Synthesis and biological evaluation of extraordinarily potent C-10 carba artemisinin dimers against P. falciparum malaria parasites and HL-60 cancer cells

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 3, 2009, Pages 1325-1338

  Chadwick, James ^a   Mercer, Amy E ^a   Park, B Kevin ^a   Cosstick, Richard ^a   O'Neill, Paul M ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

Artemisinin; Cancer; Dimer; Malaria

Indexed keywords

ARTEMISININ DERIVATIVE; CARBON; DIMER;

ANTIMALARIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NONHUMAN; PLASMODIUM FALCIPARUM; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ANIMALS; ANTIMALARIALS; ANTINEOPLASTIC AGENTS; ARTEMISININS; CELL LINE, TUMOR; DIMERIZATION; HL-60 CELLS; HUMANS; PLASMODIUM FALCIPARUM;

PLASMODIUM FALCIPARUM;

EID: 58949085353     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.12.017     Document Type: Article

References (27)

1. Liu J.-M., Ni M.-Y., Fan J.-F., Tu Y.-Y., Wu Z.-H., Wu Y.-L., and Chou W.-S. Acta Chim. Sin. 37 (1979) 129
2. Woerdenbag H.J., Moskal T.A., Pras N., Malingre T.M., Elferaly F.S., Kampinga H.H., and Konings A.W.T. J. Nat. Prod. 56 (1993) 849
3. Beekman A.C., Woerdenbag H.J., Kampinga H.H., and Konings A.W.T. Phytother. Res. 10 (1996) 140
4. Beekman A.C., Barentsen A.R.W., Woerdenbag H.J., VanUden W., Pras N., Konings A.W.T., ElFeraly F.S., Galal A.M., and Wikstrom H.V. J. Nat. Prod. 60 (1997) 325
5. Beekman A.C., Wierenga P.K., Woerdenbag H.J., Van Uden W., Pras N., Konings A.W.T., El-Feraly F.S., Galal A.M., and Wikstrom H.V. Planta Med. 64 (1998) 615
6. Efferth T. Drug Resist. Update 8 (2005) 85
7. Grace J.M., Aguilar A.J., Trotman K.M., and Brewer T.G. Drug Metab. Dispos. 26 (1998) 313
8. O'Neill P.M., Scheinmann F., Stachulski A.V., Maggs J.L., and Park B.K. J. Med. Chem. 44 (2001) 1467
9. O'Neill P.M., Searle N.L., Kan K.W., Storr R.C., Maggs J.L., Ward S.A., Raynes K., and Park B.K. J. Med. Chem. 42 (1999) 5487
10. O'Neill P.M., Pugh M., Stachulski A.V., Ward S.A., Davies J., and Park B.K. J. Chem. Soc., Perkin Trans. 1 (2001) 2682
11. Jeyadevan J.P., Bray P.G., Chadwick J., Mercer A.E., Byrne A., Ward S.A., Park B.K., Williams D.P., Cosstick R., Davies J., Higson A.P., Irving E., Posner G.H., and O'Neill P.M. J. Med. Chem. 47 (2004) 1290
12. Posner G.H., Ploypradith P., Hapangama W., Wang D.S., Cumming J.N., Dolan P., Kensler T.W., Klinedinst D., Shapiro T.A., Zheng Q.Y., Murray C.K., Pilkington L.G., Jayasinghe L.R., Bray J.F., and Daughenbaugh R. Bioorg. Med. Chem. 5 (1997) 1257
13. Posner G.H., Ploypradith P., Parker M.H., O'Dowd H., Woo S.H., Northrop J., Krasavin M., Dolan P., Kensler T.W., Xie S.J., and Shapiro T.A. J. Med. Chem. 42 (1999) 4275
14. Posner G.H., Paik I.H., Sur S., McRiner A.J., Borstnik K., Xie S.J., and Shapiro T.A. J. Med. Chem. 46 (2003) 1060
15. Posner G.H., McRiner A.J., Paik I.H., Sur S., Borstnik K., Xie S.J., Shapiro T.A., Alagbala A., and Foster B. J. Med. Chem. 47 (2004) 1299
16. Jung M., Lee S., Ham J., Lee K., Kim H., and Kim S.K. J. Med. Chem. 46 (2003) 987
17. Alagbala A.A., McRiner A.J., Borstnik K., Labonte T., Chang W., D'Angelo J.G., Posner G.H., and Foster B.A. J. Med. Chem. 49 (2006) 7836
18. Rodriguez M.J., Vasudevan V., Jamison J.A., Borromeo P.S., and Turner W.W. Bioorg. Med. Chem. 9 (1999) 1863
19. Hindley S., Ward S.A., Storr R.C., Searle N.L., Bray P.G., Park B.K., Davies J., and O'Neill P.M. J. Med. Chem. 45 (2002) 1052
20. Kobertz W.R., Bertozzi C.R., and Bednarski M.D. Tetrahedron Lett. 33 (1992) 737
21. Nakata T., Matsukura H., Jian D.L., and Nagashima H. Tetrahedron Lett. 35 (1994) 8229
22. Brown D.S., Bruno M., Davenport R.J., and Ley S.V. Tetrahedron 45 (1989) 4293
23. Posner G.H., Maxwell J.P., O'Dowd H., Krasavin M., Xie S.J., and Shapiro T.A. Bioorg. Med. Chem. 8 (2000) 1361
24. Still W.C., Kahn M., and Mitra A. J. Org. Chem. 43 (1978) 2923
25. Mosmann T. J. Immunol. Methods 65 (1983) 55
26. Jensen J.B., and Trager W. J. Parasitol. 63 (1977) 883
27. Desjardins R.E., Canfield C.J., Haynes D., and Chulay D.J. Antimicrob. Agents Chemother. 16 (1979) 710