Fluorinated nucleosides

Carbohydrate Research

Volumn 327, Issue 1-2, 2000, Pages 87-105

  Pankiewicz, Krzysztof W ^a  

^a PHARMASSET INC   (United States)

Author keywords

Anticancer; Antiviral; Fluorinated nucleosides; Fluorinated sugars

Indexed keywords

3' DEOXY 3' FLUOROADENOSINE; 3' DEOXY 3' FLUOROGUANOSINE; 3' FLUOROTHYMIDINE; 5 ETHYL 2' FLUOROURACIL ARABINOSIDE; 5' O TOXYL 2',3' O ISOPROPYLIDENEADENOSINE; ACICLOVIR; ANTIRETROVIRUS AGENT; ARISTEROMYCIN; CARBODINE; CLEVUDINE; CYCLARADINE; CYTARABINE DERIVATIVE; DIDANOSINE; FIACITABINE; FIALURIDINE; FLUDARABINE; GANCICLOVIR; GEMCITABINE; GUANOSINE DERIVATIVE; IDOXURIDINE; IDOXURIDINE DERIVATIVE; NEPLANOCIN A; NUCLEOCIDIN; NUCLEOSIDE DERIVATIVE; ORGANOFLUORINE DERIVATIVE; RIBAVIRIN DERIVATIVE; THYMIDINE DERIVATIVE; THYMINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; URIDINE DERIVATIVE; VIDARABINE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; CHEMICAL REACTION; CLINICAL TRIAL; DRUG INDICATION; DRUG SCREENING; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORINATION; HUMAN; LACTIC ACIDOSIS; LIVER FAILURE; NEUROTOXICITY; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; REVIEW; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; FLUORINE; NUCLEOSIDES;

EID: 0034631778     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(00)00089-6     Document Type: Review

References (98)

