Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 7, 2009, Pages 2038-2043

  Araújo, Nuna C P ^a,b   Barton, Victoria ^b   Jones, Michael ^b   Stocks, Paul A ^b,c   Ward, Stephen A ^c   Davies, Jill ^c   Bray, Patrick G ^c   Shone, Alison E ^b,c   Cristiano, Maria L S ^a   O'Neill, Paul M ^b  

^a UNIVERSITY OF ALGARVE   (Portugal)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

^c LIVERPOOL SCHOOL OF TROPICAL MEDICINE   (United Kingdom)

Author keywords

Antimalarial; Drug hybrid; Plasmodium falciparum; Resistance

Indexed keywords

ARTEMETHER; ARTEMISININ; CHLOROQUINE; QUINOLINE DERIVATIVE;

ANTIMALARIAL ACTIVITY; ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PLASMODIUM FALCIPARUM; STRUCTURE ACTIVITY RELATION;

AMINACRINE; ANIMALS; ANTIMALARIALS; ARTEMISININS; PEROXIDES; PLASMODIUM FALCIPARUM; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP;

PLASMODIUM FALCIPARUM;

EID: 62149090637     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.02.013     Document Type: Article

References (40)

1. White N.J., Nosten F., Looareesuwan S., Watkins W.M., Marsh K., Snow R.W., Kokwaro G., Ouma J., Hien T.T., Molyneux M.E., Taylor T.E., Newbold C.I., Ruebush T.K., Danis M., Greenwood B.M., Anderson R.M., and Olliaro P. Lancet 353 (1999) 1965
2. Greenwood B.M., Fidock D.A., Kyle D.E., Kappe S.H.I., Alonso P.L., Collins F.H., and Duffy P.E. J. Clin. Invest. 118 (2008) 1266
3. Klayman D.L. Science 228 (1985) 1049
4. Krishna S., Woodrow C.J., Staines H.M., Haynes R.K., and Mercereau-Puijalon O. Trends Mol. Med. 12 (2006) 200
5. Haynes R.K., Fugmann B., Stetter J., Rieckmann K., Heilmann H.D., Chan H.W., Cheung M.K., Lam W.L., Wong H.N., Croft S.L., Vivas L., Rattray L., Stewart L., Peters W., Robinson B.L., Edstein M.D., Kotecka B., Kyle D.E., Beckermann B., Gerisch M., Radtke M., Schmuck G., Steinke W., Wollborn U., Schmeer K., and Romer A. Angew. Chem., Int. Ed. 44 (2005) 2064
6. Robert A., Benoit-Vical F., and Meunier B. Coord. Chem. Rev. 249 (2005) 1927
7. O'Neill P.M., and Posner G.H. J. Med. Chem. 47 (2004) 2945
8. Meshnick S.R., Thomas A., Ranz A., Xu C.M., and Pan H.P. Mol. Biochem. Parisitol. 49 (1991) 181
9. Meshnick S.R., Yang Y.Z., Lima V., Kuypers F., Kamchonwongpaisan S., and Yuthavong Y. Antimicrob. Agents Chemother. 37 (1993) 1108
10. White N. Philos. Trans. R. Soc. London, Ser. B-Biol. Sci. 354 (1999) 739
11. Tang Y.Q., Dong Y.X., and Vennerstrom J.L. Med. Res. Rev. 24 (2004) 425
12. Posner G.H., and O'Neill P.M. Acc. Chem. Res. 37 (2004) 397
13. Brewer T.G., Grate S.J., Peggins J.O., Weina P.J., Petras J.M., Levine B.S., Heiffer M.H., and Schuster B.G. Am. J. Trop. Med. Hyg. 51 (1994) 251
14. Bray P.G., Ward S.A., and O'Neill P.M. Malaria, Drugs, Disease and Post-Genomic Biology (Curr. Top. Microbiol. Immun.) (2005), Springer, Vol. 295 p 3
15. Vennerstrom J.L., Arbe-Barnes S., Brun R., Charman S.A., Chiu F.C.K., Chollet J., Dong Y.X., Dorn A., Hunziker D., Matile H., McIntosh K., Padmanilayam M., Tomas J.S., Scheurer C., Scorneaux B., Tang Y.Q., Urwyler H., Wittlin S., and Charman W.N. Nature 430 (2004) 900
