New developments in synthetic peroxidic drugs as artemisinin mimics

Drug Discovery Today

Volumn 12, Issue 11-12, 2007, Pages 487-495

  Jefford, Charles W ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIOXOLANE DERIVATIVE; ADENOSINE TRIPHOSPHATASE; ANTIMALARIAL AGENT; ANTIPARASITIC AGENT; ARTEKIN; ARTELINIC ACID; ARTEMETHER PLUS BENFLUMETOL; ARTEMISIN DERIVATIVE; ARTEMISININ; ARTESUNATE; ARTESUNATE PLUS CHLORPROGUANIL PLUS DAPSONE; ARTESUNATE PLUS PYRONARIDINE; CHLOROQUINE; CHLORPROGUANIL PLUS DAPSONE; DIHYDROARTEMISININ PLUS PIPERAQUINE; MEFLOQUINE; OZ 277; SESQUITERPENE DERIVATIVE; SESQUITERPENE TRIOXANE; SPIROCYCLOPENTYL TRIOXANE; SYNTHETIC PEROXIDE; TRIOXANE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIMALARIAL ACTIVITY; CHIRALITY; CLINICAL TRIAL; DRUG EFFICACY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; NONHUMAN; PARASITEMIA; PLASMODIUM; PLASMODIUM BERGHEI; PLASMODIUM YOELII; REVIEW;

ANIMALS; ANTIMALARIALS; ARTEMISININS; CYCLIZATION; DRUG DESIGN; HUMANS; MOLECULAR CONFORMATION; PEROXIDES; SESQUITERPENES;

EID: 34249012765     PISSN: 13596446     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.drudis.2007.04.009     Document Type: Review

References (54)

