Synthesis of phosphonate derivatives of uridine, cytidine, and cytosine arabinoside

Bioorganic and Medicinal Chemistry

Volumn 8, Issue 10, 2000, Pages 2501-2509

  Jung, Kang Yeoun ^a   Hohl, Raymond J ^b   Wiemer, Andrew J ^b   Wiemer, David F ^a  

^a E11 SSH   (United States)

^b UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTARABINE DERIVATIVE; CYTIDINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; URIDINE DERIVATIVE;

ARTICLE; COLUMN CHROMATOGRAPHY; DIASTEREOISOMER; DNA SYNTHESIS; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROLYSIS; HYDROXYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

ANTIMETABOLITES, ANTINEOPLASTIC; CHEMISTRY, ORGANIC; CYTARABINE; CYTIDINE; PHOSPHONIC ACIDS; PYRUVATE KINASE; URIDINE;

EID: 0033811816     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(00)00183-8     Document Type: Article

References (36)

1. Chabner, B. A. Cytidine analogues. In Cancer Chemotherapy: Principles and Practice, 2nd ed. Chabner, B. A.; Longo, D. L., eds. J. B. Lippincott Co., Philadelphia, 1995.
2. Grant S. Advances in Cancer Research. 72:1998;197-233.
3. Owens, J. K.; Shewach, D. S.; Ullman, B.; Mitchell, B. S. Cancer Research, 1992, 52, 2389.
4. (b) Flasshove, M.; Strumberg, D.; Ayscue, L.; Mitchell, B. S.; Tieier, C.; Heit, W.; Seeber, S.; Schutte, J. Leukemia 1993, 8, 780.
5. For some examples of phosphonate analogues of nucleoside phosphates see ref 20 and: (a) Montgomery, J. A.; Laseter, A. G.; Hewson, K. J. Heterocycl. Chem. 1974, 11, 211.
6. (b) Albrecht, H. P.; Jones, G. H.; Moffatt, J. G. Tetrahedron 1984, 40, 79.
7. (c) Padyukova, N. S.; Karpeisky, M. Y.; Kolobushkina, L. I.; Mikhailov, S. N. Tetrahedron Lett. 1987, 28, 3623.
8. For some examples of phosphonate derivatives of nucleoside analogues see: (a) Montgomery, J. A.; Thomas, H. J. J. Med. Chem. 1979, 22, 109.
9. (b) Fuertes, M.; Witkowski, J. T.; Streeter. D. G.; Robins, R. K. J. Med. Chem. 1974, 17, 642.
10. (c) Kim, C. U.; Luh, B. Y.; Martin, J. C. J. Org. Chem. 1991, 56, 2642.
11. (d) Merta, A.; Votruba, I.; Jindrich, J.; Holy, A.; Cihlar, T.; Rosenberg, I.; Otmar, M.; Tchaou, H. Y. Biochem. Pharmacol. 1992, 44, 2067.
12. (e) Secrist, J. A.; Riggs, R. M.; Comber, R. N.; Montgomery, J. G. Nucleosides & Nucleotides 1992, 11, 947.
13. Da Silva A.D., Maria E.J., Blanchard P., Fourrey J.L., Robert-Gero M. Nucleosides & Nucleotides. 17:1998;2175.
14. Jones G.H., Moffatt J.G. J. Am. Chem. Soc. 90:1968;5337.
15. Xu Y., Flavin M.T., Xu Z.Q. J. Org. Chem. 61:1996;7697.
16. Gray S.H., Ainsworth C.F., Bell C.L., Danyluk S.S., MacCoss M. Nucleosides & Nucleotides. 2:1983;43.
17. Ogilvie K.K., Hakimelahi G.H., Proba Z.A., McGee D.P.C. Tetrahedron Lett. 23:1982;1997.
18. Marcuccio S.M., Elmes B.C., Middleton E.J. Nucleosides & Nucleotides. 11:1992;1695.
19. Lalinde N., Tropp B.E., Engle R. Tetrahedron. 14:1983;2369.
20. (a) Blackburn, G. M. Chem. Ind. (London) 1981, 134.
21. (b) Chambers, R. D.; Jaouhari, R.; O'Hagan, D. Tetrahedron 1989, 45, 5101.
22. (c) Nieschalk, J.; O'Hagan, D. J. Chem. Soc., Chem. Commun. 1995, 719.
23. (d) Berkowitz, D. B.; Eggen, M., Shen, Q.; Shoemaker, R. K. J. Org. Chem. 1996, 61 4666.
24. (e) Levy, S. G.; Wasson, D. B.; Carson, D. A.; Cottam, H. B. Synthesis 1996, 843.
25. (f) Wnuk, S. F., Robins, M. J. J. Am. Chem. Soc. 1996, 118, 2519.
26. Cooperman B.S., Chiu N.Y. Biochemistry. 12:1973;1670.
27. Wiemer D.F. Tetrahedron. 53:1997;16609.
28. Sharpless K.B., Amberg W., Bennani Y.L., Crispino G.A., Hartung J., Jeong K.-S., Kwong H.L., Morikawa K., Wang Z.-M., Xu D., Zhang X.-L. J. Org. Chem. 57:1992;2768.
29. (a) Yokomatsu, T.; Yoshida, Y.; Suemune, K.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 365-368.
30. (b) Lohray, B. B., Maji, D. K., Nandanan, E. Indian J. Chem. 1995, 34B, 1023.
31. (c) Yokomatsu, T., Yamagishi, T., Suemune, K., Yoshida, Y., Shibuya, S. Tetrahedron 1998, 54, 767.
32. (a) Kozlowski, J. K.; Rath. N. P.; Spilling, C. D. Tetrahedron 1995, 51 6385.
33. (b) Cermak, D. M.; Du, Y.; Wiemer, D. F. J. Org. Chem. 1999, 64, 388.
34. For application of this strategy to determination of the stereochemistry of an α-hydroxy-β-aminophosphonate see: Wroblewski, A. E.; Piotrowska, D. G. Tetrahedron: Asymmetry 1999, 10, 2037.
35. Hampton A., Perini F., Harper P.J. Biochemistry. 12:1973;1730.
36. Hohl R.J., Larson R.A., Mannickarottu V., Yachnin S. Blood. 77:1991;1064.