A general synthetic method of 5-carboranyluracil nucleosides with potential antiviral activity and use in neutron capture therapy

Nucleosides and Nucleotides

Volumn 16, Issue 12, 1997, Pages 2133-2150

  Goudgaon, Naganna M ^a,c   El Kattan, Yahya A ^a,b,c   Xia, Xiaoyang ^b   McAtee, Jeff ^b   Soria, José ^b   Wey, Shiow Jyi ^b   Liotta, Dennis C ^b   Schinazi, Raymond F ^a,c  

^a EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b EMORY UNIVERSITY   (United States)

^c ATLANTA VA MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; CARBORANYL 2' DEOXYURIDINE; CARBORANYL XYLOFURANOSYLURACIL; NUCLEOSIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; FEMALE; GLYCOSYLATION; HERPES SIMPLEX VIRUS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; HUMAN TISSUE; INTRAPERITONEAL DRUG ADMINISTRATION; MALE; MONKEY; MOUSE; NEUTRON CAPTURE THERAPY; NONHUMAN; NUCLEOTIDE METABOLISM; TOXICITY TESTING;

ANIMALIA; HERPES; HUMAN IMMUNODEFICIENCY VIRUS; SIMPLEXVIRUS;

EID: 0031467727     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319708002564     Document Type: Article

References (35)

