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Volumn 41, Issue 6, 1998, Pages 940-951

Orally active antimalarial 3-substituted trioxanes: New synthetic methodology and biological evaluation

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIOXANE DERIVATIVE; ANTIMALARIAL AGENT; IRON DERIVATIVE;

EID: 0032510451     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970686e     Document Type: Article
Times cited : (81)

References (35)
  • 2
    • 0030013590 scopus 로고    scopus 로고
    • Artemether in Severe Malaria-Still Too many Deaths
    • Hoffmann, S. L. Artemether in Severe Malaria-Still Too Many Deaths. N. Engl. J. Med. 1996, 335, 124-126.
    • (1996) N. Engl. J. Med. , vol.335 , pp. 124-126
    • Hoffmann, S.L.1
  • 4
    • 0027509620 scopus 로고
    • Qinghaosu
    • Hien, T. T.; White, N. J. Qinghaosu. Lancet 1993, 341, 603-608.
    • (1993) Lancet , vol.341 , pp. 603-608
    • Hien, T.T.1    White, N.J.2
  • 5
    • 0021948029 scopus 로고
    • Qinghaosu (Artemisinin): An Antimalarial Drug from China
    • Klayman, D. L. Qinghaosu (Artemisinin): an Antimalarial Drug from China. Science 1985, 228, 1049-1055.
    • (1985) Science , vol.228 , pp. 1049-1055
    • Klayman, D.L.1
  • 6
    • 0001985625 scopus 로고
    • Total Synthesis of the Antimalarial Sesquiterpene Peroxide Qinghaosu and Yingzhaosu a
    • Zhou, W. S.; Xu, X. X. Total Synthesis of the Antimalarial Sesquiterpene Peroxide Qinghaosu and Yingzhaosu A. Ace. Chem. Res. 1994, 27, 211-216.
    • (1994) Ace. Chem. Res. , vol.27 , pp. 211-216
    • Zhou, W.S.1    Xu, X.X.2
  • 7
    • 0003095812 scopus 로고
    • Current Developments in the Chemistry of Artemisinin and
    • Jung, M. Current Developments in the Chemistry of Artemisinin and Related Compounds. Curr. Med. Chem. 1994, 1, 46-60.
    • (1994) Curr. Med. Chem. , vol.1 , pp. 46-60
    • Jung, M.1    Compounds, R.2
  • 8
    • 1842334506 scopus 로고    scopus 로고
    • The Pharmacokinetics of a Single Dose of Artemisinin in Patients with Uncomplicated Falciparum Malaria
    • For a recent pharmacokinetic study of artemisinin used to treat patients with malaria, see: De Vries, P. J.; Dien, T. K.; Khanh, N. X.; Binh, L. N.; Yen, P. T.; Duc, D. D.; C. J., V. B.; Kager, P. A. The Pharmacokinetics of a Single Dose of Artemisinin in Patients with Uncomplicated Falciparum Malaria. Am. J. Trop. Med. Hyg. 1997, 56, 503-507.
    • (1997) Am. J. Trop. Med. Hyg. , vol.56 , pp. 503-507
    • De Vries, P.J.1    Dien, T.K.2    Khanh, N.X.3    Binh, L.N.4    Yen, P.T.5    Duc, D.D.6    Kager, P.A.7
  • 9
    • 0029886413 scopus 로고    scopus 로고
    • Structure-Activity Relationships of the Antimalarial Agent Artemisinin. 3. Total Synthesis of (+)-13-Carbaartemisinin and Related Tetra- And Tricyclic Structures
    • For a leading reference, see: Avery, M. A.; Fan, P.; Karle, J. M.; Bonk, J. D.; Miller, R.; Coins, D. K. Structure-Activity Relationships of the Antimalarial Agent Artemisinin. 3. Total Synthesis of (+)-13-Carbaartemisinin and Related Tetra- and Tricyclic Structures. J. Med. Chem. 1996, 39, 1885-1897.
    • (1996) J. Med. Chem. , vol.39 , pp. 1885-1897
    • Avery, M.A.1    Fan, P.2    Karle, J.M.3    Bonk, J.D.4    Miller, R.5    Coins, D.K.6
  • 10
    • 0029894037 scopus 로고    scopus 로고
    • Artemisinin and the Antimalarial Endoperoxides: From Herbal Remedy to Targeted Chemotherapy
    • Meshnick, S. R.; Taylor, T. E.; Kamchonwongpaisan, S. Artemisinin and the Antimalarial Endoperoxides: from Herbal Remedy to Targeted Chemotherapy. Microbiol Rev. 1996, 60, 301-315.
