Simple transformation of thymine 1-[3-hydroxy-2-(phosphonomethoxy)propyl] derivatives to their 1-[3-fluoro-2-(phosphonomethoxy)propyl] counterparts

Collection of Czechoslovak Chemical Communications

Volumn 70, Issue 9, 2005, Pages 1465-1481

  Pomeisl, Karel ^a   Pohl, Radek ^a   Holý, Antonín ^a   Votruba, Ivan ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Acyclic nucleoside phosphonates; Acyclic nucleotide analogues; Antivirals; Deoxyfluorinations; Pyrimidines; Thymidine phosphorylase; Thymine

Indexed keywords

EID: 28844469594     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20051465     Document Type: Article

References (30)

1. Holý A. in: Recent Advances in Nucleosides: Chemistry and Chemotherapy (C. K. Chu, Ed.), p. 167. Elsevier, Amsterdam 2002.
2. a) Jindřich J., Holý A., Dvořáková H.: Collect. Czech. Chem. Commun. 1993, 58, 1645;
3. b) Balzarini J., Holý A., Jindřich J., Dvořá ková H., Hao Z., Snoeck R.: Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 4961.
4. Holý A., Jindřich J., Balzarini J., De Clercq E.: Czech. Appl. 2047-90.
5. a) Harrada K., Matulie-Adamie J., Price R. W., Svhinazi R. F., Watanabe K. A., Fox J. J.: J. Med. Chem. 1987, 30, 226;
6. b) Hpwell H. G., Brodfuethrer P. R., Brundige S. P., Beningi D. A., Sapino C., Jr.: J. Org. Chem. 1988, 53, 85.
7. a) Singh R. P., Shreeve J. M.: Synthesis 2002, 17, 2561;
8. b) Haykawa H., Takai F., Tanaka H., Miyasaka T., Yamaguchi K.: Chem. Pharm. Bull. 1990, 38, 1136;
9. c) Middleton W. J.: J. Org. Chem. 1975, 40, 547;
10. d) Baasner B., Hagemann H., Tatlow J. C. (Eds): Methods of Organic Chemistry, Organo-Fluorine Compounds (Houben-Weyl), E10a. Thieme, Stuttgart, New York 1999.
11. Olah G. A., Welch J. T., Vanker Y. D., Nojima M., Kerekes I., Olah J. A.: J. Org. Chem. 1979, 44, 3872.
12. a) Yarovenko N. N., Raksha M. A.: Zh. Obshch. Khim. 1959, 29, 2159;
13. Chem. Abstr. 1960, 54, 9724;
14. b) Takaoka A., Iwakiri H., Ishikawa N.: Bull. Chem. Soc. Jpn. 1979, 52, 3377.
15. Novo B., Resnati G. in: Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets (V. A. Soloshonok, Ed.), p. 349. John Wiley, New York 1999.
16. Jindřich J., Holý A., Dvořáková H.: Collect. Czech. Chem. Commun. 1991, 57, 1466.
17. a) Balzarini J., Degréve B., Esteban-Gamboa A., Esnouf R., De Clercq E., Engelborghs Y., Camarasa M.-J., Pérez-Pérez M.-J.: FEBS Lett. 2000, 483, 181;
18. b) Esteban-Gamboa A., Balzarini J., Esnouf R., De Clercq E., Camarasa M.-J., Pérez-Pérez M.-J.: J. Med. Chem. 2000, 43, 971.
19. a) Beyl V., Niederprüm H., Voss P.: Justus Liegibs Ann. Chem. 1970, 731, 58;
20. b) Bennua-Skalmowski B., Vorbrüggen H.: Tetrahedron Lett. 1995, 36, 2611.
21. Holý A., Ivanova G. S.: Nucleic Acids Res. 1974, 1, 19.
22. a) Brodfuehrer P. R., Howell H. G., Sapino C., Jr., Vemishetti P.: Tetrahedron Lett. 1994, 35, 3243;
23. b) Holý A., Votruba I., Masojídková M.: Collect. Czech. Chem. Commun. 2001, 66, 1545.
24. Holý A.: Collect. Czech. Chem. Commun. 1993, 58, 649.
25. Holý A., Dvořáková H., Masojí dková M.: Collect. Czech. Chem. Commun. 1995, 60, 1390.
26. Takamatsu S., Katayama S., Hirose N., De Cock E., Schelkens G., Demilleguand M., Brepoel J., Izawa K.: Nucleosides Nucleotides Nucleic Acids 2002, 21, 849.
27. Parker D.: Chem. Rev. 1991, 91, 1441.
28. Votruba I., Pomeisl K., Tlouštová E., Holý A., Otová B.: Biochem. Pharmacol. 2005, 69, 1517.
29. Koga I., Funakoshi K., Matsuda A., Sakai K.: Tetrahedron: Asymmetry 1993, 4, 1857.
30. Holý A., Günter J., Dvořáková H., Masojídková M., Andrei G., Snoeck R., Balzarini J., De Clercq E.: J. Med. Chem. 1999, 42, 2064.