Synthesis and antitumor activity of 5-fluorouracil derivatives

Medicinal Research Reviews

Volumn 16, Issue 1, 1996, Pages 51-86

  Ozaki, Shoichiro ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 (OCTYLTHIO)CARBONYL 5 FLUOROURACIL; 1 ACRYLOYLOXYETHYLCARBAMOYL 5 FLUOROURACIL DERIVATIVE; 1 CARBAMOYL 5 FLUOROURACIL; 1 DECANOYLOXYMETHYL 5 FLUOROURACIL; 1 ETHYLTHIOMETHYL 5 FLUOROURACIL; 1 METHYLTHIOMETHYL 5 FLUOROURACIL; 3 (2 TETRAHYDROFURYL) 5 FLUOROURACIL; 5 FLUORO 5' O PENTANOYLURIDINE; ANTINEOPLASTIC AGENT; CARMOFUR; CYCLOPHOSPHAMIDE; CYTARABINE; DAUNORUBICIN; FLUOROURACIL; FLUOROURACIL DERIVATIVE; MERCAPTOPURINE; METHOTREXATE; MITOMYCIN C; POLYVINYL DERIVATIVE; PROCARBAZINE; TEGAFUR; UNCLASSIFIED DRUG;

ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; CANCER GRAFT; DRUG STRUCTURE; DRUG SYNTHESIS; INTRAPERITONEAL DRUG ADMINISTRATION; LEUKEMIA CELL LINE; NONHUMAN; ORAL DRUG ADMINISTRATION; POLYMERIZATION; REVIEW;

ANIMALS; ANTIMETABOLITES, ANTINEOPLASTIC; DRUG SCREENING ASSAYS, ANTITUMOR; FLUOROURACIL; LEUKEMIA L1210; MICE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030064002     PISSN: 01986325     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-1128(199601)16:1<51::AID-MED2>3.0.CO;2-T     Document Type: Review

References (59)

