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Volumn 24, Issue 4, 2004, Pages 425-448

Synthetic peroxides as antimalarizals

Author keywords

Antimalarials; Artemisinin; SAR; Synthetic peroxides

Indexed keywords

1,2,4 TRIOXANE DERIVATIVE; ANTIMALARIAL AGENT; ARTEFLENE; ARTEMETHER; ARTEMISININ; ARTEMISININ DERIVATIVE; ARTESUNATE; DIOXANE DERIVATIVE; ENDOPEROXIDE; HERBACEOUS AGENT; PEROXIDE; UNCLASSIFIED DRUG; YINGZHAOSU;

EID: 3042613588     PISSN: 01986325     EISSN: None     Source Type: Journal    
DOI: 10.1002/med.10066     Document Type: Review
Times cited : (262)

References (130)
  • 1
    • 0037033984 scopus 로고    scopus 로고
    • The economic and social burden of malaria
    • Sachs J, Malaney P. The economic and social burden of malaria. Nature 2002;415:680-685.
    • (2002) Nature , vol.415 , pp. 680-685
    • Sachs, J.1    Malaney, P.2
  • 2
    • 0037034009 scopus 로고    scopus 로고
    • Medical need, scientific opportunity, and the drive for antimalarial drugs
    • Ridley RG. Medical need, scientific opportunity, and the drive for antimalarial drugs. Nature 2002;415:686-693.
    • (2002) Nature , vol.415 , pp. 686-693
    • Ridley, R.G.1
  • 3
    • 0021948029 scopus 로고
    • Qinghaosu (artemisinin): An antimalarial drug from China
    • Klayman DL. Qinghaosu (artemisinin): An antimalarial drug from China. Science 1985;228:1049-1055.
    • (1985) Science , vol.228 , pp. 1049-1055
    • Klayman, D.L.1
  • 4
    • 0033614329 scopus 로고    scopus 로고
    • Antimalarial drug resistance and combination chemotherapy
    • White NJ. Antimalarial drug resistance and combination chemotherapy. Phil Trans R Soc Lond B 1999;354:739-749.
    • (1999) Phil Trans R Soc Lond B , vol.354 , pp. 739-749
    • White, N.J.1
  • 5
    • 0037192926 scopus 로고    scopus 로고
    • The evolution of drug-resistant malaria: The role of drug elimination half-life
    • Hastings IM, Watkins WM, White NJ. The evolution of drug-resistant malaria: The role of drug elimination half-life. Phil Trans R Soc Lond B 2000;357:505-519.
    • (2000) Phil Trans R Soc Lond B , vol.357 , pp. 505-519
    • Hastings, I.M.1    Watkins, W.M.2    White, N.J.3
  • 6
    • 0026584198 scopus 로고
    • Stereoselective total synthesis of (+)-artemisisnin, the antimalarial constituent of Artemesia annua L.
    • Avery MA, Chong WKM, Jennings-White C. Stereoselective total synthesis of (+)-artemisisnin, the antimalarial constituent of Artemesia annua L. J Am Chem Soc 1992;114:974-979.
    • (1992) J Am Chem Soc , vol.114 , pp. 974-979
    • Avery, M.A.1    Chong, W.K.M.2    Jennings-White, C.3
  • 7
    • 0020577131 scopus 로고
    • Total synthesis of qinghaosu
    • Schmid G, Hofheinz W. Total synthesis of qinghaosu. J Am Chem Soc 1983;105:624-625.
    • (1983) J Am Chem Soc , vol.105 , pp. 624-625
    • Schmid, G.1    Hofheinz, W.2
  • 8
    • 0022635490 scopus 로고
    • Total synthesis of arteannuin and deoxyarteannuin
    • Xu XX, Zhu J, Huang DZ, Zhou WS. Total synthesis of arteannuin and deoxyarteannuin. Tetrahedron 1986;42:819-828.
    • (1986) Tetrahedron , vol.42 , pp. 819-828
    • Xu, X.X.1    Zhu, J.2    Huang, D.Z.3    Zhou, W.S.4
  • 10
    • 0035207181 scopus 로고    scopus 로고
    • Why artemisinin and certain synthetic peroxides are potent antimalarials. Implications for the mode of action
    • Jefford CW. Why artemisinin and certain synthetic peroxides are potent antimalarials. Implications for the mode of action. Curr Med Chem 2001;8:1803-1826.