1. Meshnick S.R., et al. Second-generation antimalarial endoperoxides. Parasitol. Today 12 (1996) 79-82
2. Jefford C.W. Peroxidic antimalarials. Adv. Drug Res. 29 (1997) 271-325
3. Jefford C.W. Synthetic peroxides as antimalarials. Curr. Opin. Investig. Drugs 5 (2004) 866-872
4. Robert A., et al. From classical antimalarial drugs to new compounds based on the mechanism of action of artemisinin. Pure Appl. Chem. 73 (2001) 1173-1188
5. Robert A., et al. From mechanistic studies on artemisinin derivatives to new modular antimalarial drugs. Acc. Chem. Res. 35 (2002) 167-174
6. Ploypradith P. Development of artemisinin and its structurally simplified trioxane derivatives as antimalarial drugs. Acta Trop. 89 (2004) 329-342
7. Tang Y., et al. Synthetic peroxides as antimalarials. Med. Res. Rev. 24 (2004) 425-448
8. Posner G.H., et al. Antimalarial simplified 3-aryltrioxanes: synthesis and preclinical efficacy/toxicity testing in rodents. J. Med. Chem. 44 (2001) 3054-3058
9. Jefford C.W., et al. Synthesis, structure, and antimalarial activity of tricyclic 1,2,4-trioxanes related to artemisinin. Helv. Chim. Acta 76 (1993) 2775-2788
10. Posner G.H., and O'Neil P.M. Knowledge of the proposed chemical mechanism of action and cytochrome P450 metabolism of antimalarial trioxanes like artemisinin allows rational design of new antimalarial peroxides. Acc. Chem. Res. 37 (2004) 397-404
11. Jefford C.W. Why artemisinin and certain synthetic peroxides are potent antimalarials. Implications for the mode of action. Curr. Med. Chem. 8 (2001) 1803-1826
12. Jefford C.W., et al. The structure and antimalarial activity of some 1,2,4-trioxanes, 1,2,4,5-tetroxanes, and bicyclic endoperoxides. Implications for the mode of action. Heterocycles 52 (2000) 1345-1352
13. Dechy-Cabaret O., et al. Preparation and antimalarial activities of 'trioxaquines', new modular molecules with a trioxane skeleton linked to a 4-aminoquinoline. ChemBioChem 1 (2000) 281-283
14. Fitch C.D., et al. High-affinity accumulation of chloroquine by mouse erythrocytes infected with P. berghei. J. Clin. Investig. 54 (1974) 24-33
15. Chou A.C., et al. Ferriprotoporphyrin IX fulfills the criteria for identification as the chloroquine receptor of malaria parasites. Biochemistry 19 (1980) 1543-1549
16. Gu H.M., et al. Uptake of [H-3]-dihydroartemisinin by erythrocytes infected with Plasmodium falciparum in vitro. Trans. R. Soc. Trop. Med. Hyg. 78 (1984) 265-270
17. Dechy-Cabaret O., et al. Synthesis and antimalarial activity of trioxaquine derivatives. Chem. Eur. J. 10 (2004) 1625-1636
18. Singh C., et al. Synthesis and antimalarial activity of a new series of trioxaquines. Bioorg. Med. Chem. 12 (2004) 1177-1182
19. O'Neil P.M., and Posner G.H. A medicinal chemistry perspective on artemisinin and related endoperoxides. J. Med. Chem. 47 (2004) 2945-2964
20. Chen M., et al. Licochalcone A, a new antimalarial agent, inhibits in vitro growth of the human malaria parasite Plasmodium falciparum and protects mice from P. yoelii infection. Antimicrob. Agents Chemother. 38 (1994) 1470-1475
21. Li R., et al. In vitro antimalarial activity of chalcones and their derivatives. J. Med. Chem. 38 (1995) 5031-5037
22. O'Neil P.M., et al. Design and synthesis of endoperoxide prodrug models. Angew. Chem. Int. Ed. 43 (2004) 4193-4197
23. O'Neil P.M., et al. Application of thiol-olefin co-oxygenation methodology to a new synthesis of the 1,2,4-trioxane pharmacophore. Org. Lett. 6 (2004) 3035-3038
24. Singh C., et al. Photooxygenation of 3-aryl-2-cyclohexenols: synthesis of a new series of antimalarial 1,2,4-trioxanes. Tetrahedron Lett. 46 (2005) 205-207
25. Jefford C.W., et al. Cyclopenteno-1,2,4-trioxanes as effective antimalarial surrogates of artemisinin. In: Testa B., et al. (Ed). Perspectives in Medicinal Chemistry (1993), Verlag Helvetica Chimica Acta 459-472
26. Singh C., et al. Geraniol-derived 1,2,4-trioxanes with potent in vivo antimalarial activity. Bioorg. Med. Chem. Lett. 13 (2003) 3447-3450
27. Singh C., et al. Synthesis and antimalarial activity of 6-cycloalkylvinyl substituted 1,2,4-trioxanes. Bioorg. Med. Chem. 12 (2004) 5745-5752
28. Griesbeck A.G., et al. Novel spiroanellated 1,2,4-trioxanes with high in vitro antimalarial activities. Bioorg. Med. Chem. Lett. 15 (2005) 595-597