1. Tsuchiya T. Adv. Carbohydr. Chem. Biochem. 48:1990;91-278.
2. D.E. Bergstrom, D.J. Swartling, in J.F. Libeman, A. Greenberg, W.R. Dolbier Jr. (Eds.), Fluorine Containing Molecules, Structure, Reactivity, and Applications, VCH, New York, 1988, pp. 259-308 (Chapter 11).
3. Herdewijn P., Van Aerschot A., Kerremans L. Nucleosides Nucleotides. 8:1989;65.
4. Pankiewicz K.W., Watanabe K.A. J. Fluorine Chem. 64:1993;15-36.
5. Watanabe K.A., Reichman U., Hirota K., Lopez C., Fox J.J. J. Med. Chem. 22:1979;21-24.
6. Etzold G., Hintsche R., Kowollik G., Langen P. Tetrahedron. 27:1971;2463.
7. Hertel L.W., Kroin J.S., Misner J.W., Tustin J.M. J. Org. Chem. 53:1988;2406-2409.
8. C. Thibaudeau, N. Nishizono, Y. Sumita, A. Matsuda, J. Chattopadhyaya, Nucleosides Nucleotides, 18 (1999) 1035-1053, and references therein.
9. Marquez V.E., Lim B.B., Barchi J.J., Nicklaus M.C. Chu C.K., Baker D.C. Nucleosides and Nucleotides as Antitumor and Antiviral Agents. 1993;265-284 Plenum, New York.
10. G.M. Blackburn, D.E. England, F. Kolkmann, J. Chem. Soc., Chem. Commun., (1981) 930-932.
11. Codington J.F., Doerr I., Van Praag D., Bendich A., Fox J.J. J. Am. Chem. Soc. 83:1961;5030-5031.
12. Codington J.F., Doerr I., Van Praag D., Bendich A., Fox J.J. J. Org. Chem. 29:1964;558-564.
13. Wright J.A., Taylor N.F. Carbohydr. Res. 6:1968;347.
14. Wright J.A., Taylor N.F., Fox J.J. J. Org. Chem. 34:1969;2632-2636.
15. Wright J.A., Wilson D.P., Fox J.J. J. Med. Chem. 13:1970;269-272.
16. Robins M.J., Fourun Y., Mengel R. J. Org. Chem. 39:1974;1564.
17. Reichman U., Watanabe K.A., Fox J.J. Carbohydr. Res. 42:1975;233-240.
18. Prusoff W.H. Biochem. Biophys. Acta. 32:1959;296-297.
19. C.H. Tann, P.R. Brodfuehrer, S.P. Brundidge, Sapino Jr., H.G. Howell, J. Org. Chem., 50 (1985) 3644-3647.
20. Martin J.A., Bushnell D.J., Duncan I.B., Dunsdon S.J., Hall M.J., Machin P.J., Merrert J.H., Parkes K.E.B., Roberts N.A., Thomas G.J., Galpin S.A. J. Med. Chem. 33:1990;2137-2145.
21. Sterzycki R.Z., Ghazzouli I., Brenkovan V., Martin J.C., Mansuri M.M. J. Med. Chem. 33:1990;2150-2157.
22. Huang J.-T., Chen L.-C., Wang L., Kim M.-H., Warshaw J.A., Armstrong D., Zhu Q.-Y., Chou T.-C., Watanabe K.A., Matulic-Adamic J. J. Med. Chem. 34:1991;1640.
23. Van Aerschot A., Balzarini J., Pauwels R., Kerremans L., De Clerq E., Herdewijn P. Nucleosides Nucleotides. 8:1989;1121.
24. K.W. Pankiewicz, B. Nawrot, H. Gadler, R.W. Price, K.A. Watanabe, J. Med. Chem., 30 (1987) 2314-2316.
25. Sochacka E., Nawrot B., Pankiewicz K.W., Watanabe K.A. J. Med. Chem. 33:1990;1995-1999.
26. Pankiewicz K.W., Watanabe K.A. Chem. Pharm. Bull. 35:1987;4494-4497.
27. K. Biggadike, A. Borthwick, A.M. Exall, B.E. Kirk, R.A. Ward, J. Chem. Soc., Chem. Commun., (1988) 898-900.
28. K. Biggadike, A.D. Borthwick, D. Evans, A.M. Exall, B.E. Kirk, S.M. Roberts, L. Stephenson, P. Youds, A.M.Z. Slawin, D.J. Williams, J. Chem. Soc., Chem. Commun., (1987) 251-254.
29. Borthwick A., Evans D.N., Kirk B.E., Biggadike K., Exall A.M., Youds P., Roberts S.M., Knight D.J., Coates J.A.V. J. Med. Chem. 33:1990;179-186.
30. Vemishetti P., Saibaba R., Panzica R.P., Abushanab E. J. Med. Chem. 33:1990;681-686.
31. Chu C.K., Matulic-Adamic J., Huang J.-T., Chou T.-C., Burchenal J.H., Fox J.J., Watanabe K.A. Chem. Pharm. Bull. 37:1989;336-339.
32. Marquez V.E., Tseng C.K.-H., Mitsuya H., Aoki S., Kelley J.A., Ford H. Jr., Roth J.S., Broder S., Johns D.G., Driscoll J.S. J. Med. Chem. 33:1990;978-985.
33. Krzeminski J., Nawrot B., Pankiewicz K.W., Watanabe K.A. Nucleosides Nucleotides. 10:1991;781-798.
