22
Views
12
CrossRef citations to date
0
Altmetric
Miscellaneous

Peroxidic antimalarials

Pages 1753-1760 | Published online: 25 Feb 2005

Bibliography

  • WORLD HEALTH ORGANISATION: The World Health Report 1997. World Health Organisation, Geneva (1997).
  • KLAYMAN DL: Qinghaosu (artemisinin): an antimalarial drug from China. Science (1985) 228:1049–1055.
  • POSNER GH: Antimalarial peroxides in the qinghaosu (artemisinin) and yingzhaosu families. Expert Opin. Ther. Patents (1998) 8:1487–1493.
  • ••An excellent review on peroxide-basedantimalarials through to mid-1998.
  • JEFFORD CW: Peroxidic antimalarials. In: Advances In Drug Research (Volume 29). Testa B, Meyer AU (Ed.), Academic Press, New York, USA (1997):271–325.
  • ••A superb early review of antimalarialperoxides.
  • CUMMING JN, PLOYPRADITH P, POSNER GH: Antimalarial activity of artemisinin (qinghaosu) and related trioxanes: mechanism(s) of action. Adv. Pharmacal. (1997) 37:253-297. A thorough mechanism of action review.
  • MESHNICK SR, TAYLOR TE, KAMCHONWONGPAISON S: Artemisinin and antimalarial endoperoxides: from herbal remedy to targeted chemotherapy. Microbial Rev (1996) 60: 301–315.
  • ••An elegant review from a biomedicalviewpoint.
  • WU WM, WU Y, WU YL 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. .Sc. (1998) 120:3316–3325.
  • ••The first report of a unified mechanismframework that can explain a large body of experimental observations.
  • WU Y, YUE ZY, WU YL: Interaction of qinghaosu (artemisinin) with cysteine sulfhydryl mediated by trace of non-heme iron. Angew. Chem. IriL Ed. (1999) 38:2580-2582. New insight into the parasiticidal action of artemisinin.
  • ROBERT A, CAZELLES J, MEUNIER B:Characterization of the alkylation product of heme by the antimalarial drug artemisinin. Angew. Chem. Int. Ed. (2001) 40:1954–1957.
  • •The first characterised haem-artemisinin covalent adducts in a chemical model.
  • POSNER GH, CUMMING JN, KRASAVIN M: Carbon-centred radicals and rational design of new antimalarial peroxide drugs. In: Biomedical Chemistry: Applying Chemical Priciples to the Understanding and Treatment of Disease. Torrence PF (Ed.), John Wiley & Sons, Inc., New York, USA (2000):289–309.
  • OLLIARO PL, HAYNES RK, MEUNIER B, YUTHAVONG Y: Possible modes of action of the artemisinin-type compounds. Trends Parasite]. (2001) 17:122–126.
  • •Summary of current ideas on the mechanism of action of artemisinins.
  • PETERS W, ROBINSON BL, ROSSITER JC, JEFFORD CW: The chemotherapy of rodent malaria. XLVIII. The activities of some synthetic 1,2,4-trioxanes against chloroquine-sensitive and chloroquine-resistant parasites. Part 1: studies leading to the development of novel cis-fused cyclopenteno derivatives. Ann. Trap. Med. Parasite]. (1993) 87:1–7.
  • BACHI MD, KORSHIN EE: Thiol-oxygen cooxidation of monoterpenes. Synthesis of endoperoxides structurally related to antimalarial yingzhaosu A. Syrilett (1998):122–125.
  • BACHI MD, KORSHIN EE, PLOYPRADITH P etal.: Synthesis and in vitro antimalarial activity of sulfone endoperoxides. Bioarg. Med. Chem. Lett. (1998) 8:903–908.
  • VENNERSTROM JL, FU HN, ELLIS WY etal.: Dispiro-1,2,4,5-tetraoxanes: a new class of antimalarial peroxides. j Med. Chem. (1992) 35:3023–3027.
  • DONG Y, MATILE H, CHOLLET J, KAMINSKY R, WOOD JK, VENNERSTROM JL: Synthesis and antimalarial activity of eleven dispro-12,4,5-tetraoxane analogues of WR 148999. 7,8, 15,16-Tetraoxadispiro [5.2.5.21-hexadecanes substituted at the 1 and 10 positions with unsaturated and polar functional groups. I Med. Chem. (1999) 42:1477–1480.
  • VENNERSTROM JL, DONG Y, ANDERSEN SL et al: Synthesis and antimalarial activity of sixteen dispiro-12,4,5-tetraoxanes: alkyl-substituted 7,8, 15,16-tetraoxadispiro [5.2.5.21-hexadecanes. j Med. Chem. (2000) 43:2753–2758.
  • TSUCHIYA K, HAMADA Y, MASUYAMA A et al: Synthesis, crystal structure and anti-malarial activity of novel spiro-1,2,4,5-tetraoxacycloalkanes. Tetrahedron Lett. (1999) 40:4077–4080.
  • NONAMI Y, TOKUYASU T, MASUYAMA A et al: Synthesis, crystal structure and antimalarial activity of functionalized spiro-1,2,4,5-tetraoxacycloalkanes from unsaturated hydroperoxy peracetals. Tetrahedron Lett. (2000) 41:4681–4684.
