Collect. Czech. Chem. Commun. 2011, 76, 1413-1431
https://doi.org/10.1135/cccc2011124
Published online 2011-11-30 18:56:19

7-Halogenated 7-deazapurine 2′-C-methylribonucleosides

Frank Seelaa,b,*, Simone Budowb, Kuiying Xub, Xioahua Pengb and Henning Eickmeierc

a Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Barbarastrasse 7, 49069 Osnabrück, Germany
b Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstrasse 11, 48149 Münster, Germany
c Anorganische Chemie II, Institut für Chemie, Universität Osnabrück, Barbarastrasse 7, 49069 Osnabrück, Germany

References

1. Furman P. A., Lam A. M., Murakami E.: Future Med. Chem. 2009, 1, 1429. <https://doi.org/10.4155/fmc.09.88>
2. De Francesco R., Migliaccio G.: Nature 2005, 436, 953. <https://doi.org/10.1038/nature04080>
3. De Clercq E., Holý A.: Nature Rev. 2005, 4, 928.
4. Eldrup A. B., Allerson C. R., Bennett C. F., Bera S., Bhat B., Bhat N., Bosserman M. R., Brooks J., Burlein C., Carroll S. S., Cook P. D., Getty K. L., MacCoss M., McMasters D. R., Olsen D. B., Prakash T. P., Prhavc M., Song Q., Tomassini J. E., Xia J.: J. Med. Chem. 2004, 47, 2283. <https://doi.org/10.1021/jm030424e>
5. Migliaccio G., Tomassini J. E., Carroll S. S., Tomei L., Altamura S., Bhat B., Bartholomew L., Bosserman M. R., Ceccacci A., Colwell L. F., Cortese R., De Francesco R., Eldrup A. B., Getty K. L., Hou X. S., LaFemina R. L., Ludmerer S. W., MacCoss M., McMasters D. R., Stahlhut M. W., Olsen D. B., Hazuda D. J., Flores O. A.: J. Biol. Chem. 2003, 278, 49164. <https://doi.org/10.1074/jbc.M305041200>
6. Eldrup A. B., Prhavc M., Brooks J., Bhat B., Prakash T. P., Song Q., Bera S., Bhat N., Dande P., Cook P. D., Bennett C. F., Carroll S. S., Ball R. G., Bosserman M., Burlein C., Colwell L. F., Fay J. F., Flores O. A., Getty K., LaFemina R. L., Leone J., MacCoss M., McMasters D. R., Tomassini J. E., Von Langen D., Wolanski B., Olsen D. B.: J. Med. Chem. 2004, 47, 5284. <https://doi.org/10.1021/jm040068f>
7. Olsen D. B., Eldrup A. B., Bartholomew L., Bhat B., Bosserman M. R., Ceccacci A., Colwell L. F., Fay J. F., Flores O. A., Getty K. L., Grobler J. A., LaFemina R. L., Markel E. J., Migliaccio G., Prhavc M., Stahlhut M. W., Tomassini J. E., MacCoss M., Hazuda D. J., Carroll S. S.: Antimicrob. Agents Chemother. 2004, 48, 3944. <https://doi.org/10.1128/AAC.48.10.3944-3953.2004>
8. Seela F., Peng X.: Curr. Top. Med. Chem. 2006, 6, 867. <https://doi.org/10.2174/156802606777303649>
9. Vorbrüggen H.: Acc. Chem. Res. 1995, 28, 509. <https://doi.org/10.1021/ar00060a007>
10. Harry-O'kuru R. E., Smith J. M., Wolfe M. S.: J. Org. Chem. 1997, 62, 1754. <https://doi.org/10.1021/jo961893+>
11. Ding Y., An H., Hong Z., Girardet J.-L.: Bioorg. Med. Chem. Lett. 2005, 15, 725. <https://doi.org/10.1016/j.bmcl.2004.11.019>
12. Bio M. M., Xu F., Waters M., Williams J. M., Savary K. A., Cowden C. J., Yang C., Buck E., Song Z. J., Tschaen D. M., Volante R. P., Reamer R. A., Grabowski E. J. J.: J. Org. Chem. 2004, 69, 6257. <https://doi.org/10.1021/jo0491096>
13. Seela F., Ming X.: Tetrahedron 2007, 63, 9850. <https://doi.org/10.1016/j.tet.2007.06.107>