    • (1996) Microbiol Rev. , vol.60 , pp. 301-315
    • Meshnick, S.R.1    Taylor, T.E.2    Kamchonwongpaisan, S.3
  • 12
    • 0026014249 scopus 로고
    • Artemisinin (Qinghaosu): The Role of Intracellular Hemin in its Mechanism of Antimalarial Action. Mol
    • For the first report on the importance of iron in triggering the cytotoxic effects of trioxanes, see: Meshnick, S. R.; Thomas, A.; Ranz, A.; Xu, C. M.; Pan, H. P. Artemisinin (Qinghaosu): the Role of Intracellular Hemin in its Mechanism of Antimalarial Action. Mol. Biochem. Parasitol. 1991, 49, 181-190.
    • (1991) Biochem. Parasitol. , vol.49 , pp. 181-190
    • Meshnick, S.R.1    Thomas, A.2    Ranz, A.3    Xu, C.M.4    Pan, H.P.5
  • 13
    • 0029038225 scopus 로고
    • Evidence for Fe(IV)=O in the Molecular Mechanism of Action of the Trioxane Antimalarial Artemisinin
    • Posner, G. H.; Gumming, J. N.; Ploypradith, P.; Oh, C. H. Evidence for Fe(IV)=O in the Molecular Mechanism of Action of the Trioxane Antimalarial Artemisinin. J. Am. Chem. Soc. 1995, 117, 5885-5886.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5885-5886
    • Posner, G.H.1    Gumming, J.N.2    Ploypradith, P.3    Oh, C.H.4
  • 14
    • 0023905646 scopus 로고
    • Toxic DNA Damage by Hydrogen : Peroxide through the Fenton Reaction in Vivo and in Vitro
    • Imlay, J. A.; S. M., C.; Linn, S. Toxic DNA Damage by Hydrogen : Peroxide Through the Fenton Reaction in Vivo and in Vitro. Science 1988, 240, 640-642.
    • (1988) Science , vol.240 , pp. 640-642
  • 15
    • 0001428908 scopus 로고    scopus 로고
    • Characterization of the First Covalent Adduct between Artemisinin and a Heme Model
    • Robert, A.; Meunier, B. Characterization of the First Covalent Adduct between Artemisinin and a Heme Model. J. Am. Chem. Soc. 1997, 779, 5968-5969.
    • (1997) J. Am. Chem. Soc. , vol.779 , pp. 5968-5969
    • Robert, A.1    Meunier, B.2
  • 16
    • 0027770863 scopus 로고
    • 198. Synthesis, Structure, and Antimalarial Activity of Tricyclic 1,2,4-Trioxanes Related to Artemisinin
    • Jefford, C. W.; Velarde, J. A.; Bernardinelli, G.; Bray, D. H.; Warhurst, D. G.; Milhous, W. K. 198. Synthesis, Structure, and Antimalarial Activity of Tricyclic 1,2,4-Trioxanes Related to Artemisinin. Helv. Chim. Acta 1993, 76, 2775-2788.
    • (1993) Helv. Chim. Acta , vol.76 , pp. 2775-2788
    • Jefford, C.W.1    Velarde, J.A.2    Bernardinelli, G.3    Bray, D.H.4    Warhurst, D.G.5    Milhous, W.K.6
  • 17
    • 0004060828 scopus 로고
    • Hudlicky, M., Pavlath, A. E., Eds.; American Chemical Society Monograph 187; American Chemical Society: Washington, DC
    • Chemistry of Organic Fluorine Compounds. IL A Critical Review; Hudlicky, M., Pavlath, A. E., Eds.; American Chemical Society Monograph 187; American Chemical Society: Washington, DC, 1995.
    • (1995) Chemistry of Organic Fluorine Compounds. IL a Critical Review
  • 18
    • 0030003137 scopus 로고    scopus 로고
    • Structure-Activity Relationships of the Antimalarial Agent Artemisinin. 4. Effect of Substitution at C-3
    • Avery, M. A.; Mehrotra, S.; Bonk, J. D.; Vroman, J. A.; Coins, D. K.; Miller, R. Structure-Activity Relationships of the Antimalarial Agent Artemisinin. 4. Effect of Substitution at C-3. J. Med. Chem. 1996, 39, 2900-2906.
