Synthesis and biological evaluation of 1′-C-cyano-pyrimidine nucleosides

Nucleosides and Nucleotides

Volumn 15, Issue 1-3, 1996, Pages 305-324

  Yoshimura, Yuichi ^a   Kano, Fumitaka ^a   Miyazaki, Shuichi ^a   Ashida, Noriyuki ^a   Sakata, Shinji ^a   Haraguchi, Kazuhiro ^b   Itoh, Yoshiharu ^b   Tanaka, Hiromichi ^b   Miyasaka, Tadashi ^b  

^a YAMASA CORPORATION   (Japan)

^b SHOWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1' CYANOCYTARABINE; ANTINEOPLASTIC AGENT; CYTARABINE; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CELL STRAIN KB; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS 1; HUMAN; HUMAN CELL; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029972727     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319608002386     Document Type: Article

References (38)

1. a) Keating, M. J.; McCredie, K. B.; Bodey, G. P.; Smith, T. L.; Gehan, E.; Freidreich, E. J. JAMA 1982, 248, 2481-2486.
2. b) Livingston, R. B.; Carter, S. K. Cancer Chemother. Rep., Part 3 1968, 1 (No.1), 179-205.
3. c) Elison, R. R.; Holland, J. F.; Weil, M.; Jacquillant, C.; Bernard, J.; Sawitsky, A.; Rosner, F.; Gussoff, B.; Silver. R. T.; Karanas, A.; Cuttner, J.; Spurr, C. L.; Hayes, D. M.; Blom, J.; Leone, L. A.; Haurani, F.; Kyle, R.; Huchison, J. L.; Forcier, R. J.; Moon, J. H. Blood 1968, 32, 507-523.
4. a) Fischl, M. A.; Richmann, D. D.; Grieco, M. H.; Gottlieb, M. S.; Volberding, P. A.; Laskin, O. L.; Leedom, J. M.; Groopman, J. E.; Mildvan, D.; Schooley, R. T.; Jackson, G. G.; Durack, R. T.; King, D. New Engl. J. Med. 1987, 317, 185-191.
5. b) Mitsuya, H.; Weinhold, K. J.; Furman, P. A.; St. Clair, M. H.; Lehrman, S. N.; Gallo, R. C.; Bolognesi, D. P.; Barry, D. W.; Broder, S. Proc. Natl. Acad. Sci. U. S. A. 1985, 82, 7096-7100.
6. Yarchoan, R.; Mitsuya, H.; Thomas, R. V.; Pluda, J. M.; Hartman, N. R.; Perno, C.-F.; Marczyk, S.; Allain, J.-P.; Johns, D. G.; Broder, S. Science 1989, 245, 412-415.
7. Yarchoan, R.; Perno, C.-F.; Thomas, R. V.; Klecker, R. W.; Allain, J. P.; Wills, R. J.; McAtee, N.; Fischl, M. A.; Dubinsky, R.; McNeely, M. C.; Mitsuya, H.; Pluda, J. M.; Lawley, T. J.; Leuther, M.; Safai, B.; Collins, J. M.; Myers, C. E.; Brooder, S. Lancet 1988, I, 76-81.
8. a) Hamamoto, Y.; Nakashima, H.; Matsui, T.; Matsuda, A.; Ueda, T.; Yamamoto, N. Antimicrob. Agents Chemother. 1987, 31, 907-910.
9. b) Balzarini, J.; Kang, G.-J.; Dalal, M.; Herdewijn, P.; De Clercq, E.; Broder, S.; John, D. G. Mol. Pharmacol. 1987, 32, 162-167.
10. c) Lin, T.-S.; Schinazi, R. F.; Prusoff, W. H. Biochem. Pharmacol. 1987, 36, 2713-2718.
11. a) Matsuda, A.; Nakajima, Y.; Azuma, A.; Tanaka, M.; Sasaki, T. J. Med. Chem. 1991, 34, 2917-2919.
12. b) Tanaka, T.; Matsuda, A.; Terao, T.; Sasaki, T. Cancer Lett. 1992, 64, 67-74.