    • (2001) Curr Med Chem , vol.8 , pp. 1803-1826
    • Jefford, C.W.1
  • 11
    • 0001123285 scopus 로고    scopus 로고
    • Antimalarial activity of artemisinin (qinghaosu) and related trioxanes: Mechanism(s) of action
    • Cumming JN, Ploypradith P, Posner GH. Antimalarial activity of artemisinin (qinghaosu) and related trioxanes: Mechanism(s) of action. Adv Pharm 1997;37:253-297.
    • (1997) Adv Pharm , vol.37 , pp. 253-297
    • Cumming, J.N.1    Ploypradith, P.2    Posner, G.H.3
  • 13
    • 0037021405 scopus 로고    scopus 로고
    • Artemisinin: Mechanisms of action, resistance, and toxicity
    • Meshnick SR. Artemisinin: Mechanisms of action, resistance, and toxicity. Int J Parasitol 2002;32:1655-1660.
    • (2002) Int J Parasitol , vol.32 , pp. 1655-1660
    • Meshnick, S.R.1
  • 14
    • 0030033323 scopus 로고    scopus 로고
    • The behavior of qinghaosu (artemisinin) in the presence of non-heme iron(II) and (III)
    • Haynes RK, Vonwiller SC. The behavior of qinghaosu (artemisinin) in the presence of non-heme iron(II) and (III). Tetrahedron Lett 1996;37:257-260.
    • (1996) Tetrahedron Lett , vol.37 , pp. 257-260
    • Haynes, R.K.1    Vonwiller, S.C.2
  • 15
    • 0030066679 scopus 로고    scopus 로고
    • The behavior of qinghaosu (artemisinin) in the presence of heme iron(II) and (III)
    • Haynes RK, Vonwiller SC. The behavior of qinghaosu (artemisinin) in the presence of heme iron(II) and (III). Tetrahedron Lett 1996;37:253-256.
    • (1996) Tetrahedron Lett , vol.37 , pp. 253-256
    • Haynes, R.K.1    Vonwiller, S.C.2
  • 16
    • 0030879877 scopus 로고    scopus 로고
    • Peroxidic antimalarials
    • Jefford CW. Peroxidic antimalarials. Adv Drug Res 1997;29:271-325.
    • (1997) Adv Drug Res , vol.29 , pp. 271-325
    • Jefford, C.W.1
  • 17
    • 0032522115 scopus 로고    scopus 로고
    • Unified mechanistic framework for the Fe(II)-induced cleavage of qinghaosu and derivatives/analogs. The first spin-trapping evidence for the previously postulated secondary C-4 radical
    • Wu WM, Wu YK, Wu YL, Yao ZJ, Zhou CM, Li Y, Shan F. Unified mechanistic framework for the Fe(II)-induced cleavage of qinghaosu and derivatives/analogs. The first spin-trapping evidence for the previously postulated secondary C-4 radical. J Am Chem Soc 1998;120:3316-3325.
    • (1998) J Am Chem Soc , vol.120 , pp. 3316-3325
    • Wu, W.M.1    Wu, Y.K.2    Wu, Y.L.3    Yao, Z.J.4    Zhou, C.M.5    Li, Y.6    Shan, F.7
  • 19
    • 0032969901 scopus 로고    scopus 로고
    • Current progress in the chemistry, medicinal chemistry, and drug design of artemisinin based antimalarials
    • Vroman JA, Alvim-Gaston M, Avery MA. Current progress in the chemistry, medicinal chemistry, and drug design of artemisinin based antimalarials. Curr Pharm Des 1999;5:101-138.
    • (1999) Curr Pharm Des , vol.5 , pp. 101-138
    • Vroman, J.A.1    Alvim-Gaston, M.2    Avery, M.A.3
  • 20
    • 0033554788 scopus 로고    scopus 로고
    • Current status of artemisinin and its derivatives as antimalarial drugs
    • Dhingra V, Vishweshwar RK, Lakshmi NM. Current status of artemisinin and its derivatives as antimalarial drugs. Life Sci 2000;66:279-300.
    • (2000) Life Sci , vol.66 , pp. 279-300
    • Dhingra, V.1    Vishweshwar, R.K.2    Lakshmi, N.M.3
  • 21
    • 0031769129 scopus 로고    scopus 로고
    • Antimalarial peroxides in the qinghaosu (artemisinin) and yingzhaosu families
    • Posner GH. Antimalarial peroxides in the qinghaosu (artemisinin) and yingzhaosu families. Exp Opin Ther Patents 1998;8:1487-1494.