14. Wang X., Seth P. P., Ranken R., Swayze E. E., Migawa M. T.: Nucleosides, Nucleotides Nucleic Acids 2004, 23, 161. <https://doi.org/10.1081/NCN-120027825>
15. Pudlo J. S., Saxena N. K., Nassiri M. R., Turk S. R., Drach J. C., Townsend L. B.: J. Med. Chem. 1988, 31, 2086. <https://doi.org/10.1021/jm00119a006>
16. Leroy F., Chaves D., Dukhan D., Storer R., Sommadossi J.-P., Loi A. G., Cadeddu A., Fanti M., Boscu N., Bassetti F., Liuzzi M., Gosselin G.: Nucleic Acids Symp. Ser. 2008, 52, 595. <https://doi.org/10.1093/nass/nrn301>
17. Seela F., Peng X.: Synthesis 2004, 1203. <https://doi.org/10.1055/s-2004-822382>
18. The only reference found in the literature for 11 is a patent (Cook P. D., Ewing G., Jin Y., Lambert J., Prhavc M., Rajappan V., Rajwanshi V. K., Sakthivel K.: PCT Patent 2005, WO 2005/021568 A2), where 11 was exemplified.
19. Nagahara K., Anderson J. D., Kini G. D., Dalley N. K., Larson S. B., Smee D. F., Jin A., Sharma B. S., Jolley W. B., Robins R. K., Cottam H. B.: J. Med. Chem. 1990, 33, 407. <https://doi.org/10.1021/jm00163a064>
20. Smee D. F., Alaghamandan H. A., Cottam H. B., Sharma B. S., Jolley W. B., Robins R. K.: Antimicrob. Agents Chemother. 1989, 33, 1487.
21. Smee D. F., Alaghamandan H. A., Jin A., Sharma B. S., Jolley W. B.: Antiviral Res. 1990, 13, 91. <https://doi.org/10.1016/0166-3542(90)90025-3>
22. The only reference found in the literature for 4 and 14 is a patent (Webber S. E., Haley G. J., Lennox J. R., Xiang A. X., Rueden E. J.: PCT Patent 2006, WO 2006/066080 A1), where both compounds were exemplified.
23a. Baker J. A., Chatfield P. V.: J. Chem. Soc. C 1969, 603. <https://doi.org/10.1039/j39690000603>
23b. Baker J. A., Chatfield P. V.: J. Chem. Soc. C 1970, 2478. <https://doi.org/10.1039/j39700002478>
24. Seela F., Ming X.: Org. Biomol. Chem. 2008, 6, 1450. <https://doi.org/10.1039/b718500f>
25. Seela F., Xu K., Chittepu P.: Synthesis 2006, 2005. <https://doi.org/10.1055/s-2006-942400>
26. Seela F., Peng X.: J. Org. Chem. 2006, 71, 81. <https://doi.org/10.1021/jo0516640>
27. Franchetti P., Cappellacci L., Marchetti S., Trincavelli L., Martini C., Mazzoni M. R., Lucacchini A., Grifantini M.: J. Med. Chem. 1998, 41, 1708. <https://doi.org/10.1021/jm9707737>
28. Murai Y., Shiroto H., Ishizaki T., Iimori T., Kodama Y., Ohtsuka Y., Oishi T.: Heterocycles 1992, 33, 391.
29. Beigelman L. N., Ermolinsky B. S., Gurskaya G. V., Tsapkina E. N., Karpeisky M. Y., Mikhailov S. N.: Carbohydr. Res. 1987, 166, 219. <https://doi.org/10.1016/0008-6215(87)80059-9>
30. Tsapkina E. N., Dzhavadova G. M., Gurskaya G. V., Beigelman L. N., Mikhailov S. N., Lindeman S. V.: Kristallografiya 1988, 33, 1415.
31. IUPAC-IUB Joint Commission on Biochemical Nomenclature: Eur. J. Biochem. 1983, 131, 9.
32. Seela F., Xu K., Eickmeier H.: Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2005, 61, o408. <https://doi.org/10.1107/S0108270105014265>
33. Flack H. D.: Acta Crystallogr., Sect. A: Fundam. Crystallogr. 1983, 39, 876. <https://doi.org/10.1107/S0108767383001762>