OF GRANADA   (Spain)

^b UNIVERSITY OF JAÉN   (Spain)

^c UNIVERSITY OF GRANADA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; FLUOROURACIL; FLUOROURACIL DERIVATIVE; METHYL 3 METHOXY 3 (5 FLUOROURACIL 1 YL)PROPANOATE; N,N' BIS[3 METHOXY 3 (5 FLUOROURACIL 1 YL)PROPIONYL] ALPHA,ALPHA' DIAMINO 3 XYLENE; N,N' BIS[3 METHOXY 3 (5 FLUOROURACIL 1 YL)PROPIONYL]ETHYLENEDIAMINE; THYMIDYLATE SYNTHASE; UNCLASSIFIED DRUG;

ARTICLE; CELL DIFFERENTIATION; CELL MATURATION; CELL STRUCTURE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG PURIFICATION; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; GROWTH INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; PHENOTYPE; RHABDOMYOSARCOMA; SARCOMA CELL; STEREOISOMERISM;

ANTINEOPLASTIC AGENTS; CELL DIFFERENTIATION; CELL DIVISION; DRUG SCREENING ASSAYS, ANTITUMOR; FLOW CYTOMETRY; FLUOROURACIL; HUMANS; INTERMEDIATE FILAMENTS; MICROSCOPY, PHASE-CONTRAST; PRODRUGS; RHABDOMYOSARCOMA; STRUCTURE-ACTIVITY RELATIONSHIP; THYMIDYLATE SYNTHASE; TUMOR CELLS, CULTURED;

EID: 0037294428     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(02)00464-9     Document Type: Article

References (51)

