Collect. Czech. Chem. Commun.
2011, 76, 1187-1198
https://doi.org/10.1135/cccc2011105
Published online 2011-09-20 09:01:13
Efficient synthesis and biological properties of the 2′-trifluoromethyl analogues of acyclic nucleosides and acyclic nucleoside phosphonates
Petr Jansa*, Viktor Kolman, Alexandra Kostinová, Martin Dračínský, Helena Mertlíková-Kaiserová and Zlatko Janeba
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
References
1. E.: Nat. Rev. Drug Discovery 2002, 1, 13.
2. E., Holý A.: Nat. Rev. Drug Discovery 2005, 4, 928.
3. G.: Tetrahedron 1993, 49, 9385.
<https://doi.org/10.1016/S0040-4020(01)80212-X>
4. R., Pleven E., Heidelberger C.: J. Am. Chem. Soc. 1957, 79, 494.
<https://doi.org/10.1021/ja01573a087>
5. J. A.: Med. Res. Rev. 1982, 2, 271.
<https://doi.org/10.1002/med.2610020304>
6. G. K. S., Yudin A. K.: Chem. Rev. 1997, 97, 757.
<https://doi.org/10.1021/cr9408991>
7. D., Hocek M., Dvořáková H., Votruba I.: Tetrahedron 1999, 55, 11109.
<https://doi.org/10.1016/S0040-4020(99)00615-8>
8. E. A., Stephens O. M., Beal P. A.: Org. Lett. 2001, 3, 2969.
<https://doi.org/10.1021/ol016295i>
9. N.-S., Tang X.-Q., Piccirilli J. A.: Org. Lett. 2001, 3, 1025.
<https://doi.org/10.1021/ol0155687>
10. F., Gosselin G., Mathe C.: Org. Biomol. Chem. 2003, 1, 2096.
<https://doi.org/10.1039/b303093h>
11. F., Gosselin G., Standring D., Bryant M., Sommadossi J.-P., Loi A. G., La Colla P., Mathe C.: Bioorg. Med. Chem. 2002, 10, 3153.
<https://doi.org/10.1016/S0968-0896(02)00216-X>
12. J. P., Zhu F., Lemoff A., Kaiser M., Brun R., Guy R. K.: Bioorg. Med. Chem. 2010, 18, 8302.
<https://doi.org/10.1016/j.bmc.2010.09.073>
13. A., Schneller S. W.: Tetrahedron Lett. 2005, 46, 8913.
<https://doi.org/10.1016/j.tetlet.2005.10.064>
14. H., Holý A., Rosenberg I.: Collect. Czech. Chem. Commun. 1994, 59, 2069.
<https://doi.org/10.1135/cccc19942069>
15. K., Votruba I., Holý A., Pohl R.: Collect. Czech. Chem. Commun. 2006, 71, 595.
<https://doi.org/10.1135/cccc20060595>
16. Y., Zhukovskaya N., Zimmer M., Soelaiman S., Bergson P., Wang C., Gibbs C., Tang W.: Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 3242.
<https://doi.org/10.1073/pnas.0306552101>
17. D. G.: J. Med. Chem. 2010, 53, 4305.
<https://doi.org/10.1021/jm901024b>
18. Research Collaboratory for Structural Bioinformatics – Protein Data Bank (RCSB PDB); http://dx.doi.org/10.2210/pdb1pko/pdb.
19. Mark A. T.: ArgusLab 4.0.1. Planaria Software LLC, Seattle (WA) 2004; http://www.arguslab.com.
20. P., Holý A., Dračínský M., Baszczynski O., Česnek M., Janeba Z.: Green Chem. 2011, 13, 882.
<https://doi.org/10.1039/c0gc00509f>
21a. O., Jansa P., Dračínský M., Klepetářová B., Holý A., Votruba I., De Clercq E., Balzarini J., Janeba Z.: Bioorg. Med. Chem. 2011, 19, 2114.
<https://doi.org/10.1016/j.bmc.2011.02.050>
21b. Jansa P., Dračínský M., Holý A.: Collection Symposium Series (Hocek M., Ed.), Vol. 10, p. 360. Institute of Organic Chemistry, Academy of Sciences of the Czech Republic, Prague 2008.
21c. D., Masojídková M., Holý A.: Collect. Czech. Chem. Commun. 2005, 70, 247.
<https://doi.org/10.1135/cccc20050247>
21d. P., Dračínský M., Masojídková M., Šolínová V., Kašička V., Holý A.: Eur. J. Med. Chem. 2009, 44, 2408.
<https://doi.org/10.1016/j.ejmech.2008.09.031>
21e. M., Holý A., Pískala A., Masojídková M., Andrei G., Naesens L., Neyts J., Balzarini J., De Clercq E., Snoeck R.: J. Med. Chem. 2007, 50, 1069.
<https://doi.org/10.1021/jm061281+>
21f. M., Masojídková M., Holý A.: Bioorg. Med. Chem. 2010, 18, 387.
<https://doi.org/10.1016/j.bmc.2009.10.044>
22a. D., Pradere U., Roy V., Caillat C., Azzouzi A., Broggi J., Snoeck R., Andrei G., Lin J., Eriksson S., Alexandre J. A. C., El-Amri C., Deville-Bonne D., Meyer P., Balzarini J., Agrofoglio L. A.: J. Med. Chem. 2011, 54, 222.
<https://doi.org/10.1021/jm1011462>
22b. P., Špaček P., Votruba I., Břehová P., Dračínský M., Klepetářová B., Janeba Z.: Collect. Czech. Chem. Commun. 2011, 76, 1121.
<https://doi.org/10.1135/cccc2011074>