1. A short communication was published earlier on this subject: El Kattan, Y.; Goudgaon, N. M.; Fulcrand, G.; Liotta, D. C.; Schinazi, R. F. Current Topics in the Chemistry of Boron, Kabalka, G. W. Ed. The Royal Society of Chemistry, England, U.K. 1994, 181-184.
2. Hawthorne, M. F. Angew. Chem., Int. Ed. Engl. 1993, 32, 950-984.
3. Barth, R. F.; Soloway, A. H.; Fairchild, R. G.; Brugger, R. M. Cancer 1992, 70, 2995-3007.
4. Goudgaon, N. M.; Fulcrand El-Kattan, G., Schinazi, R. F. Nucleosides Nudeotides 1994, 13, 849-880.
5. Fairchild, R. G.; Kalef-Erza, J. A.; Saraf, S. K.; Fiarman, G.; Ramsey, E.; Wielopolski, L. Neutron Beam Design, Development and Performance for Neutron Capture Therapy; Harling, O. K.; Bernard, J. A. and Zamenhof, R. G. Eds.; Plenum Press: New York, 1990; Vol. 35; pp 3426-3428.
6. Schinazi, R. F.; Prusoff, W. H. J. Org. Chem. 1985, 50, 841-847.
7. Yamamoto, Y.; Seko, T.; Nemoto, H. J. Org. Chem. 1989, 54, 4734-4736.
8. DeCamp, D. L.; Babé, L. M.; Salto, R.; Lucich, J. L.; Koo, M.-S.; Kahl, S. B.; Craik, C. S. J. Med. Chem. 1993, 35, 3426-3428.
9. Wyzlic, I. M.; Soloway, A. H. Tetrahedron Lett. 1993, 33, 7489-7490.
10. (a) Schinazi, R. F.; Goudgaon, N. M.; Soria, J.; Liotta, D. C. Advances in Neutron Capture Therapy, Soloway, A. H.; Barth, R. F.; Carpenter, D.E., Eds.; Plenum Press: New York and London, 1993; pp 285-288.
11. (b) Fulcrand-El Kattan, G.; Goudgaon, N. M.; Ilksoy, N.; Huang, J-T.; Watanabe, K. A.; Sommadossi, J-P.; Schinazi, R. F. J. Med. Chem. 1994, 37, 2583-2588.
12. Schinazi, R. F.; Keane, T. E.; Liotta, D. C. LIS Patent 5,599,796,1997.
13. Schinazi, R. F.; Goudgaon, N. M.; Fulcrand, G.; El-Kattan, Y.; Lesnikowski, Z.; Ullas, G.; Moravek, J.; Liotta, D. C. Int. J. Rad.iat. Oncol. Biol. Phys. 1994, 28, 1113-1120.
14. For X-ray parameters of carboranes see: Holdbrey, J. D.; Iveson, P. B.; Lockhart, J. C.; Tomkinson, N. P.; Teixidor, F.; Romerosa, A.; Vinas C.; Rius J. J. Chem. Soc. Dalton Trans. 1993, 1451-1461.
15. Prystas, M.; Sorm, F. Collect. Czech. Chem. Commun. 1964, 29, 121-129.
16. (a) Coe, P. L.; Walker, R. T. Nucleosides Nucleotides 1992, 11, 553-555.
17. (b) Kundu, N.G.; Schmitz, S. A. J. Heterocycl. Chem. 1982, 19, 463-464
18. Heying, T. L.; Ager Jr, J. W.; Clark, S. L.; Mangold, D. J.; Goldstein, H. L.; Hillman, M.; Polak, R. J.; Szymanski, J. W. Inorg. Chem. 1963, 2, 1089-1092.
19. Pace, R.J.; Williams, J.; Williams, R. L. J. Chem. Soc. 1961, 2196-2204.
20. Schaeeffer, R. J. Am. Chem. Soc. 1957, 79, 1006-1007.
21. Vorbruggen, H.; Hofle, G. Chem. Ber. 1981, 124, 1256-1268.
22. (a) Schinazi, R. F.; McMillan, A.; Cannon, D.; Mathis, R.; Lloyd, R. M. jr.; Peck, A.; Sommadossi, J.-P.; St. Clair, M.; Wilson, J.; Furman, P.A.; Painter, G.; Choi, W.-B.; Liotta, D. C. Antimicrob. Agents Chemother. 1992, 36, 2423-2431.
23. (b) Furman, P. A.; Davis, M.; Liotta, D. C.; Paff, M.; Frick, L. W.; Nelson, D. J.; Dornsife, R. E.; Wurster, J. A.; Wilson, L. J.; Fyfe, J. A.; Turtle, J. V.; Miller, W. H.; Condreay, L.; Averett, D. R.; Schinazi, R. F.; Painter, G. R. Antimicrob. Agents Chemother. 1992, 36, 2686-2692.
24. Choi, W.-B.; Wilson, L. J.; Yeola, S.; Liotta, D. C.; Schinazi, R. F. J. Am. Chem. Soc. 1991, 213, 9377-9379.
25. Schinazi, R. F.; Liotta, D. C. US Patent 5,405,598, 1995.
26. Van Roey, P.; Pangborn, W. A.; Schinazi, R. F.; Painter, G.; Liotta, D. C. Antiviral Chem. Chemother. 1993, 4, 369-375.
27. (a) Lesnikowski, Z. J.; Schinazi, R. F. J Org. Chem. 1993, 58, 6531-6534.
28. (b) Fulcrand-El Kattan, G., Lesnikowski, Z.J., Yao, S., Tanious, F., Wilson, W. D., and Schinazi, R. F. J. Am. Chem. Soc. 1994, 226:7494-7501.
29. (c) Lesnikowski, Z. L., Fulcrand, G., Lloyd, R.M., Juodawlkis, A.S., and Schinazi, R.F. Biochemistry 1996, 35:5741-5746.
30. Das, B.; Kundu, N. G. J. Chem. Res. Synop. 1992, 11, 364-365.
31. Spector, T.; Porter, D.; Rahim, S.G. U.S. PCT Int. Appl. WO 92 01, 452 06, Feb. 1992.
32. Yamamoto, Y.; Seko, T.; Nakamura, H. Heteroatom. Chem. 1992, 3, 239-244.
33. Schinazi, R. F.; Sommadossi, J.-P.; Saalmann, V.; Cannon, D.; Xie, M.-Y.; Hart, G.; Smith, G.; Hahn, E. Antimicrob. Agents Chemother. 1990, 34, 1061-1067.
34. Schinazi, R. F.; Fox, J. J.; Watanabe, K. A.; Nahmias, A. J. Antimicrob. Agents Chemother. 1986, 29, 77-84.
35. Chou, T.-C.; Talalay, P. Adv. Enzyme Regul. 1984, 22, 27-55.