29. Kawanishi M., et al. Structure-activity relationship of antimalarial spongean peroxides having a 3-methoxy-1,2-dioxane structure. Bioorg. Med. Chem. 12 (2004) 5297-5307
30. Murakami N., et al. Synthesis of a bioprobe for elucidation of target molecule of spongean antimalarial peroxides. Bioorg. Med. Chem. Lett. 14 (2004) 3513-3516
31. Murakami N., et al. New readily accessible peroxides with high antimalarial activity. Bioorg. Med. Chem. Lett. 12 (2002) 69-72
32. Vennerstrom J.L., et al. Identification of an antimalarial synthetic trioxolane drug development candidate. Nature 430 (2004) 900-904
33. Tang Y., et al. Dispiro-1,2,4-trioxane analogues of a prototype dispiro-1,2,4-trioxolane: mechanistic comparators for artemisinin in the context of reaction pathways with iron(II). J. Org. Chem. 70 (2005) 5103-5110
34. Tang Y., et al. Synthesis of tetrasubstituted ozonides by the Griesbaum coozonolysis reaction: diastereoselectivity and functional group transformations by post-ozonolysis reactions. J. Org. Chem. 69 (2004) 6470-6473
35. O'Neil P.M. A worthy adversary for malaria. Nature 430 (2004) 838-839
36. Padmanilayam M., et al. Antimalarial activity of N-alkyl amine, carboxamide, sulfonamide, and urea derivatives of a disprio-1,2,4-trioxolane piperidine. Bioorg. Med. Chem. Lett. 16 (2006) 5542-5545
37. Dong Y., et al. Spiro and dispiro-1,2,4-trioxolanes as antimalarial peroxides: charting a workable structure activity relationship using simple prototypes. J. Med. Chem. 48 (2005) 4953-4961
38. Dong Y., et al. Effect of functional group polarity on the antimalarial activity of spiro and dispiro-1,2,4-trioxolanes. Bioorg. Med. Chem. 14 (2006) 6369-6382
39. Tang Y., et al. Weak base dispiro-1,2,4-trioxolanes: Potent antimalarial ozonides. Bioorg. Med. Chem. Lett. 17 (2007) 1260-1265
40. Robert A., and Meunier B. Is alkylation the main mechanism of action of the antimalarial drug artemisinin?. Chem. Soc. Rev. 27 (1998) 273-279
41. Wu W.M., et al. Unified mechanistic framework for the Fe(II)-induced cleavage of qinghaosu and derivatives/analogues. The first spin-trapping evidence for the previously postulated secondary C-4 radical. J. Am. Chem. Soc. 120 (1998) 3316-3325
42. Asawamahasakda W., et al. Effects of antimalarials and protease inhibitors on plasmodial hemozoin production. Mol. Biochem. Parasitol. 67 (1994) 183-191
43. Kannan R., et al. Reaction of artemisinin with haemoglobin: implications for antimalarial activity. Biochem. J. 385 (2005) 409-418
44. Jefford C.W. Synthesis, structure, and antimalarial activity of some enantiomerically pure, cis-fused cyclopenteno-1,2,4-trioxanes. Helv. Chim. Acta 78 (1995) 647-662
45. O'Neil P.M., et al. Enantiomeric 1,2,4-trioxanes display equivalent in vitro antimalarial activity versus Plasmodium falciparum malarial parasites: Implications for the molecular mechanism of action of the artemisinins. ChemBioChem 6 (2005) 2048-2054
46. Craig J.C., et al. Absolute configuration of the enantiomers of 7-chloro-4-[[4-(diethylamino)-1-methylbutyl]amino]quinoline (chloroquine). J. Org. Chem. 53 (1988) 1167-1170
47. Wernsdorfer W.H., et al. Activity of benflumetol and its enantiomers in fresh isolates of Plasmodium falciparum from East Africa. Acta Trop. 70 (1998) 9-15
48. Eckstein-Ludwig U., et al. Artemisinins target the SERCA of Plasmodium falciparum. Nature 424 (2003) 957-961
49. 2+ transport ATPase by thapsigargin at subnanomolar concentrations. J. Biol. Chem. 266 (1991) 13503-13506
50. Lytton J., et al. Thapsigargin inhibits the sarcoplasmic or endoplasmic reticulum Ca-ATPase family of calcium pumps. J. Biol. Chem. 266 (1991) 17067-17071
51. Uhlemann A.-C., et al. A single amino acid residue can determine the sensitivity of SERCAs to artemisinins. Nat. Struct. Mol. Biol. 12 (2005) 628-629
52. 2+-ATPase (PfATP6) and docking of artemisinin derivatives to PfATP6. Bioorg. Med. Chem. Lett. 15 (2005) 2994-2997
53. Biagini G.A., et al. Current drug development portfolio for antimalarial therapies. Curr. Opin. Pharmacol. 5 (2005) 473-478
54. Peters W., and Robinson B.L. The chemotherapy of rodent malaria. LVI. Studies on the development of resistance to natural and synthetic endoperoxides. Ann. Trop. Med. Parasitol. 93 (1999) 325-339