  • POSNER GH, CUMMING JN, WOO SH et al.: Orally active antimalarial 3-substitued trioxanes: new synthetic methodology and biological evaluation. I Med. Chem. (1998) 41:940–951.
  • VROMAN JA, ALVIM-GASTON, AVERY MA: Current progress in the chemistry, medicinal chemistry and drug design of artemisinin based antimalarials. Curr. Pharm. Des. (1999) 5:101–138.
  • O'NEIL PM, MILLER A, BICKLEY, JF, SCHEINMANN F, OH CH, POSNER GH: Asymmetric syntheses of enantiomeric 3-p-fluorophenyl 1,2,4-trioxane analogues of the antimalarial artemisinin. Tetrahedron Lett. (1999) 40:9133–9136.
  • POSNER GH, MAXWELL JP, O'DOWD H, KRASAVIN, M, XIE S, SHAPIRO TA: Antimalarial sulfide, sulfone, and sulfonamide trioxanes. Bioarg. Med. Chem. (2000) 8:1361–1370.
  • WHITE NJ: Antimalarial drug resistance and combination chemotherapy. Phil. Trans. R. Soc. Land. B (1999 ) 354:739–749.
  • VAN VM, WILAIRATANA P, GEMPERLI B et al: Efficacy of six doses of artemether-lumefantrine (benflumetol) in multidrug-resistant Plasmodium falciparum malaria. Am. J Trap. Med. Hyg. (1999) 60:936–942.
  • KARBWANG J, NA-BANGCHANG K, THANAVIBUL A, MULL R, GATHMAN I: Dose-finding study of the efficacy of fixed-combination artemether/lumefantrine for the treatment of multidrug-resistant Plasmodium falciparum malaria in Thailand. OM. Drug Invest. (2000) 19:343–348.
  • DECHY-CABARET 0, BENOIT-VICAL F, ROBERT A, MEUNIER B: Preparation and antimalarial activities of 'ffioxaquines', new modular molecules with a trioxane skeleton linked to a 4-aminoquinoline. Chem. Bio. Chem. (2000)1:281–283.
  • ••New exploration of combination therapywithin a single molecule.
  • BASCO LK, DECHY-CABARET 0, NDOUNGA M et al: In vitro activity of DU-1102, a new trioxaquine derivative, against PlasmodMm falciparum isolates. Antimicrob. Agents Chemother. (2001) 45:1886–1888.
  • VENNERSTROM JL: Amine peroxides as potential site-specific antimalarials. j Med. Chem. (1989) 32:64–67.
  • JEFFORD CW, KOHMOTO S, JAGGI D et al: Synthesis, structure, and antimalarial activity of some enantiomerically pure, CiS-fused cyclopenteno- 1, 2,4-trioxanes. Hely. Chim. Acta. (1995) 78:647–662.
  • JEFFORD CW, ROSSIER JC, MILHOUS WK: 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 (2000) 52:1345–1352.
  • O'NEILL PM, MILLER A, WARD SA, PARK BK, SCHEINMANN F, STACHULSKI AV: Application of the TMSOTf-AgC104 activator system to the synthesis of novel, potent, C-10 phenoxy derivatives of dihydroartemisinin. Tetrahedron Lett. (1999) 40:9129–9132.
  • O'NEILL PM, MILLER A, BISHOP LPD etal.: Synthesis, antimalarial activity, biomimetic iron(II) chemistry, and in vivo metabolism of novel, potent C-10-phenoxy derivatives of dihydroartemisinin. j Med. Chem. (2001) 44:58–68.
  • •Metabolism-based approach.
  • POSNER GH, PARKER MH, NORTHROP J et al.: Orally active, hydrolytically stable, semisyntheic, antimalarial trioxanes in the artemisinin family. j Med. Chem. (1999) 42:300–304.
  • •Short semisynthesis of orally active, enantiomerically pure, C-10 nonacetal carbon analogues of dihydroartemisinin.
  • O'DOWD H, PLOYPRADITH P, XIE S, SHAPIRO TA, POSNER GH: Antimalarial artemisinin analogues. Synthesis via chemoselective C-C bond formation and preliminary biological evaluation. Tetrahedron (1999) 55:3625–3636.
  • POSNER GH, PLOYPRADITH P, PARKER MH etal.: Antimalarial, antiproliferative, and antitumor activities of artemisinin-derived, chemically robust, trioxane dimers. j Med. Chem. (1999) 42:4275–4280.
  • AVERY MA, MEHROTRA S, JOHNSON TL, BONK JD, VROMAN JA, MILLER R: Structure-activity relationships of the antimalarial agent artemisinin. 5. Analogues of deoxoartemisinin substituted at C-3 and C-9. J. Med. Chem. (1996) 39:4149–4155.
  • TOROK DS, ZIFFER H: Synthesis and antimalarial activity of N-substituted 11-azaartemisinins. j Med. Chem. (1995) 38:5045–5050.
  • MEKONNEN B, ZIFFER H: A new route to Nsubstitued 11-azaartemisinins. Tetrahedron Lett. (1997) 38:731–734.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.