    • (1998) Exp Opin Ther Patents , vol.8 , pp. 1487-1494
    • Posner, G.H.1
  • 22
    • 0036009409 scopus 로고    scopus 로고
    • From mechanistic studies on artemisinin derivatives to new modular antimalarial drugs
    • Robert A, Dechy-Cabaret O, Cazelles J, Meunier B. From mechanistic studies on artemisinin derivatives to new modular antimalarial drugs. Acc Chem Res 2002;35:167-174.
    • (2002) Acc Chem Res , vol.35 , pp. 167-174
    • Robert, A.1    Dechy-Cabaret, O.2    Cazelles, J.3    Meunier, B.4
  • 24
    • 0036546934 scopus 로고    scopus 로고
    • Synthesis and antimalarial activity of 1,2,4,5-tetraoxanes
    • Dong Y. Synthesis and antimalarial activity of 1,2,4,5-tetraoxanes. Mini-Rev Med Chem 2002;2:113-123.
    • (2002) Mini-Rev Med Chem , vol.2 , pp. 113-123
    • Dong, Y.1
  • 25
    • 0037021402 scopus 로고    scopus 로고
    • Antimalarial chemotherapeutic peroxides: Artemisinin, yingzhaosu A, and related compounds
    • Borstnik K, Paik I-H, Shapiro TA, Posner GH. Antimalarial chemotherapeutic peroxides: Artemisinin, yingzhaosu A, and related compounds. Int J Parasitol 2002;32:1661-1667.
    • (2002) Int J Parasitol , vol.32 , pp. 1661-1667
    • Borstnik, K.1    Paik, I.-H.2    Shapiro, T.A.3    Posner, G.H.4
  • 28
    • 0038440391 scopus 로고    scopus 로고
    • A short synthesis and biological evaluation of potent and nontoxic antimalarial bridged bicyclic β-sulfonyl-endoperoxides
    • Bachi MD, Korshin EE, Hoos R, Szpilman AM, Ploypradith P, Xie S, Shapiro TA, Posner GH. A short synthesis and biological evaluation of potent and nontoxic antimalarial bridged bicyclic β-sulfonyl-endoperoxides. J Med Chem 2003;46:2516-2533.
    • (2003) J Med Chem , vol.46 , pp. 2516-2533
    • Bachi, M.D.1    Korshin, E.E.2    Hoos, R.3    Szpilman, A.M.4    Ploypradith, P.5    Xie, S.6    Shapiro, T.A.7    Posner, G.H.8
  • 31
    • 0018661768 scopus 로고
    • Summary of the research of Chinese traditional and herbal medicines
    • Department of Phytochemistry, Institute of Materia Medica, Chinese Academy of Medical Sciences. Summary of the research of Chinese traditional and herbal medicines. Acta Pharm Sinica 1979;14:746-768.
    • (1979) Acta Pharm Sinica , vol.14 , pp. 746-768
  • 33
    • 0028088750 scopus 로고
    • Antimalarial activity of the bicyclic peroxide Ro 42-1611 (arteflene) in experimental models
    • Jaquet C, Stohler HR, Chollet J, Peters W. Antimalarial activity of the bicyclic peroxide Ro 42-1611 (arteflene) in experimental models. Trop Med Parasitol 1994;45:266-271.
    • (1994) Trop Med Parasitol , vol.45 , pp. 266-271
    • Jaquet, C.1    Stohler, H.R.2    Chollet, J.3    Peters, W.4
  • 37
    • 0037128466 scopus 로고    scopus 로고
    • An efficient synthesis of bridged-bicyclic peroxides structurally related to antimalarial yingzhaosu A based on radical cooxygenation of thiols and monoterpenes
    • Korshin EE, Hoos R, Szpilman AM, Konstantinovski L, Posner GH, Bachi MD. An efficient synthesis of bridged-bicyclic peroxides structurally related to antimalarial yingzhaosu A based on radical cooxygenation of thiols and monoterpenes. Tetrahedron 2002;58:2449-2469.