1. R. Duschinski, F. Pleven, and C. Heidelberger, J. Am. Chem. Soc. 79, 4559 (1957).
2. C. Heidelberger, N. K. Chauduri, P. Danneberg, M. Mooren, L. Griesbach, R. Duschinsky, R. J. Schnitzer, E. Pleven, and L. Scheneider, Nature 179, 663 (1957).
3. G. C. Daher, B. E. Harris, R. B. Diasio, Pharmac. Ther. 48, 189 (1990).
4. R. Paegle, M. Lidaks, and Yu. P. Shvachkin, Khim. Geterotstkl. Soedin., Aka. Nauk Latv. SSR 316 (1966).
5. S. A. Hiller, R. A. Zhnk, and M. Lidak. Dokl. Akad. Nauk SSSR 176, 332 (1967).
6. S. A. Hiller, R. A. Zhnk, and G. Ya. Nashatyr, Khim. Geterotsikl. Soedin. 557 (1968); Chem. Abstr. 69, 96641h (1968).
7. S. A. Hiller, R. A. Zhnk, and G. Ya. Nashatyr, Khim. Geterotsikl. Soedin. 557 (1968); Chem. Abstr. 69, 96641h (1968).
8. M. Lidaks, R. Paegle, M. Plata, K. Ya. Pets, and Yu. P. Shvachkin, Khim. Geterotsikl. Soedin., 379, (1968); Chem. Abstr. 69 96640g (1968).
9. M. Lidaks, R. Paegle, M. Plata, K. Ya. Pets, and Yu. P. Shvachkin, Khim. Geterotsikl. Soedin., 379, (1968); Chem. Abstr. 69 96640g (1968).
10. T. T. Sakai, A. L. Pogolotti, and D. V. Santi, J. Heterocycl. Chem. 5, 849 (1968).
11. W. Klotzer, and M. Herberz, Monatsh. Chem. 99, 847 (1968).
12. T. Seita, M. M. Kinoshita, and M. Imoto, Bull. Chem. Soc. Jpn. 46, 1572 (1973).
13. M. Tada, Chem. Lett. 1975, 129.
14. M. Tada, Bull. Chem. Soc. Jpn. 48, 3427 (1975).
15. S. Ozaki, Y. Ike, H. Mizuno, K. Ishikawa, and H. Mori, Bull. Chem. Soc. Jpn. 50, 2406 (1977).
16. S. Ozaki, Y. Watanabe, T. Hoshiko, H. Mizuno, K. Ishikawa, and H. Mori, Chem. Pharm. Bull. 32, 733 (1984).
17. S. Ahmad, S. Ozaki, T. Nagase, M. Iigo, R. Tokuzen, and A. Hoshi, Chem. Pharm. Bull. 35, 4137 (1987).
18. T. Hoshiko, S. Ozaki, Y. Watanabe, T. Ogasawara, Y. Yamaguchi, K. Fujiwara, A. Hoshi, and M. Iigo, Chem. Pharm. Bull. 33, 2832 (1985).
19. S. Ozaki, Y. Watanabe, T. Hoshiko, T. Nagase, T. Ogasawara, H. Furukawa, A. Uemura, K. Ishikawa, H. Mori, A. Hoshi, M. Iigo, and R. Tokuzen, Chem. Pharm. Bull. 34, 150 (1986).
20. T. Nagase, K. Shiraishi, Y. Yamada, and S. Ozaki, Heterocycles 27, 1155 (1988).
21. S. Ozaki, J. Ohnishi, Y. Watanabe, T. Nohda, T. Nagase, T. Akiyama, N. Uehara, and A. Hoshi, Polymer J. 21, 955 (1989).
22. S. Ozaki, J. Ohnishi, Y. Watanabe, T. Nohda, T. Nagase, T. Akiyama, N. Uehara, and A. Hoshi, Polymer J. 21, 955 (1989).
23. (a) A. Hoshi, M. Iigo, A. Nakamura, M. Yoshida, and K. Kuretani, Gann 67, 725 (1976).
24. (b) A. Hoshi, M. Iigo, A. Nakamura, M. Inomata, K. Kuretani, Chem. Pharm. Bull. 26, 161 (1978).
25. Mitsui Pharmaceutical, Inc., and Mitsui Toatsu Chemicals, Inc., Japan Patent Open, 50-148365 (1975); Japan Patent 60-7625; U.S.P. 4071519 (1978). German Patent Open, 2455423 (1975), 2639135 (1977); Belg. Patent 846955 (1977).
26. S. Ozaki, Chem. Rev. 72, 457 (1972).
27. M. Iigo, A. Hoshi, A. Nakamura, and K. Kuretani, Cancer Chemother. Pharmacol. 1, 203 (1978).
28. a) Y. Koyama, Gun To Kagakuryoho 7, 1181 (1980).
29. b) M. Nakanishi, Y. Tsutanishi, T. Nakamura, I. Hashimoto, Y. Sawata, M. Kawai, T. Okuno, S. Fujisawa, and M. Taneda, Yakuri To Chiryo 8, 1211 (1980).
