Facile synthesis of 5'-deoxy- and 2',5'-dideoxy-6-thiopurine nucleosides by nucleoside phosphorylases

Tetrahedron

Volumn 54, Issue 30, 1998, Pages 8661-8670

  Chae, Whi Gun ^a,b   Chan, Thomas C K ^a,c   Chang, Ching Jer ^a  

^a PURDUE UNIVERSITY   (United States)

^b Catholic University of Daegu   (South Korea)

^c EPIX Medical Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DOXORUBICIN; MERCAPTOPURINE; MERCAPTOPURINE RIBOSIDE; NUCLEOSIDE PHOSPHORYLASE; THIOGUANOSINE; TIOGUANINE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; CELL GROWTH; DRUG MECHANISM; DRUG SYNTHESIS; GROWTH INHIBITION; HUMAN; HUMAN CELL; PRIORITY JOURNAL;

EID: 0032560724     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00476-1     Document Type: Article

References (24)

1. (1) Johnston, P. G.; Takimoto, C. H.; Grem, J. L.; Fidas, P.; Grossbard, M. L.; Chabner, B. A.; Allegra, C. J.; Chu, E. Cancer Chemotherapy and Biological Response Modifiers Annual 17; Pinedo, H. M.; Longo, D. L.; Chabner, B. A., Eds.; Elsevier: Amsterdam, 1997; p1.
2. (2) Bostrom, B.; Erdmann G. Am. J. Pediatr. Hematol. Oncol. 1993, 15, 80.
3. (3) Elion, G. B.; Hitchings, G. H. J. Am. Chem. Soc. 1955, 77, 1676.
4. (4) Dorr, R. T.; Von Hoff, D. H. Cancer Chemotherapy Handbook; Appleton and Lange: Norwalk, Connecticut, 1994; pp 680-685 and pp 893-898.
5. (5) Revankar, G. R.; Hanna N. B.; Imamura, N.; Lewis A. F.; Larson, S. B.; Finch, R. A.; Avery, T.L.; Robins, R. K. J. Med. Chem. 1990, 33, 121.
6. (6) Reist, E. J.; Hart, P. A.; Goodman, L.; Baker, B. R. J. Org. Chem. 1961, 26, 1557.
7. (7) Montgomery, J. A. Med. Res. Rev. 1993, 13, 209.
8. (8) Hori, N.; Uehara, K.; Mikami, Y. Biosci. Biotech. Biochem. 1992, 56, 580.
9. (9) Chapeau, M-C.; Marnett, L. J. Chem. Res. Toxicol. 1991, 4, 636.
10. (10) Utagawa, T.; Morisawa, H.; Yamanaka, S.; Yamazaki, A.; Yoshinaga, F.; Hirose, Y. Agric. Biol. Chem. 1985, 49, 2425.
11. (11) Utagawa, T.; Morisawa, H., Yamanaka, S.; Yamazaki, A.; Hirose, Y. Agric. Biol. Chem. 1985, 49, 2711.
12. (12) Burns, C. L.; St Clair, M. H.; Frick, L. W.; Spector, T.; Averett, D. R.; English, M. L.; Holmes, T. J.; Krenitsky, T. A.; Koszalka, G. W. J. Med. Chem. 1993, 36, 378.
13. (13) Murakami, K.; Shirasaka, T.; Yoshioka, H.; Kojima, E.; Aoki, S.; Ford, Jr. H.; Driscoll, J. S.; Kelley, J. A.; Mitsuya, H. J. Med. Chem. 1991, 34, 1606.
14. (14) Chae, W.-G.; Cauchon, N. S.; Kozlowski, J. F.; Chang, C.-J. J. Org. Chem. 1992, 57, 1002.
15. (15) Van Draanen, N. A.; Koszalka, G. W. Nucleosides Nucleotides 1994, 13, 1679.
16. (16) Pal, S.; Nair, V. Biotechnology Letters 1997, 19, 349.
17. (17) Hennen, W.; Wong, C.-H. J. Org. Chem. 1989, 54, 4692.
18. (18) Martin, D. S. in Metabolism and Action of Anticancer Drugs; Powis, G.; Prough, R. A., Eds.; Taylor & Francis: London, 1987; pp 91-140.
19. (19) Maehara, Y.; Kusumoto, T.; Sakaguchi, Y., Kusumoto, H.; Kido, Y.; Anai, H.; Sugimachi, K. Cancer 1989, 63, 96.
20. (20) Bos, J. L. Cancer Res. 1989, 49, 4682.
21. (21) Lacal, J. C.; McCormick, F. The ras Superfamily of GTPase; CRC Press: Boca Raton, Florida, 1993.
22. (22) Yoakum, G. H.; Lechner, J. F.; Gabrielson, E. W.; Korba, B. E.; Malan-Shibley, L.; Willey, J. C.; Valerio, M. G.; Shamsuddin, A. M.; Trump, B. F.; Harris, C. C. Science 1985, 227, 1174.
23. (23) Chan, T. C. K.; Chang, C.-j.; Koonchanok, N. M.; Geahlen, R. L. Biochem. Biophys. Res. Commun. 1993, 193, 1152.
24. (24) Alley, M. C.; Scudiero, D. A.; Monks, A.; Hursey, M. L.; Czerwinski, M. J.; Fine, D. L.; Abott, B. J.; Mayo, J. G.; Shoemaker, R. H.; Boyd, M. R. Cancer Res. 1988,48, 589.