13. c) Azuma, A.; Nakajima, Y.; Nishizono, N.; Minakawa, N.; Suzuki, M.; Hanaoka, K.; Kobayashi, T.; Tanaka, M.; Sasaki, T.; Matsuda, A. J. Med. Chem., 1993, 36, 4183-4189.
14. a) Matsuda, A.; Satoh, M.; Nakashima, H.; Yamamoto, N.; Ueda, T. Heterocycles 1988, 27, 2545-2548.
15. b) Calvo-Mateo, A.; Camarasa, M.-J.; Diaz-Ortiz, A.; De las Heras, F. G., Tetrahedron lett. 1988, 29, 941-944.
16. c) Camarasa, M.-J.; Diaz-Ortiz, A.; Calvo-Mateo, A.; De las Heras, F. G.; Balzarini, J.; De Clercq, E. J. Med. Chem., 1993, 32, 1732-1738.
17. d) Fleet, G. W. J.; Son, J. G.; Derome, A. E. Tetrahedron 1988, 44, 625-636.
18. O-Yang, C.; Wu, H. Y.; Fraser-Smith, E. B.; Walker, K. A. M. Tetrahedron Lett., 1992, 33, 37-40.
19. Prisbe, E. J.; Maag, H.; Verheyden, J. P. H.; Rydzewski, R. M., in Nucleosides and Nucleotides as Antitumor and Antiviral Agents, Chu, C. K.; Baker, D. C. Eds.; Plenum Publishing Co., New York, 1993, pp. 101-113.
20. Prisbe, E. J.; Smejkal, J.; Verhyden, J. P. H.; Moffat, J. G. J. Org. Chem. 1976, 41, 1836-1846.
21. a) Hrebabecky, H.; Farkas, J. Collection Czechoslov. Chem. Commun. 1974, 39, 1098-1106.
22. b) Hrebabecky, H.; Farkas, J.: Sorm, F. Collection Czechoslov. Chem. Commun. 1972, 37, 2059-2065.
23. Hayakawa, H.; Miyazawa, M.; Tanaka, H.; Miyasaka, T. Nucleosides Nucleotides 1994, 13, 297-308.
24. a) Holy, A., Nucleic Acids Res. 1974, 1, 289-298.
25. b) Yoshimura, Y.; Ueda, T.; Matsuda, A., Tetrahedron Lett. 1991, 32, 4559-4552.
26. c) Yoshimura, Y.; Otter, B. A.; Ueda, T.; Matsuda, A. Chem. Pharm. Bull. 1992, 40, 1761-1769.
27. a) Haraguchi, K.; Itoh, Y.; Tanaka, H.; Yamaguchi, K.; Miyasaka, T. Tetrahedron Lett. 1993, 34, 6913-6916.
28. b) Itoh, Y.; Haraguchi, K.; Tanaka, H.; Gen, E.; Miyasaka, T. J. Org. Chem. 1995, 60, 656-662.
29. Divakar, K. J.; Reese, C. B. J. Chem. Soc. Perkin Trans. 1 1982, 1171-1176.
30. Removal of silyl protecting group using ammonium fluoride in methanol has been reported : Zhang, W.; Robins, M. J. Tetrahedron Lett. 1992, 33, 1177-1180.
31. Asakura, J.; Robins, M. J. J. Org. Chem. 1990, 55, 4928-4933.
32. Hirota, K.; Kitade, Y.; Kanbe, Y.; Isobe, Y.; Maki, Y. Synthesis 1993, 213-215.
33. a) Robins, M. J.; Trip, E. M. Tetrahedron Lett., 1974, 3369-3372.
34. b) Haraguchi, K.; Tanaka, H.; Maeda, H.; Itoh, Y.; Saito, S.; Miyasaka, T. J. Org. Chem. 1991, 56, 5401-5408.
35. Saenger, W. Principles of Nucleic Acid Structure, Springer-Verlag New York, 1984.
36. Hansen, M. B.; Nielsen, S. E.; Berg., K. J. Immunol. Meth, 1989, 119, 203-210.
37. Ashida, N.; Asano, S.; Kohda, K. Anticancer Res. 1994, 14, 2061-2062.
38. Machida, H.; Sakata, S.; Ashida, N.; Takenuki, K.; Matsuda, A. Antiviral. Chem. Chemother. 1993, 4, 11-17.