P1,P2-Diimidazolyl derivatives of pyrophosphate and bis-phosphonates - Synthesis, properties, and use in preparation of dinucleoside tetraphosphates and analogs

Organic and Biomolecular Chemistry

Volumn 9, Issue 3, 2011, Pages 730-738

  Yanachkov, Ivan B ^a   Dix, Edward J ^a   Yanachkova, Milka I ^a   Wright, George E ^a  

^a GLSYNTHESIS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HIGH YIELD; PHOSPHONATES; TETRAPHOSPHATES;

DINUCLEOSIDE PHOSPHATE; IMIDAZOLE; IMIDAZOLE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PYROPHOSPHATE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

CYCLIZATION; DINUCLEOSIDE PHOSPHATES; DIPHOSPHATES; IMIDAZOLES; MOLECULAR STRUCTURE; PHOSPHONIC ACIDS;

EID: 79251522888     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob00542h     Document Type: Article

References (37)

1. Nucleoside triphosphates and their analogs: chemistry, biotechnology, and biological applications, ed., M. Vaghefi, Taylor & Francis: Boca Raton, 2005
2. K. Burgess D Cook Chem. Rev. 2000 100 6 2047 2060
3. 4A and Other Dinucleoside Polyphosphates, ed., A. G. McLennan, CRC Press: Boca Raton, 1992
4. C. H. V. Hoyle R. H. Hilderman J. J. Pintor H. Schlüter B. F. King Drug Dev. Res. 2001 52 260 273
5. A. G. McLennan Pharmacol. Ther. 2000 87 2-3 73 89
6. H. Schlüter E. Offers G. Brüggemann M. von der Giet M. Tepel E. Nordhoff M. Karas C. Spieker H. Witzel W. Zidek Nature 1994 367 186 188
7. Z. Palfi G. Suranyi G. Borbely Biochem. J. 1991 276 487 491
8. J. Eugen G. Verspohl M. H. N. Blackburn J. Hagemann M. Lempka J. Med. Chem. 2003 46 1554 1562
9. S. W. Chan S. J. Gallo B. K. Kim M. J. Guo G. M. Blackburn P. C. Zamecnik Proc. Natl. Acad. Sci. U. S. A. 1997 94 4034 4039
10. J. Pintor M. Diaz-Hernandez J. Gualix R. Gomez-Villafuertes F. Hernando M. T. Miras-Portugal Pharmacol. Ther. 2000 87 2-3 103 115
11. B. Walkowiak J. Baraniak C. S. Cierniewski W. Stec Bioorg. Med. Chem. Lett. 2002 12 15 1959 1962
12. W. Pendergast B. R. Yerxa J. G. Douglass 3rd S. R. Shaver R. W. Dougherty C. C. Redick I. F. Sims J. L. Rideout Bioorg. Med. Chem. Lett. 2001 11 2 157 160
13. E. A. Shirokova A. L. Khandazhinskaya Y. S. Skoblov L. Y. Goryunova R. S. Beabealashvilli A. A. Krayevsky Nucleosides, Nucleotides Nucleic Acids 2001 20 4 1033 1036
14. J. G. Douglass R. I. Patel B. R. Yerxa S. R. Shaver P. S. Watson K. Bednarski R. Plourde C. C. Redick K. Brubaker A. C. Jones J. L. Boyer J. Med. Chem. 2008 51 4 1007 1025
15. D. Kellerman A. R. Mospan J. Engels A. Schaberg J. Gorden L. Smiley Pulm. Pharmacol. Ther. 2008 21 4 600 607
16. J. Tauber W. F. Davitt M. D. Bokosky K. K. Nichols B. R. Yerxa A. E. Schaberg L. M. LaVange M. C. Mills-Wilson D. J. Kellerman Cornea 2004 23 8 784 792
17. Y. Kikuta E. Ohiwa K. Okada A. Watanabe S. Haruki Acta Anaesthesiol. Scand. 1999 43 1 82 86
18. D. L. M. Verheyden W. E. Wehrl J. G. Moffatt J. Org. Chem. 1965 30 3381 3385
19. 4A and Other Dinucleoside Polyphosphates, ed., A. G. McLennan, CRC Press: Boca Raton, 1992, pp. 305-342
20. N. B. Tarussova T. I. Osipova A. I. Biriukov M. J. Pokrovskaya C. V. Meshkov N. V. Gnuchev Nucl. Acids Res. Symp. Ser. 1984 14 287 288
21. G. M. Blackburn M. J. Guo Tetrahedron Lett. 1990 31 4371 4374
22. M. Maeda A. D. Patel A. Hampton Nucleic Acids Res. 1977 4 8 2843 2853
23. H. J. Ko R. L. Carter L. Cosyn R. Petrelli S. de Castro P. Besada Y. X. Zhou L. Cappellacci P. Franchetti M. Grifantini S. Van Calenbergh T. K. Harden K. A. Jacobson Bioorg. Med. Chem. 2008 16 12 6319 6332
24. Q. Han B. L. Gaffney R. A. Jones Org. Lett. 2006 8 2075 2077
25. N. B. Tarussova T. I. Osipova P. P. Purygin I. A. Yakimova Bioorg. Khim. 1986 12 404 407
26. N. B. Tarussova V. V. Shumiyanzeva A. C. Krylov M. Y. Karpeisky R. M. Khomutov Bioorg. Khim. 1983 9 838 843
27. J. C. Caesar D. V. Griffiths J. C. Tebby J. Chem. Soc., Perkin Trans. 1 1988 175 178
28. M. Kadokura T. Wada C. Urashima M. Sekine Tetrahedron Lett. 1997 38 48 8359 8362
29. C. E. McKenna L. A. Khawli W.-Y. Ahmad P. Pham J.-P. Bongartz Phosphorus Sulfur Relat. Elem. 1988 37 1
30. J. Vepsäläinen H. Nupponen E. Pohjala M. Ahlgren P. Vainiotalo J. Chem. Soc., Perkin Trans. 2 1992 835 842
31. Y. Xu L. Qian G. D. Prestwich Org. Lett. 2003 5 2267 2270
32. V. C. Nelson J. Labelled Compd. Radiopharm. 1996 38 713 723
33. This solution was prepared by neutralization of DMF solution of adenosine 5′-monophosphate, free acid, monohydrate with one equivalent of 55% (w/w) tetrabutylammonium hydroxide solution in water, and repeated evaporation under vacuum of the resulting solution from anhydrous DMF.
34. The coupling constants of this symmetrical spin system could not be measured directly from the NMR spectrum, and were determined by fitting of an AA′XX′ system to the experimental data (see ESI) using the WinDNMR program (Hans J. Reich, Department of Chemistry, University of Wisconsin).
35. F. Eckstein M. Goumet Nucleic Acid Chem. 1978 2 861 864
36. R. Dixon G. Lowe J. Biol. Chem. 1989 264 2069 2074
37. G. M. Blackburn G. E. Taylor G. R. J. Thatcher M. Prescott A. McLennan Nucleic Acids Res. 1987 15 6991 7004