30. M. Iigo, A. Hoshi, M. Inomata, N. Andoh, and K. Kuretani, J. Pharm. Dyn. 4, 203 (1981).
31. Mitsui Toatsu Chemicals Inc., Japan. Patent Open 51-98280 (1976).
32. Mitsui Toatsu Chemicals Inc., Japan. Patent Open 52-33683 (1977).
33. Mitsui Toatsu Chemicals Inc., Japan. Patent Open 54-12281 (1979).
34. A. Hoshi, M. Inomata, F. Kanzawa, M. Iigo, and K. Kuretani, J. Pharm. Dyn. 3, 208 (1982).
35. Ono Pharmaceuticals, Japan. Patent Open 51-98280 (1976).
36. J. Yamashita, I. Yamawaki, S. Ueda, M. Yasumoto, N. Unemi, and S. Hashimoto, Chem. Pharm. Bull. 30, 4258 (1982).
37. Mitsui Toatsu Chemicals Inc., Japan. Patent Open 51-113882 (1976) [Chem. Abstr. 86, 18993r (1977)].
38. L. R. Lewis, F. Schneider, and R. K. Robins, J. Org. Chem. 26, 3837 (1961).
39. S. Ozaki, Y. Ike, and H. Mori, Mitsui Toatsu Chem. Inc., Japan. Patent Open, 53-2483 (1978) [Chem. Abstr. 89, 24348h (1978)].
40. M. Kurono, Y. Sakai, H. Yokoyama, T. Chiba, and S. Fujii, Ono Pharm. Inc., Japan. Patent Open 53-31674 (1978) [Chem. Abstr. 89, 4349u (1978)].
41. T. Miura, T. Uchiyama, M. Takahashi, K. Yamamoto, S. Koizumi, K. Fukamatsu, and J. Saito, Iyakuhin Kenkyu 11, 73 (1980).
42. T. Hoshiko, S. Ozaki, Y. Watanabe, T. Ogasawara, Y. Yamauchi, K. Fujiwara, A. Hoshi, and M. Iigo, Chem. Pharm Bull. 33, 2832 (1985).
43. T. Hoshiko, Y. Watanabe, and S. Ozaki, Heterocycles 20, 2429 (1983).
44. J. H. Burchenal, V. E. Currie, M. D. Dowling, J. J. Fox, and I. H. Krakoff, Ann. N. Y. Acad. Sci. 255, 202 (1975).
45. B. Drewinko, L. Y. Yang, D. H. W. Ho, J. Benvenuto, T. L. Loo, and E. J. Freireich, Cacer 45, 1144 (1980).
46. J. A. Houghton and P. J. Houghton, ibid. 45, 1159 (1980).
47. M. Saneyoshi, M. Inomata, and F. Fukuoka, Chem. Pharm. Bull. 26, 2990 (1978).
48. S. Shuto, H. Itoh, S. Ueda, S. Imamura, K. Furukawa, M. Tsujino, A. Matsuda, and T. Ueda, Chem. Pharm. Bull. 36, 209 (1988).
49. H. Kawabata, K. Moriguchi, K. Sakai, T. Endo, T. Tsuruo, and H. Satoh, Jpn. J. Cancer Res. 44, 320 (1985).
50. Part of this work has been briefly described in a patent; Japan. Patent Open 63-1965519 (1988) [Chem. Abstr. 110, 11523y (1989)].
51. S. Ozaki, T. Akiyama, Y. Ike, H. Mori, and A. Hoshi, Chem. Pharm. Bull. 37, 3405 (1989).
52. S. Ozaki, T. Akiyama, T. Morita, M. Kumegawa, T. Nagase, N. Uehara, and A. Hoshi, Chem. Pharm. Bull 38, 3164 (1990).
53. K. A. Watanabe, A. Matsuda, M. J. Halat, D. H. Hollenberg, J. S. Nisselbaum, and J. J. Fox, J. Med. Chem. 24, 893 (1981).
54. M. Akashi and K. Takemoto, Advan. Polym. Sci. 97, Springer-Verlag, 107 (1990).
55. M. Akashi, N. Morita, O. Miyauchim, and E. Yashima, New Polym. Mat. 3, 31 (1991).
56. M. Akashi, N. Miyauchi, N. Morita, and T. Minoda, J. Bioactive and Compatible Polym. 2, 232 (1987).
57. T. Ouchi, H. Fujie, S. Jokei, Y. Sakamoto, H. Chiklashita, T. Inoi, and O. Vogl, J. Polm. Sci., Polym. Chem. Ed. 24, 2059 (1986).
58. S. Ozaki, J. Ohnishi, T. Akiyama, T. Nagase, N. Uehara, and A. Hoshi, Polym. J. 22, 689 (1990).
59. F. R. Mayo and F. W. Lewis, J. Am. Chem. Soc. 66, 1594 (1944).