Inhibitors of adenosine consuming parasites through polymer-assisted solution phase synthesis of lipophilic 5′-amido-5′-deoxyadenosine derivatives

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 4, 2009, Pages 1428-1436

  Heidler, Philipp ^a   Zohrabi Kalantari, Vida ^a   Kaiser, Marcel ^b   Brun, Reto ^b   Emmrich, Thomas ^c   Link, Andreas ^c  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

^c UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

Anti plasmodial activity; Modified nucleosides; Polymer bound reagents

Indexed keywords

5' AMINO 5' DEOXY N6 (4 PHENOXYBENZYL)ADENOSINE; ADENOSINE DERIVATIVE; INOSINE; UNCLASSIFIED DRUG;

ACYLATION; AMINOLYSIS; ARTICLE; DRUG SYNTHESIS; MALARIA; PLASMODIUM FALCIPARUM;

PLASMODIUM FALCIPARUM;

EID: 60049090429     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.01.026     Document Type: Article

References (34)

1. Gensini G.F., Conti A.A., and Lippi D. J. Infect. 54 (2007) 221
2. Schlitzer M. Arch. Pharm. 341 (2008) 149
3. Bathurst I., and Hentschel C. Trends Parasitol. 22 (2006) 301
4. Herforth C., Wiesner J., Franke S., Golisade A., Jomaa H., and Link A. J. Comb. Chem. 4 (2002) 302
5. Herforth C., Wiesner J., Heidler P., Sanderbrand S., Van Calenbergh S., Jomaa H., and Link A. Bioorg. Med. Chem. 12 (2004) 755
6. Zhao H., Pagano A.R., Wang W.M., Shallop A., Gaffney B.L., and Jones R.A. J. Org. Chem. 62 (1997) 7832
7. Mitsunobu O. Synthesis (1981) 1
8. Petricci E., Botta M., Corelli F., and Mugnaini C. Tetrahedron Lett. 43 (2002) 6507
9. Shao H., Zhang Q., Goodnow R., Chen L., and Tam S. Tetrahedron Lett. 41 (2000) 4257
10. Todd M.H., Oliver S.F., and Abell C. Org. Lett. 1 (1999) 1149
11. Todd M.H., Oliver S.F., and Abell C. Org. Lett. 1 (1999) 1687
12. Masala S., and Taddei M. Org. Lett. 1 (1999) 1355
13. Byun J.-W., Lee D.-H., and Lee Y.-S. Tetrahedron Lett. 44 (2003) 8063
14. Salvino J.M., Kumar N.V., Orton E., Airey J., Kiesow T., Crawford K., Mathew R., Krolikowski P., Drew M., Engers D., Krolikowski D., Herpin T., Gardyan M., McGeehan G., and Labaudiniere R. J. Comb. Chem. 2 (2000) 691
15. Caddick S., Hamza D., Wadman S.N., and Wilden J.D. Org. Lett. 4 (2002) 1775
16. Heidler P., and Link A. Bioorg. Med. Chem. 13 (2005) 585
17. Golisade A., Herforth C., Quirijnen L., Maes L., and Link A. Bioorg. Med. Chem. 10 (2002) 159
18. Yeh C.M., Tung C.L., and Sun C.M. J. Comb. Chem. 2 (2000) 341
19. Larsen T., and Link A. Angew. Chem., Int. Ed. 44 (2005) 4432
20. Isbell J. J. Comb. Chem. 10 (2008) 150
21. Kenner G.W., McDermott J.R., and Sheppard R.C. J. Chem. Soc., Chem. Commun. (1971) 636
22. Backes B.J., Virgilio A.A., and Ellman J.A. J. Am. Chem. Soc. 118 (1996) 3055
23. Thompson L.A., Moore F.L., Moon Y.-C., and Ellman J.A. J. Org. Chem. 63 (1998) 2066
24. Backes B.J., and Ellman J.A. J. Org. Chem. 64 (1999) 2322
25. Tang T.P., and Ellman J.A. J. Org. Chem. 67 (2002) 7819
26. Golisade A., Wiesner J., Herforth C., Jomaa H., and Link A. Bioorg. Med. Chem. 10 (2002) 769
27. Bressi J.C., Verlinde C., Aronov A.M., Le Shaw M., Shin S.S., Nguyen L.N., Suresh S., Buckner F.S., Van Voorhis W.C., Kuntz I.D., Hol W.G.J., and Gelb M.H. J. Med. Chem. 44 (2001) 2080
28. Jagtap P.G., Southan G.J., Baloglu E., Ram S., Mabley J.G., Marton A., Salzman A., and Szabo C. Bioorg. Med. Chem. Lett. 14 (2004) 81
29. Neres J., Labello N.P., Somu R.V., Boshoff H.I., Wilson D.J., Vannada J., Chen L., Barry III C.E., Bennett E.M., and Aldrich C.C. J. Med. Chem. 51 (2008) 5349
30. Cappellacci L., Franchetti P., Vita P., Petrelli R., Lavecchia A., Jayaram H.N., Saiko P., Graser G., Szekeres T., and Grifantini M. J. Med. Chem. 51 (2008) 4260
31. Dolezal K., Popa I., Hauserova E., Spichal L., Chakrabarty K., Novak O., Krystof V., Voller J., Holub J., and Strnad M. Bioorg. Med. Chem. 15 (2007) 3737
32. Bookser B.C., and Raffaele N.B. J. Org. Chem. 72 (2007) 173
33. Desjardins R.E., Canfield C.J., Haynes J.D., and Chulay J.D. Antimicrob. Agents Chemother. 16 (1979) 710
34. Matile H., and Pink J.R.L. In: Lefkovits I., and Pernis B. (Eds). Immunological Methods (1990), Academic Press, San Diego 221