    • (2002) Tetrahedron , vol.58 , pp. 2449-2469
    • Korshin, E.E.1    Hoos, R.2    Szpilman, A.M.3    Konstantinovski, L.4    Posner, G.H.5    Bachi, M.D.6
  • 38
    • 0000015486 scopus 로고    scopus 로고
    • Thiol-oxygen cooxidation of monoterpenes. Synthesis of endoperoxides structurally related to antimalarial yingzhaosu A
    • Bachi MD, Korshin EE. Thiol-oxygen cooxidation of monoterpenes. Synthesis of endoperoxides structurally related to antimalarial yingzhaosu A. Synlett 1998;122-124.
    • (1998) Synlett , pp. 122-124
    • Bachi, M.D.1    Korshin, E.E.2
  • 43
    • 0037060948 scopus 로고    scopus 로고
    • Synthesis, Fe(II)-induced degradation, and antimalarial activities of 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes: Direct evidence for nucleophilic O-1,2-aryl shifts
    • Kamata M, Ohta M, Komatsu K, Kim HS, Wataya Y. Synthesis, Fe(II)-induced degradation, and antimalarial activities of 1,5-diaryl-6,7-dioxabicyclo[3.2.2] nonanes: Direct evidence for nucleophilic O-1,2-aryl shifts. Tetrahedron Lett 2002;43:2063-2067.
    • (2002) Tetrahedron Lett , vol.43 , pp. 2063-2067
    • Kamata, M.1    Ohta, M.2    Komatsu, K.3    Kim, H.S.4    Wataya, Y.5
  • 45
    • 12444296964 scopus 로고    scopus 로고
    • Synthesis and antimalarial activity of heteroatom-containing bicyclic endoperoxides
    • Posner GH, Gonzalez L, Cumming JN, Klinedinst D, Shapiro TA. 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
  • 48
    • 0022370903 scopus 로고
    • Antimalarial agents. 1. α-Santonin-derived cyclic peroxide as potential antimalarial agent
    • Tani S, Fukamiya N, Kiyokawa H, Musallam HA, Pick RO, Lee KH. Antimalarial agents. 1. α-Santonin-derived cyclic peroxide as potential antimalarial agent. J Med Chem 1985;28:1743-1744.
    • (1985) J Med Chem , vol.28 , pp. 1743-1744
    • Tani, S.1    Fukamiya, N.2    Kiyokawa, H.3    Musallam, H.A.4    Pick, R.O.5    Lee, K.H.6
  • 50
    • 0034701597 scopus 로고    scopus 로고
    • Synthesis and anti-malarial activity of yingzhaosu A analogs from unsaturated hydroperoxy acetals
    • Tokuyasu T, Masuyama A, Nojima M, Kim HS, Wataya Y. Synthesis and anti-malarial activity of yingzhaosu A analogs from unsaturated hydroperoxy acetals. Tetrahedron Lett 2000;41:3145-3148.
    • (2000) Tetrahedron Lett , vol.41 , pp. 3145-3148
    • Tokuyasu, T.1    Masuyama, A.2    Nojima, M.3    Kim, H.S.4    Wataya, Y.5
  • 51
    • 0035833052 scopus 로고    scopus 로고
    • Yingzhaosu A analogues: Synthesis by the ozonolysis of unsaturated hydroperoxides, structural analysis, and determination of antimalarial activity
    • Tokuyasu T, Masuyama A, Nojima M, McCullough KJ, Kim HS, Wataya Y. Yingzhaosu A analogues: Synthesis by the ozonolysis of unsaturated hydroperoxides, structural analysis, and determination of antimalarial activity. Tetrahedron 2001;57:5979-5989.
    • (2001) Tetrahedron , vol.57 , pp. 5979-5989
    • Tokuyasu, T.1    Masuyama, A.2    Nojima, M.3    McCullough, K.J.4    Kim, H.S.5    Wataya, Y.6
  • 52
    • 0004733836 scopus 로고    scopus 로고
    • An antimalarially active cyclic peroxy ketal
    • Posner GH, O'Dowd H, An antimalarially active cyclic peroxy ketal. Heterocycles 1998;47:643-646.
    • (1998) Heterocycles , vol.47 , pp. 643-646
    • Posner, G.H.1    O'Dowd, H.2
  • 55
    • 0038101523 scopus 로고    scopus 로고
    • 1,4-Dihydroxy-2,3-dioxatricyclo[8.4.0.0.4.9]tetradecane and derivatives with in vitro activity against Plasmodium falciparum, Trypanasoma b brucei, Trypanasoma cruzi, and Leishmaniasis infantum
    • Howarth J, Wilson D. 1,4-Dihydroxy-2,3-dioxatricyclo[8.4.0.0.4.9] tetradecane and derivatives with in vitro activity against Plasmodium falciparum, Trypanasoma b brucei, Trypanasoma cruzi, and Leishmaniasis infantum. Bioorg Med Chem Lett 2003;13:2013-2015.