16. Dong Y.X., Chollet J., Matile H., Charman S.A., Chiu F.C.K., Charman W.N., Scorneaux B., Urwyler H., Tomas J.S., Scheurer C., Snyder C., Dorn A., Wang X.F., Karle J.M., Tang Y.Q., Wittlin S., Brun R., and Vennerstrom J.L. J. Med. Chem. 48 (2005) 4953
17. http://www.mmv.org/. Currently drug development efforts are focused on OZ439, an analogue of OZ277, which has an improved metabolic stability and PK profile.
18. Dong Y.X., Tang Y.Q., Chollet J., Matile H., Wittlin S., Charman S.A., Charman W.N., Tomas J.S., Scheurer C., Snyder C., Scorneaux B., Bajpai S., Alexander S.A., Wang X.F., Padmanilayam M., Cheruku S.R., Brun R., and Vennerstrom J.L. Bioorg. Med. Chem. 14 (2006) 6368
19. Tang Y.Q., Dong Y.X., Wittlin S., Charman S.A., Chollet J., Chiu F.C.K., Charman W.N., Matile H., Urwyler H., Dorn A., Bajpai S., Wang X.F., Padmanilayam M., Karle J.M., Brun R., and Vennerstrom J.L. Bioorg. Med. Chem. 17 (2007) 1260
20. Dechy-Cabaret O., Benoit-Vical F., Robert A., and Meunier B. ChemBioChem 1 (2000) 281
21. Basco L.K., Dechy-Cabaret O., Ndounga M., Meche F.S., Robert A., and Meunier B. Antimicrob. Agents Chemother. 45 (2001) 1886
22. Robert A., Dechy-Cabaret O., Cazelles J., and Meunier B. Acc. Chem. Res. 35 (2002) 167
23. Meunier B. Acc. Chem. Res. 41 (2008) 69
24. Dechy-Cabaret O., Benoit-Vical F., Loup C., Robert A., Gornitzka H., Bonhoure A., Vial H., Magnaval J.F., Seguela J.P., and Meunier B. Chem. Eur. J. 10 (2004) 1625
25. Benoit-Vical F., Lelievre J., Berry A., Deymier C., Dechy-Cabaret O., Cazelles J., Loup C., Robert A., Magnaval J.F., and Meunier B. Antimicrob. Agents Chemother. 51 (2007) 1463
26. Singh C., Malik H., and Puri S.K. Bioorg. Med. Chem. 12 (2004) 1177
27. O'Neill P.M., Bishop L.P., Storr R.C., Hawley S.R., Maggs J.L., Ward S.A., and Park B.K. J. Med. Chem. 39 (1996) 4511
28. 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
29. Stocks P.A., Bray P.G., Barton V.E., Al-Helal M., Jones M., Araujo N.C., Gibbons P., Ward S.A., Hughes R.H., Biagini G.A., Davies J., Amewu R., Mercer A.E., Ellis G., and O'Neill P.M. Angew. Chem., Int. Ed. 46 (2007) 6278
30. 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
31. 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
32. 3 requires 530.2785.
33. 3 requires 544.2942.
34. 3) δ 156.8, 148.8, 148.0, 134.5, 131.7, 128.6, 126.0, 125.3, 125.1, 123.1, 111.5, 108.3, 100.5, 65.8, 62.3, 55.6, 52.6, 50.5, 36.4, 34.8, 34.8, 33.3, 26.9, 25.5, 15.2.
35. Trager W., and Jensien J.B. Nature 273 (1978) 621
36. Desjardins R.E., Canfield C.J., Haynes J.D., and Chulay J.D. Antimicrob. Agents Chemother. 16 (1979) 710
37. Warhurst D.C., Steele J.C.P., Adagu I.S., Craig J.C., and Cullander C. J. Antimicrob. Chemother. 52 (2003) 188
38. Eckstein-Ludwig U., Webb R.J., van Goethem I.D.A., East J.M., Lee A.G., Kimura M., O'Neill P.M., Bray P.G., Ward S.A., and Krishna S. Nature 424 (2003) 957
39. Tang Y.Q., Dong Y.X., Wang X.F., Sriraghavan K., Wood J.K., and Vennerstrom J.L. J. Org. Chem. 70 (2005) 5103
40. Coslédan F., Fraisse L., Pellet A., Guillou F., Mordmüller B., Kremsner P.G., Moreno A., Mazier D., Maffrand J.-P., and Meunier B. PNAS 105 (2008) 17579