    • (1996) J. Med. Chem. , vol.39 , pp. 2900-2906
    • Avery, M.A.1    Mehrotra, S.2    Bonk, J.D.3    Vroman, J.A.4    Coins, D.K.5    Miller, R.6
  • 19
    • 0029995163 scopus 로고    scopus 로고
    • Evidence for the Importance of High-Valent Fe=O and of a Diketone in the Molecular Mechanism of Action of Antimalarial Trioxane Analogues of Artemisinin
    • Posner, G. H.; Park, S. B.; Gonzalez, L.; Wang, D.; Gumming, J. N.; Klinedinst, D.; Shapiro, T. A.; Bachi, M. D. Evidence for the Importance of High-Valent Fe=O and of a Diketone in the Molecular Mechanism of Action of Antimalarial Trioxane Analogues of Artemisinin. J. Am. Chem. Soc. 1996,118,3537-3538.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 3537-3538
    • Posner, G.H.1    Park, S.B.2    Gonzalez, L.3    Wang, D.4    Gumming, J.N.5    Klinedinst, D.6    Shapiro, T.A.7    Bachi, M.D.8
  • 20
    • 0028788118 scopus 로고
    • Synthesis and Antimalarial Activities of Several Fluorinated Artemisinin Derivatives
    • Pu, Y. M.; Torok, D. S.; Ziffer, H. Synthesis and Antimalarial Activities of Several Fluorinated Artemisinin Derivatives. J. Med. Chem. 1995, 38, 4120-4124.
    • (1995) J. Med. Chem. , vol.38 , pp. 4120-4124
    • Pu, Y.M.1    Torok, D.S.2    Ziffer, H.3
  • 21
    • 0000576004 scopus 로고    scopus 로고
    • Antimalarial 1,2,4-Trioxanes Related to Artemisinin: Rules for Assignment of Relative Stereochemistry in Diversely Substituted Analogues
    • Oh, G. H.; Wang, D.; Cumming, J. N.; Posner, G. H. Antimalarial 1,2,4-Trioxanes Related to Artemisinin: Rules for Assignment of Relative Stereochemistry in Diversely Substituted Analogues. Spectrosc. Lett. 1997, 30, 241-255.
    • (1997) Spectrosc. Lett. , vol.30 , pp. 241-255
    • Oh, G.H.1    Wang, D.2    Cumming, J.N.3    Posner, G.H.4
  • 22
    • 12444296964 scopus 로고    scopus 로고
    • Synthesis and Antimalarial Activity of Heteroatom-Containing Bicyclic Endoperoxides
    • Posner, G. H.; Gonzalez, L.; Cumming, J. N.; Klinedinst, D.; Shapiro, T. A. Synthesis and Antimalarial Activity of Heteroatom-Containing Bicyclic Endoperoxides. Tetrahedron 1997, 53, 37-50.
    • (1997) Tetrahedron , vol.53 , pp. 37-50
    • Posner, G.H.1    Gonzalez, L.2    Cumming, J.N.3    Klinedinst, D.4    Shapiro, T.A.5
  • 23
    • 0019395570 scopus 로고
    • Chloroquine Sensitivity of Isolates of Plasmodium falciparum Adapted to in Vitro Culture.Trop
    • Ponnudurai, T.; Leeuwenberg, A. D. E. M.; Meuwissen, J. H. E. T. Chloroquine Sensitivity of Isolates of Plasmodium falciparum Adapted to In Vitro Culture.Trop. Geogr. Med. 1981, 33, 5054.
    • (1981) Geogr. Med. , vol.33 , pp. 5054
    • Ponnudurai, T.1    Leeuwenberg, A.D.E.M.2    Meuwissen, J.H.E.T.3
  • 24
    • 33847482116 scopus 로고    scopus 로고
    • We thank Dr. Alexandra Fairfield, NIH Division of AIDS, Therapeutic Research Program, for arranging these studies in L929 cells
    • We thank Dr. Alexandra Fairfield, NIH Division of AIDS, Therapeutic Research Program, for arranging these studies in L929 cells.
  • 25
    • 0028293959 scopus 로고
    • New, Antimalarial, Tricyclic 1,2,4-Trioxanes: Preclinical Evaluation in Mice and Monkeys
    • Posner, G. H.; Oh, C. H.; Webster, K.; Ager, A. L., Jr.; Rossan, R. N. New, Antimalarial, Tricyclic 1,2,4-Trioxanes: Preclinical Evaluation in Mice and Monkeys. Am. J. Trop. Med. Hyg. 1994, 50, 522-526.
    • (1994) Am. J. Trop. Med. Hyg. , vol.50 , pp. 522-526
    • Posner, G.H.1    Oh, C.H.2    Webster, K.3    Ager Jr., A.L.4    Rossan, R.N.5
  • 26
    • 0027157991 scopus 로고
    • 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
    • Peters, W.; Robinson, B. L.; Rossiter, J. C.; Jeflbrd, C. W. 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. Trop. Med. Parasitai. 1993, 87, 1-7.