34. S. Uesugi, H. Niki, M. Ikehara, H. Iwahashi, Y. Kyogoku, Tetrahedron Lett., (1979) 4073.
35. Pankiewicz K.W., Krzeminski J., Ciszewski L.A., Ren W.-Y., Watanabe K.A. J. Org. Chem. 57:1992;553-559.
36. Pankiewicz K.W., Krzeminski J., Watanabe K.A. J. Org. Chem. 57:1992;7315-7321.
37. Maruyama T., Takamatsu S., Kozai S., Satoh Y., Izawa K. Chem. Pharm. Bull. 47:1999;966-970.
38. Siddiqui M.A., Driscoll J.S., Marquez V.E. Tetrahedron Lett. 39:1998;1657-1660.
39. Jeong L.S., Niclaus M.C., George C., Marquez V.E. Tetrahedron Lett. 35:1994;7569-7572.
40. Jeong L.S., Niclaus M.C., George C., Marquez V.E. Tetrahedron Lett. 35:1994;7573-7576.
41. Abbruzzese J.L., Schmidt S., Raber M.N., Levy J.K., Castellanos A.M., Legha S.S., Krakoff I.H. Invest. New Drugs. 7:1989;195-201.
42. McKenzie R., Fried M.W., Sallie R., ConJee Varam H., Di Bisceglie A.M., Park Y., Savararese B., Kleiner D., Tsokos M., Luciano C., Pruett T., Stotka J.L., Straus S.E., Hoofnagle J.H. N. Engl. J. Med. 333:1995;1099-1105.
43. Ma T., Pai S.B., Zhu Y.L., Lin J.S., Shanmuganathan K., Du J., Wang C., Kim H., Newton M.G., Cheng Y.C., Chu C.K. J. Med. Chem. 39:1996;2835-2843.
44. Du J., Choi Y., Lee K., Chun B.K., Hong J.H., Chu C.K. Nucleosides Nucleotides. 18:1999;187-195.
45. Ma T., Lin J.S., Newton M.G., Cheng Y.C., Chu C.K. J. Med. Chem. 40:1997;2750-2754.
46. Lee K., Choi Y., Gullen E., Schleuter-Writz S., Schinazi R.F., Cheng Y.C., Chu C.K. J. Med. Chem. 42:1999;1320-1328.
47. Kois P., Watanabe K.A. Nucleic Acids Symp. Ser. 29:1993;215-216.
48. Kois P., Tocik Z., Spassova M., Ren W.Y., Rosenberg I., Farras Soler J., Watanabe K.A. Nucleosides Nucleotides. 12:1993;1093-1109.
49. Rosenberg I., Farras Soler J., Tocik Z., Ren W.Y., Ciszewski L.A., Kois P., Pankiewicz K.W., Spassova M., Watanabe K.A. Nucleosides Nucleotides. 12:1993;381-401.
50. Kawasaki A.M., Casper M.D., Freier S.M., Lesnik E.A., Zounes M.C., Cummins L.L., Gonzales C., Cook P.D. J. Med. Chem. 36:1993;831-841.
51. Damha M.J., Wilds C.J., Noronha A., Brukner I., Borkow G., Arion D., Parniak M.A. J. Am. Chem. Soc. 120:1998;12976-12977.
52. Stivers J.T., Pankiewicz K.W., Watanabe K.A. Biochemistry. 38:1999;952-963.
53. Drohat A.C., Xiao G., Tordova M., Jagadeesh J., Pankiewicz K.W., Watanabe K.A., Gilliland G., Stivers J.T. Biochemistry. 38:1999;11876-11886.
54. Plunkett W., Huang P., Ganghi V. Nucleosides Nucleotides. 16:1997;1261-1270.
55. Gandhi V., Mineishi S., Huang P., Chapman A.J., Young Y., Chen F., Nowak B., Chubb S., Hertel L.W., Plunkett W. Cancer Res. 55:1995;1517-1524.
56. T.S. Chou, P.C. Heath, L.E. Patterson, L.M. Poteet, R.E. Lakin, A.H. Hunt, Synthesis, (1992) 565-570.
57. Xiang Y., Kotra L.P., Chu C.K., Schinazi R.F. Bioorg. Med. Chem. Lett. 7:1995;743-748.
58. Kotra L.P., Xiang Y., Newton M.G., Schinazi R.F., Cheng Y.C., Chu C.K. J. Med. Chem. 40:1997;3635-3644.
59. Herdewijn P., Balzarini J., De Clercq E., Pauwels R., Baba M., Broder S., Vanderhaeghe H. J. Med. Chem. 30:1987;1270.
60. Hartmann H., Vogt M.W., Durno A.G., Hirsch M.S., Hunsmann G., Eckstein F. AIDS Res. Hum. Retrovir. 4:1988;457.
61. Koshida R., Cox S., Harmenberg J., Gilljam G., Wahren B. Antimicrob. Agents Chemother. 33:1989;2083.
62. Balzarini J., Baba M., Pauwels R., Herdewijn P., De Clercq E. Biochem. Pharmcol. 37:1988;2847-2856.
63. Herdewijn P., Pauwels R., Baba M., Balzarini J., De Clercq E. J. Med. Chem. 30:1987;2132.
64. Schroder I., Holmgren B., Oberg M., Lofgren B. Antiviral Res. 37:1998;57-66.
65. Ajmera S., Bapat A.R., Danenberg K., Danenberg P.V. J. Med. Chem. 27:1984;11-14.