1. Pierce G.B., Speers W.C. Cancer Res. 48:1988;1996.
2. Sach L. Cancer Res. 47:1987;1981.
3. (a) Kosugi H., Towatari M., Hatano S., Kitamura K., Kiyoi H., Kinoshita T., Tanimoto M., Murate T., Kawashima K., Saito H., Naoe T. Leukemia. 13:1999;1316
4. (b) Chan T.W., Mark G., Huynh H. Int. J. Oncol. 19:2001;263
5. (c) Tobita T., Takeshita A., Kitamura K., Ohnishi K., Yanagi M., Hiraoka A., Karasuino T., Takendri M., Miyawaki S., Ueda R., Naoé T., Ohno R. Blood. 90:1997;967.
6. (a) Tilly H., Castaigne S., Bordessoule D., Casassus P., LePrise P., Tertian G., Desablends B., Henry-Amar M., Degos L. J. Clin. Oncol. 8:1990;272
7. (b) Marchal J.A., Prados J., Melguizo C., Fernández J.E., Vélez C., Alvarez L., Aránega A. J. Lab. Clin. Med. 130:1997;42.
8. Chen Z.X., Breitman T.R. Cancer Res. 54:1994;3494.
9. Petersen O.W., Ronnov L., Weaver V.M., Bisell M.J. Adv. Cancer Res. 75:1998;135.
10. Makishima M., Honma Y., Hozumi M., Sampi H., Haltori M., Ishikama I., Ogura H., Motoyoshi K. Exp. Hematol. 20:1992;879.
11. Douglas K.T. Med. Res. Rev. 7:1987;441.
12. Perry, M.; Yarbro, J. W. In Toxicity of Chemotherapy; Grune & Atraton Inc.: New York, 1984.
13. (a) Iwasaki T., Nishitani T., Horikawa H., Inoue I. Tetrahedron Lett. 22:1979;2019
14. (b) Hiller S.A.; Zhuk R.A.; Lidak M.; Yu M.; Zidermane A. A.; British Patent 1,168,391, 1968; Chem. Abstr. 1970, 43715c.
15. (c) Cook A.F., Holman M.J., Kramer M.J., Trown P.W. J. Med. Chem. 22:1979;1330.
16. (a) Gallo M.A., Espinosa A., Campos J., Entrena A., Domínguez J.F., Camacho E., Pineda M.J. Synlett. 6:1993;389
17. (b) Ochi K., Miyamoto K., Miura Y., Mitsui H., Matsunaga I., Shindo M. Chem. Pharm. Bull. 33:1985;1703
18. (c) Rosowsky A., Kim S.H., Wick M. J. Med. Chem. 24:1981;1155.
19. Campos J., Pineda M.J., Gómez J.A., Entrena A., Trujillo M.A., Gallo M.A., Espinosa A. Tetrahedron. 52:1996;8907.
20. Marchal J.A., Prados J., Melguizo C., Gómez J.A., Campos J., Gallo M.A., Espinosa A., Arena N., Aránega A. Br. J. Cancer. 79:1999;807.
21. Marchal J.A., Melguizo C., Prados J., Aránega A.E., Gómez J.A., Campos J., Gallo M.A., Espinosa A., Arena N., Aránega A. Jpn. J. Cancer Res. 91:2000;934.
22. Nishitani T., Iwasaki T., Mushika Y., Miyoshi M. J. Org. Chem. 44:1979;2019.
23. (a) Zhou, R.; Fan, Ch.; Zhao, R. Gaodeng Xuexiao Huaxue Xuebao 1986, 7, 508; Chem. Abstr. 1987, 107, 97081r.
24. (a) Zhou, R.; Fan, Ch.; Zhao, R. Gaodeng Xuexiao Huaxue Xuebao 1986, 7, 508; Chem. Abstr. 1987, 107, 97081r.
25. (b) Zhuo, R.; Liu, G.; Peng, P. Gaodeng Xuexiao Huaxue Xuebao 1991, 12, 555-559; Chem. Abstr. 1992, 116, 21442z.
26. (b) Zhuo, R.; Liu, G.; Peng, P. Gaodeng Xuexiao Huaxue Xuebao 1991, 12, 555-559; Chem. Abstr. 1992, 116, 21442z.
27. Chen, Q.; Zhuo, R.; Zhou, N. Wuhan Daxue Xuebao, Ziran Kexueban 1986, 1, 65; Chem. Abstr. 1987, 106, 176329k.
28. Chen, Q.; Zhuo, R.; Zhou, N. Wuhan Daxue Xuebao, Ziran Kexueban 1986, 1, 65; Chem. Abstr. 1987, 106, 176329k.
29. McCormick J.E., McElhinney R.S. J. Chem. Res. 7:1983;176.
30. Chen, Q.; Hu, W. Wuhan Daxue Xuebao, Ziran Kexueban 1987, 3, 89; Chem. Abstr. 1988, 109, 130361h.
31. Chen, Q.; Hu, W. Wuhan Daxue Xuebao, Ziran Kexueban 1987, 3, 89; Chem. Abstr. 1988, 109, 130361 h.
32. Antolovich M., Philips D.J., Rae A.D. Inorg. Chim. Acta. 156:1989;189.
33. (a) Larock, R.C. In Comprehensive Organic Transformations: A Guide to Functional Group Preparations; John Wiley & Sons Inc., VCH: New York, 1989; p 987, and refs. cited therein.
34. (b) Carey F.A.; Sundberg, R.J. In Advanced Organic Chemistry. Part B: Reactions and Synthesis, 3rd Ed.; Plenum Publishers; Plenum: New York, 1990; p 152.
35. (c) March, J. In Advanced Organic Chemistry, 3rd ed.; John Wiley & Sons: 1985; p 339.
36. (d) Feairheller S.H., Bistline R.G., Bilyk A., Dudley R.L., Kozempel M.F., Haas M.J. J. Am. Oil Chem. Soc. 71:1994;863
37. (e) Nagai, M.; Oohashi, Y.; Tsukahara, I.; Shibata, K. Kawamata, A. Jpn Kokay Tokkyo Koho JP 06,135,914; Chem. Abstr. 1994, 121, 280260b.
38. (e) Nagai, M.; Oohashi, Y.; Tsukahara, I.; Shibata, K. Kawamata, A. Jpn Kokay Tokkyo Koho JP 06,135,914; Chem. Abstr. 1994, 121, 280260b.
39. Basha A., Lipton M., Weinreb S.M. Tetrahedron Lett. 48:1977;4171.
40. Yasumoto M., Yamawaki I., Marunaka T., Hashimoto S. J. Med. Chem. 21:1978;738.
41. Ozaki S., Watanabe Y., Hoshiko T., Nagase T., Ogasawara T., Furukawa H., Uemura A., Ishikawi K., Mori H., Iigom M., Tokuzem R. Chem. Pharm. Bull. 34:1986;150.
42. Tanaka F., Fukuse T., Wada H., Fukushima M. Currn. Pharm. Biotechn. 1:2000;137.
43. Zupi G., Marangolo M., Arancia G., Greco C., Laudonio N., Iosi F., Formisano G., Malorni W. Cancer Res. 48:1988;6193.
44. Gundersen G.-C., Khawaja S., Bulinski J.-C. J. Cell Biol. 109:1989;2275.
45. Wijnaendts L.C., Van Der Linden J.C., Van Unnik A.J., Delemarre J.F., Voute P.A., Meijer C.J. J. Pathol. 174:1994;283.
46. Carter R.L., MacCarthy K.P., Machin L.G., Jameson C.F., Philip E.R., Pinkerton C.R. Histopathology. 1:1989;585.
47. Molenaar W.M., Oosterhuis J.W., Oosterhuis A.M., Ramaekers F.C. Human Pathol. 16:1985;838.
48. Lesuffleur T., Kornowski A., Luccioni C., Muleris M., Barbat A., Beaumatin J., Dussaulx E., Sutrillaux B., Zweibaum A. Int. J. Cancer. 49:1991;721.
49. Climie S.M., Santi D.V. Proc. Natl. Acad. Sci. U.S.A. 87:1990;633.
50. Pogolotti, A.L.; Weill, C.; Santi, D.V. Biochemistry, 1979, 13, 2794.
51. MacAllister R.M., Melnyk J., Finklestein J.Z., Adams E.-C., Gardner M.B. Cancer. 24:1969;520.