    • (1993) Ann. Trop. Med. Parasitai. , vol.87 , pp. 1-7
    • Peters, W.1    Robinson, B.L.2    Rossiter, J.C.3    Jeflbrd, C.W.4
  • 27
    • 0029013609 scopus 로고
    • Further Evidence Supporting the Importance of and Restrictions on a Carbon-Centered Radical for High Antimalarial Activity of 1,2,4-Trioxanes like Artemisinin
    • Posner, G. H.; Wang, D.; Gumming, J. N.; Oh, C. H.; French, A. N.; Bodley, A. L.; Shapiro, T. A. Further Evidence Supporting the Importance of and Restrictions on a Carbon-Centered Radical for High Antimalarial Activity of 1,2,4-Trioxanes Like Artemisinin. J. Med. Chem. 1995, 38, 2273-2275.
    • (1995) J. Med. Chem. , vol.38 , pp. 2273-2275
    • Posner, G.H.1    Wang, D.2    Gumming, J.N.3    Oh, C.H.4    French, A.N.5    Bodley, A.L.6    Shapiro, T.A.7
  • 28
    • 33847475987 scopus 로고    scopus 로고
    • The two major degradation products were the corresponding previously seen11'13 ring-contracted tetrahydrofurans (35-40% yields) and the corresponding deoxy (i.e. peroxide-reduced) lactols (25-30% yields).
    • The two major degradation products were the corresponding previously seen11'13 ring-contracted tetrahydrofurans (35-40% yields) and the corresponding deoxy (i.e. peroxide-reduced) lactols (25-30% yields).
  • 29
    • 84987550737 scopus 로고
    • Synthesis and Antimalarial Activities of Structurally Simplified 1,2,4Trioxanes Related to Artemisinin
    • Posner, G. H.; Oh, C. H.; Gerena, L.; Milhous, W. K. Synthesis and Antimalarial Activities of Structurally Simplified 1,2,4Trioxanes Related to Artemisinin. Heteroatom Chem. 1993, 6, 105-116.
    • (1993) Heteroatom Chem. , vol.6 , pp. 105-116
    • Posner, G.H.1    Oh, C.H.2    Gerena, L.3    Milhous, W.K.4
  • 31
    • 0029159686 scopus 로고
    • Photoinduced Energy Transfer in Associated by Noncovalently Linked Photosynthetic Model Systems
    • Sessler, J. L.; Wang, B.; Harriman, A. Photoinduced Energy Transfer in Associated by Noncovalently Linked Photosynthetic Model Systems. J. Am. Chem. Soc. 1995, 117, 704-714.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 704-714
    • Sessler, J.L.1    Wang, B.2    Harriman, A.3
  • 32
    • 0027979875 scopus 로고
    • Synthesis of a Fluorescent Steroid Derivative with High Affinities for the Glucocorticoid and Progesterone Receptors
    • Teutsch, G.; Klich, M.; Bouchoux, F.; Gerede, E.; Philibert, D. Synthesis of a Fluorescent Steroid Derivative with High Affinities for the Glucocorticoid and Progesterone Receptors. Steroids 1994, 59, 22-26.
    • (1994) Steroids , vol.59 , pp. 22-26
    • Teutsch, G.1    Klich, M.2    Bouchoux, F.3    Gerede, E.4    Philibert, D.5
  • 33
    • 0000959387 scopus 로고
    • Intramolecularly Coordinated Arylmagnesium Compounds: Effects on the Schlenk Equilibrium
    • Markies, P. R.; Altink, R. M.; Villena, A.; Akkerman, O. S.; Bickelhaupt, F. Intramolecularly Coordinated Arylmagnesium Compounds: Effects on the Schlenk Equilibrium. J. Organomet. Chem. 1991, 402, 289-312.
    • (1991) J. Organomet. Chem. , vol.402 , pp. 289-312
    • Markies, P.R.1    Altink, R.M.2    Villena, A.3    Akkerman, O.S.4    Bickelhaupt, F.5
  • 35
    • 33751385931 scopus 로고
    • Introduction of the 2-(Phenylthio)ethyl, 2-(Phenylsulfinyl)ethyl, and 2,2-Bis(phenylthio)ethyl Substitutents into Cyclic Ketones
    • Montgomery, J.; Overman, L. E. Introduction of the 2-(Phenylthio)ethyl, 2-(Phenylsulfinyl)ethyl, and 2,2-Bis(phenylthio)ethyl Substitutents into Cyclic Ketones. J. Org. Chem. 1993, 58, 6476-6479.
    • (1993) J. Org. Chem. , vol.58 , pp. 6476-6479
    • Montgomery, J.1    Overman, L.E.2


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