    • (2003) Bioorg Med Chem Lett , vol.13 , pp. 2013-2015
    • Howarth, J.1    Wilson, D.2
  • 57
    • 0027183983 scopus 로고
    • Synthesis and antimalarial evaluation of 2,3,5-trioxabicyclo[2.2.3] nonane, a model for the putative pharmacophore of artemisinin
    • Casteel DA, Peri SP, Gerena L. Synthesis and antimalarial evaluation of 2,3,5-trioxabicyclo[2.2.3]nonane, a model for the putative pharmacophore of artemisinin. Bioorg Med Chem Lett 1993;3:1707-1710.
    • (1993) Bioorg Med Chem Lett , vol.3 , pp. 1707-1710
    • Casteel, D.A.1    Peri, S.P.2    Gerena, L.3
  • 58
    • 0026674545 scopus 로고
    • Synthesis and antimalarial evaluation of 2,3,5-trioxabicyclo[2.2.2] octanes, models for the putative pharmacophore of qinghaosu (artemisinin)
    • Casteel DA, Jung KE, Gernea L, Milhous W. Synthesis and antimalarial evaluation of 2,3,5-trioxabicyclo[2.2.2]octanes, models for the putative pharmacophore of qinghaosu (artemisinin). Bioorg Med Chem Lett 1992;2:623-626.
    • (1992) Bioorg Med Chem Lett , vol.2 , pp. 623-626
    • Casteel, D.A.1    Jung, K.E.2    Gernea, L.3    Milhous, W.4
  • 60
    • 0025882928 scopus 로고
    • Olefin oxidative cleavage and dioxetane formation using triethylsilyl hydrotrioxide: Applications to preparation of potent antimalarial 1,2,4-trioxanes
    • Posner GH, Oh CH, Milhous WK. Olefin oxidative cleavage and dioxetane formation using triethylsilyl hydrotrioxide: Applications to preparation of potent antimalarial 1,2,4-trioxanes. Tetrahedron Lett 1991;32:4235-4238.
    • (1991) Tetrahedron Lett , vol.32 , pp. 4235-4238
    • Posner, G.H.1    Oh, C.H.2    Milhous, W.K.3
  • 61
    • 0032510451 scopus 로고    scopus 로고
    • Orally active antimalarial 3-substituted trioxanes: New synthetic methodology and biological evaluation
    • Posner GH, Cumming JN, Woo SH, Ploypradith P, Xie S, Shapiro TA. Orally active antimalarial 3-substituted trioxanes: New synthetic methodology and biological evaluation. J Med Chem 1998;41:940-951.
    • (1998) J Med Chem , vol.41 , pp. 940-951
    • Posner, G.H.1    Cumming, J.N.2    Woo, S.H.3    Ploypradith, P.4    Xie, S.5    Shapiro, T.A.6
  • 64
  • 66
    • 0026635291 scopus 로고
    • Extraordinarily potent antimalarial compounds: New, structurally simple, easily synthesized, tricyclic 1,2,4-trioxanes
    • Posner GH, Oh CH, Gerena L, Milhous WK. Extraordinarily potent antimalarial compounds: New, structurally simple, easily synthesized, tricyclic 1,2,4-trioxanes. J Med Chem 1992;35:2459-2467.
    • (1992) J Med Chem , vol.35 , pp. 2459-2467
    • Posner, G.H.1    Oh, C.H.2    Gerena, L.3    Milhous, W.K.4
  • 67
    • 0029061802 scopus 로고
    • Structure-activity relationships of lactone ring-opened analogs of the antimalarial 1,2,4-trioxane artemisinin
    • Posner GH, McGarvey DJ, Oh CH, Kumar N, Meshnick SR, Asawamahasadka W. Structure-activity relationships of lactone ring-opened analogs of the antimalarial 1,2,4-trioxane artemisinin. J Med Chem 1995;38:607-612.
