Artemisinin-quinoline hybrid-dimers: Synthesis and in vitro antiplasmodial activity

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 23, 2010, Pages 6975-6977

  Lombard, Marli C ^a   N'Da, David D ^a   Breytenbach, Jaco C ^a   Smith, Peter J ^b   Lategan, Carmen A ^b  

^a NORTH WEST UNIVERSITY   (South Africa)

^b UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

Dihydroartemisinin; Dimer; Hybrid; Malaria; Quinoline

Indexed keywords

AMINOQUINOLINE DERIVATIVE; CHLOROQUINE; DIHYDROARTEMISININ; DIHYDROARTEMISININ DERIVATIVE; DIMER; EMETINE;

ANTIPROTOZOAL ACTIVITY; ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PLASMODIUM FALCIPARUM;

ANIMALS; ANTIMALARIALS; ARTEMISININS; CHLOROQUINE; DIMERIZATION; DRUG RESISTANCE; PLASMODIUM FALCIPARUM; QUINOLINES;

PLASMODIUM FALCIPARUM;

EID: 78149409939     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.09.130     Document Type: Article

References (24)

1. J.P. Jeyadevan, P.G. Bray, J. Chadwick, A.E. Mercer, A. Byrne, S.A. Ward, B.K. Park, D.P. Williams, R. Cosstick, J. Davies, A.P. Higson, E. Irving, G.H. Posner, and P.M. O'Neill J. Med. Chem. 47 2004 1290
2. A.M. Galal, W. Gul, D. Slade, S.A. Ross, S. Feng, M.G. Hollingshead, M.C. Alley, G. Kaur, and M.A. ElSohly Bioorg. Med. Chem. 17 2009 741
3. J. Chadwick, A.E. Mercer, B.K. Park, R. Cosstick, and P.M. O'Neill Bioorg. Med. Chem. 17 2009 1325
4. A.S. Rosenthal, X. Chen, J.O. Liu, D.C. West, P.J. Hergenrother, T.A. Shapiro, and G.H. Posner J. Med. Chem. 52 2009 1198
5. G.H. Posner, J. Northrop, I. Paik, K. Borstnik, P. Dolan, T.W. Kensler, S. Xie, and T.A. Shapiro Bioorg. Med. Chem. 10 2002 227
6. D. Slade, A.M. Galal, W. Gul, M.M. Radwan, S.A. Ahmed, S.I. Khan, B.L. Tekwani, M.R. Jacob, S.A. Ross, and M.A. ElSohly Bioorg. Med. Chem. 17 2009 7949
7. K. Kaur, M. Jain, R.P. Reddy, and R.l. Jain Eur. J. Med. Chem. 45 2010 3245
8. N.C.P. Araújo, V. Barton, M. Jones, P.A. Stocks, S.A. Ward, J. Davies, P.G. Bray, A.E. Shone, M.L.S. Cristiano, and P.M. O'Neill Bioorg. Med. Chem. Lett. 19 2009 2038
9. F. Bellot, F. Cosledan, L. Vendier, J. Brocard, B. Meunier, and A. Robert J. Med. Chem. 53 2010 4103
10. O. Dechy-Cabaret, F. Benoit-Vical, C. Loup, A. Robert, H. Gornitzka, A. Bonhoure, H. Vial, J. Magnaval, J. Séguéla, and B. Meunier Chem. Eur. J. 10 2004 1625
11. B. Meunier Acc. Chem. Res. 41 2008 69
12. M.C. Lombard, M.A. Fernandes, J.C. Breytenbach, and D.D. N'Da Acta Crystallogr., Sect. E E66 2010 2182
13. Y. Li, Y. Zhu, H. Jiang, J. Pan, G. Wu, J. Wu, Y. Shi, J. Yang, and B. Wu J. Med. Chem. 43 2000 1635
14. 3) 7.18 (s, 1H, H-8′′′), 5.28 (s, 2H, H-12; H-12′), 4.71 (d, J = 3.4 Hz, 2H, H-10; H-10′), 3.94 (dt, J = 10.9, 5.6 Hz, 2H, H-1α′′′; H-4α′′′), 3.56-3.50 (m, 2H, H-H-1β′′′; H-4β′′′), 3.35 (dd, J = 10.2, 5.7 Hz, 2H, H-7′′′), 2.84-2.79 (m, 4H, H-2′′′; H-3′′′), 2.77 (dd, J = 11.6, 5.8 Hz, 1H, H-5α′′′), 2.74-2.69 (m, 1H, H- 5β′′′), 1.91-1.85 (m, 2H, H-6′′′), 1.36 (s, 6H, 3-Me; 3′-Me), 0.84-0.80 (m, 12H, 9-Me; 9′-Me; 6-Me; 6′-Me).
15. M. Calas, M. Ouattara, G. Piquet, Z. Ziora, Y. Bordat, M.L. Ancelin, R. Escale, and H. Vial J. Med. Chem. 50 2007 6307
16. T. Thorsteinsson, M. Masson, K.G. Kristinsson, M.A. Hjalmarsdottir, H. Hilmarsson, and T. Loftsson J. Med. Chem. 46 2003 4173
17. C. Biot, W. Daher, C.M. Ndiaye, P. Melnyk, B. Pradines, N. Chavain, A. Pellet, L. Fraisse, L. Pelinski, C. Jarry, J. Brocard, J. Khalife, I. Forfar-Bares, and D. Dive J. Med. Chem. 49 2006 4707
18. N. Sundu, M. Sharma, K. Srivastava, S. Rajakumar, S.K. Puri, J.K. Saxena, and P.M.S. Chauhan Bioorg. Med. Chem. 17 2009 6451
19. K. Yearick, K. Ekoue-Kovi, D. Iwaniuk, J.K. Natarajan, J. Alumasa, A.C. de Dios, P.D. Roepe, and C. Wolf J. Med. Chem. 51 2008 1995
20. P. Pillay, R. Vleggaar, V.J. Maharaj, P.J. Smith, and C.A. Lategan J. Ethnopharmacol. 112 2007 71
21. M.T. Makler, J.M. Ries, J.A. Williams, J.E. Bancroft, R.C. Peper, B.L. Gibbins, and D.J. Hinrichs Am. Soc. Trop. Med. Hyg. 48 1993 739
22. W. Trager, and J.B. Jensen Science 193 1976 673
23. T. Mosmann J. Immunol. Methods 65 1983 55
24. L.V. Rubinstein, R.H. Shoemaker, K.D. Paull, R.M. Simon, S. Tosini, P. Skehan, D.A. Scrudiero, A. Monks, and M.R. Boyd J. Natl. Cancer Inst. 82 1990 1113