Novel in vivo active anti-malarials based on a hydroxy-ethyl-amine scaffold

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 3, 2013, Pages 658-662

  Ciana, Claire Lise ^a   Siegrist, Romain ^a   Aissaoui, Hamed ^a   Marx, Léo ^a   Racine, Sophie ^a   Meyer, Solange ^a   Binkert, Christoph ^a   De Kanter, Ruben ^a   Fischli, Christoph ^b,c   Wittlin, Sergio ^b,c   Boss, Christoph ^a  

^a ACTELION PHARMACEUTICALS LTD   (Switzerland)

^b SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

^c UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Dual mechanism of action; Malaria; Mannich base; Medicinal chemistry; Speed of action

Indexed keywords

AMINE; AMODIAQUINE; ANTIMALARIAL AGENT; HYDROXY ETHYL AMINE; MANNICH BASE; UNCLASSIFIED DRUG;

ANTIMALARIAL ACTIVITY; ARTICLE; DRUG SCREENING; ERYTHROCYTE; INCUBATION TIME; MALARIA; MOLECULAR WEIGHT; NONHUMAN; PLASMODIUM FALCIPARUM;

ANIMALS; ANTIMALARIALS; ASPARTIC ACID ENDOPEPTIDASES; DISEASE MODELS, ANIMAL; ETHYLAMINES; HYDROXYLAMINE; INHIBITORY CONCENTRATION 50; MALARIA; MICE; MOLECULAR STRUCTURE; PLASMODIUM BERGHEI;

EID: 84872284777     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.11.118     Document Type: Article

References (22)

1. World Malaria Report 2011, WHO, 2011.
2. Global Report on Antimalarial Efficacy and Drug Resistance 2000-2010, WHO, 2010.
3. For examples see: K. Liu, H. Shi, H. Xiao, A.G.L. Chong, X. Bi, Y.-T. Chang, K.S.W. Tan, R.Y. Yada, and S.Q. Yao Angew. Chem., Int. Ed. 48 2009 8293
4. T.S. Haque, A.G. Skillman, C.E. Lee, H. Habashita, I.Y. Gluzman, T.J.A. Ewing, D.E. Goldberg, Irwin D. Kuntz, and J.A. Ellman J. Med. Chem. 2 1999 1428
5. D. Noeteberg, E. Hamelink, J. Hulten, M. Wahlgren, L. Vrang, B. Samuelsson, and A. Hallberg J. Med. Chem. 46 2003 734
6. C. Berry Curr. Opin. Drug Disc. Dev. 3 2000 624
7. C. Boss, S. Richard-Bildstein, T. Weller, W. Fischli, S. Meyer, and C. Binkert Curr. Med. Chem. 10 2003 883
8. J. Liu, Eva S. Istvan, I.Y. Gluzman, J. Gross, E. Daniel, and D.E. Goldberg Proc. Natl. Acad. Sci. U.S.A. 103 2006 8840
9. W. Trager, and J.B. Jensen Science 193 1976 673
10. F.-J. Gamo, L.M. Sanz, J. Vidal, C. de Cozar, E. Alvarez, J.-L. Lavandera, D.E. Vanderwall, D.V.S. Green, V. Kumar, S. Hasan, J.R. Brown, C.E. Peishoff, L.R. Cardon, and J.F. Garcia-Bustos Nature 465 2010 305
11. Y. Yuasa, Y. Yuasa, and H. Tsuruta Synth. Commun. 28 1998 395
12. S. Dei, E. Teodori, A. Garnier-Suillerot, F. Gualtieri, S. Scapecchi, R. Budriesi, and A. Chiarini Bioorg. Med. Chem. 9 2001 2673
13. Synthesized according to: D. Wang, and W.A. Nugent Org. Synth. 84 2007 58 or commercially available
14. R.E. Desjardins, C.J. Canfield, J.D. Haynes, and J.D. Chulay Antimicrob. Agents Chemother. 16 1979 710
15. C. Snyder, J. Chollet, J. Santo-Tomas, C. Scheurer, and S. Wittlin Exp. Parasitol. 115 2007 296
16. R.S. Obach, J.G. Baxter, T.E. Liston, B.M. Silber, B.C. Jones, F. MacIntyre, D.J. Rance, and P. Wastall J. Pharmacol. Exp. Ther. 283 1997 46
17. N.J. White Science 320 2008 330
18. For method see: R. Brunner, H. Aissaoui, C. Boss, Z. Bozdech, R. Brun, O. Corminboeuf, S. Delahaye, C. Fischli, B. Heidmann, M. Kaiser, J. Kamber, S. Meyer, P. Papastogiannidis, R. Siegrist, T. Voss, R. Welford, S. Wittlin, and C. Binkert J. Infect. Dis. 206 2012 735
19. B. Meunier Acc. Chem. Res. 41 2008 69
20. J. Chadwick, R.K. Amewu, F. Marti, F. Bousejra-El Garah, R. Sharma, N.G. Berry, P.A. Stocks, H. Burrell-Saward, S. Wittlin, M. Rottmann, R. Brun, D. Taramelli, S. Parapini, S.A. Ward, and P.M. O'Neill ChemMedChem 6 2011 1357
21. J.L. Maggs, N.R. Kitteringham, and B.K. Park Biochem. Pharmacol. 37 1988 303
22. A.C. Harrison, N.R. Kitteringham, J.B. Clarke, and B.K. Park Biochem. Pharmacol. 43 1992 1421