    • (1995) J Med Chem , vol.38 , pp. 607-612
    • Posner, G.H.1    McGarvey, D.J.2    Oh, C.H.3    Kumar, N.4    Meshnick, S.R.5    Asawamahasadka, W.6
  • 68
    • 0032510380 scopus 로고    scopus 로고
    • Design, synthesis, derivatization, and structure-activity relationships of simplified, tricyclic, 1,2,4-trioxane alcohol analogs of the antimalarial artemisinin
    • Cumming JN, Wang D, Park SB, Shapiro TA, Posner GH. Design, synthesis, derivatization, and structure-activity relationships of simplified, tricyclic, 1,2,4-trioxane alcohol analogs of the antimalarial artemisinin. J Med Chem 1998;41:952-964.
    • (1998) J Med Chem , vol.41 , pp. 952-964
    • Cumming, J.N.1    Wang, D.2    Park, S.B.3    Shapiro, T.A.4    Posner, G.H.5
  • 69
  • 70
    • 0037039929 scopus 로고    scopus 로고
    • Alkylating capacity and reaction products of antimalarial trioxanes after activation by a heme model
    • Cazelles J, Robert A, Meunier B. Alkylating capacity and reaction products of antimalarial trioxanes after activation by a heme model. J Org Chem 2002;67:609-619.
    • (2002) J Org Chem , vol.67 , pp. 609-619
    • Cazelles, J.1    Robert, A.2    Meunier, B.3
  • 72
    • 0035855920 scopus 로고    scopus 로고
    • Antimalarial simplified 3-aryltrioxanes: Synthesis and preclinical efficacy/toxicity testing in rodents
    • Posner GH, Jeon HB, Parker MH, Krasavin M, Paik IH, Shapiro TA. Antimalarial simplified 3-aryltrioxanes: Synthesis and preclinical efficacy/toxicity testing in rodents. J Med Chem 2001;44:3054-3058.
    • (2001) J Med Chem , vol.44 , pp. 3054-3058
    • Posner, G.H.1    Jeon, H.B.2    Parker, M.H.3    Krasavin, M.4    Paik, I.H.5    Shapiro, T.A.6
  • 73
    • 0037194666 scopus 로고    scopus 로고
    • Orally active, water-soluble antimalarial 3-aryltrioxanes: Short synthesis and preclinical efficacy testing in rodents
    • Posner GH, Jeon HB, Ploypradith P, Paik IH, Borstnik K, Xie S, Shapiro TA. Orally active, water-soluble antimalarial 3-aryltrioxanes: Short synthesis and preclinical efficacy testing in rodents. J Med Chem 2002;45:3824-3828.
    • (2002) J Med Chem , vol.45 , pp. 3824-3828
    • Posner, G.H.1    Jeon, H.B.2    Ploypradith, P.3    Paik, I.H.4    Borstnik, K.5    Xie, S.6    Shapiro, T.A.7
  • 75
    • 2742592785 scopus 로고
    • Reactions of cyclic peroxides with aldehydes and ketones catalyzed by trimethylsilyl trifluoromethanesulfonate. An efficient synthesis of 1,2,4-trioxanes
    • Jefford CW, Boukouvalas J, Kohmoto S. Reactions of cyclic peroxides with aldehydes and ketones catalyzed by trimethylsilyl trifluoromethanesulfonate. An efficient synthesis of 1,2,4-trioxanes. J Chem Soc Chem Commun 1984;523-524.
    • (1984) J Chem Soc Chem Commun , pp. 523-524
    • Jefford, C.W.1    Boukouvalas, J.2    Kohmoto, S.3
  • 76
    • 0027280239 scopus 로고
    • The chemotherapy of rodent malaria. XLIX. The activities of some synthetic 1,2,4-trioxanes against chloroquine-sensitive and chloroquine- resistant parasites. Part 2: Structure-activity studies on cis-fused cyclopenteno-1,2,4-trioxanes (fenozans) against drug-sensitive and drug-resistant lines of Plasmodium berghei and P. yoelii ssp. NS in vivo
    • Peters W, Robinson BL, Rossier JC, Misra D, Jefford CW, Rossier JC. The chemotherapy of rodent malaria. XLIX. The activities of some synthetic 1,2,4-trioxanes against chloroquine-sensitive and chloroquine-resistant parasites. Part 2: Structure-activity studies on cis-fused cyclopenteno-1,2,4- trioxanes (fenozans) against drug-sensitive and drug-resistant lines of Plasmodium berghei and P. yoelii ssp. NS in vivo. Ann Trop Med Parasitol 1993;87:9-16.