66. Bergstrom D.E., Mott A.W., De Clercq E., Balzarini J., Swartling J.D. J. Med. Chem. 35:1992;3369-3372.
67. Maag H., Rydzewski R.M., McRoberts M.J., Crawford-Ruth D., Verheyden J.P.H., Prisbe E.J. J. Med. Chem. 35:1992;1440.
68. Prisbe E.J., Maag H., Verheyden J.P.H., Rydzewski R.M. Chu C.K., Baker D.C. Nucleosides and Nucleotides as Antitumor and Antiviral Agents. 1993;101-113 Plenum, New York.
69. Lin T.S., Zhu J.-L., Dutschman G.E., Cheng Y.-C., Prusoff W.F. J. Med. Chem. 36:1993;353-362.
70. Mikhailopulo I.A., Poopeiko N.E., Pricota T.I., Sivets G.G., Kvasyuk E.I., Balzarini J., De Clercq E. J. Med. Chem. 34:1991;2195-2202.
71. Morizawa Y., Nakayama T., Yasuda A., Uchida K. Bull. Chem. Soc. Jpn. 62:1994;2119-2120.
72. Van Aershot A., Herdewijn P., Jansen G., Cools M., De Clercq E. Antiviral Res. 12:1989;133-150.
73. Smee D.F., Morris J.L.B., Barnard D.L., Van Aerschot A. Antiviral Res. 18:1992;151-162.
74. Torrence P.F., Imai J., Lesiak K., Warrinnier J., Balzarini J., De Clercq E. J. Med. Chem. 26:1983;1674-1678.
75. (a) E.N. Kilinichenko, T.L. Podkopaeva, M. Kelve, M. Saarma, I.A. Michkhailopulo, Biochem. Biophys. Res. Commun., 167 (1990) 20-26.
76. (b) T. Kovacs, A. Pabuccuogulu, K. Lesiak, P.F. Torrence, Bioorg. Chem., 21 (1993) 192-208.
77. Johnson C.R., Bhumaralkar D.R., De Clercq E. Nucleosides Nucleotides. 14:1995;185-194.
78. Borthwick A.D., Biggadike K. Tetrahedron Lett. 33:1992;3237-3240.
79. S.O. Thomas, V.L. Singleton, J.A. Lowery, R.W. Sharpe, L.M. Pruess, J.N. Porter, J.H. Mowat, N. Bohonos, Antibiot. Ann., 716 (1956/1957).
80. Morton G.O., Lancaster J.E., Van Lear G.E., Fulmor W., Meyer W.E. J. Am. Chem. Soc. 91:1969;1535-1537.
81. Jenkins I.D., Verheyden J.P.H., Moffatt J.G. J. Am. Chem. Soc. 98:1976;3346.
82. Owen G.R., Verheyden J.P.H., Moffatt J.G. J. Org. Chem. 41:1976;3010.
83. Hong J.H., Lee K., Choi Y., Chu C.K. Tetrahedron Lett. 39:1998;3443-3446.
84. Lee K., Choi Y., Hong J.H., Schinazi R.F., Chu C.K. Nucleosides Nucleotides. 18:1999;537-540.
85. Sharma M., Li Y.-X., Ledvina M., Bobek M. Nucleosides Nucleotides. 14:1995;1831-1852.
86. Jahn W. Chem. Ber. 98:1965;1705-1708.
87. Halazy S., Ehrhard A., Danzin C. J. Am. Chem. Soc. 113:1991;315.
88. Matulic-Adamic J., Haeberli P., Usman N. J. Org. Chem. 60:1995;2563-2569.
89. Sekiyama T., Hatsuya S., Tanaka Y., Uchiyama M., Ono N., Iwayama S., Oikawa M., Suzuzki K., Okunishi M., Tsuji T. J. Med. Chem. 41:1998;1284-1298.
90. Ashton W.T., Meurer L.C., Cantone C.L., Field A.K., Hannah J., Karkas J.D., Liou R., Patel G.F., Perry H.C., Wagner A.F., Walton E., Tolman R.L. J. Med. Chem. 31:1988;2304-2315.
91. Qiu Y.-L., Zemlicka J. Nucleosides Nucleotides. 18:1999;2285-2300.
92. Townsend L.B., Gudmundsson K.S., Daluge S.M., Chen J.J., Zhu Z., Koszalka G.W., Boyd L., Chamberlain S.D., Freeman G.A., Biron K.K., Drach J.C. Nucleosides Nucleotides. 18:1999;509-519.
93. M.R. Dyson, P.L. Coe, R.T. Walker, J. Chem. Soc., Chem. Commun., (1991) 741-742.
94. Secrist J.A. III, Tiwari K.N., Riordan J.M., Montgomery J.A. J. Med. Chem. 34:1991;2361-2366.
95. Yoshimura Y., Kitano K., Satoh H., Watanabe M., Miura S., Sakata S., Sasaki S., Matsuda A. J. Org. Chem. 61:1996;822-823.
96. Yoshimura Y., Yamada K., Satoh H., Watanabe M., Miura S., Sakata S., Sasaki S., Matsuda A. J. Org. Chem. 62:1997;3140-3152.
97. Jeong L.S., Moon H.R., Yoo S.J., Lee S.N., Chun M.W., Lim Y.H. Tetrahedron Lett. 39:1998;5201-5204.
98. Jeong L.S., Moon H.R., Choi Y.J., Chun M.W., Kim H.O. J. Org. Chem. 63:1998;4821-4825.