    • (1993) Ann Trop Med Parasitol , vol.87 , pp. 9-16
    • Peters, W.1    Robinson, B.L.2    Rossier, J.C.3    Misra, D.4    Jefford, C.W.5    Rossier, J.C.6
  • 77
    • 0034163723 scopus 로고    scopus 로고
    • The structure and anfimalarial activity of some 1,2,4-trioxanes, 1,2,4,5-tetroxanes, and bicyclic endoperoxides. Implications for the mode of action
    • Jefford CW, Rossier JC, Milhous WK. The structure and anfimalarial 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.
    • (2000) Heterocycles , vol.52 , pp. 1345-1352
    • Jefford, C.W.1    Rossier, J.C.2    Milhous, W.K.3
  • 80
    • 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 BL, Rossier 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 Trop Med Parasitol 1993;87:1-7.
    • (1993) Ann Trop Med Parasitol , vol.87 , pp. 1-7
    • Peters, W.1    Robinson, B.L.2    Rossier, J.C.3    Jefford, C.W.4
  • 81
    • 0027263170 scopus 로고
    • The chemotherapy of rodent malaria. L. The activities of some synthetic 1,2,4-trioxanes against chloroquine-sensitive and chloroquine-resistant parasites. Part 3: Observations on 'Fenozan-50F', a difluorinated 3,3prime;-spirocyclopentane 1,2,4-trioxane
    • Peters W, Robinson BL, Tovey G, Rossier JC, Jefford CW. The chemotherapy of rodent malaria. L. The activities of some synthetic 1,2,4-trioxanes against chloroquine-sensitive and chloroquine-resistant parasites. Part 3: Observations on 'Fenozan-50F', a difluorinated 3,3′-spirocyclopentane 1,2,4-trioxane. Ann Trop Med Parasitol 1993;87:111-123.
    • (1993) Ann Trop Med Parasitol , vol.87 , pp. 111-123
    • Peters, W.1    Robinson, B.L.2    Tovey, G.3    Rossier, J.C.4    Jefford, C.W.5
  • 82
    • 0031042849 scopus 로고    scopus 로고
    • The chemotherapy of rodent malaria. LIII. 'Fenozan B07' (Fenozan-50F), a difluorinated 3,3′-spirocyclopentane 1,2,4-trioxane: Comparison with some compounds of the artemisinin series
    • Fleck SL, Robinson BL, Peters W, Thevin F, Boulard Y, Glenat C, Caillard V, Landau I. The chemotherapy of rodent malaria. LIII. 'Fenozan B07' (Fenozan-50F), a difluorinated 3,3′-spirocyclopentane 1,2,4-trioxane: Comparison with some compounds of the artemisinin series. Ann Trop Med Parasitol 1997;91:25-32.
    • (1997) Ann Trop Med Parasitol , vol.91 , pp. 25-32
    • Fleck, S.L.1    Robinson, B.L.2    Peters, W.3    Thevin, F.4    Boulard, Y.5    Glenat, C.6    Caillard, V.7    Landau, I.8
  • 83
    • 0031056405 scopus 로고    scopus 로고
    • The chemotherapy of rodent malaria. LIV. Combinations of 'Fenozan B07' (Fenozan-50F), a difluorinated 3,3′-spiorocyclopentane 1,2,4-trioxane, with other drugs against drug-sensitive and drug-resistant parasites
    • Fleck SL, Robinson BL, Peters W. The chemotherapy of rodent malaria. LIV. Combinations of 'Fenozan B07' (Fenozan-50F), a difluorinated 3,3′-spiorocyclopentane 1,2,4-trioxane, with other drugs against drug-sensitive and drug-resistant parasites. Ann Trop Med Parasitol 1997;91:33-39.
    • (1997) Ann Trop Med Parasitol , vol.91 , pp. 33-39
    • Fleck, S.L.1    Robinson, B.L.2    Peters, W.3
  • 84
    • 0037191630 scopus 로고    scopus 로고
    • Synthesis of antimalarial 1,2,4-trioxanes via photooxygenation of a chiral allylic alcohol
    • Griesbeck AG, El-Idreesy TT, Fiege M, Brun R. Synthesis of antimalarial 1,2,4-trioxanes via photooxygenation of a chiral allylic alcohol. Org Lett 2002;4:4193-4195.
    • (2002) Org Lett , vol.4 , pp. 4193-4195
    • Griesbeck, A.G.1    El-Idreesy, T.T.2    Fiege, M.3    Brun, R.4
  • 85
    • 0035797060 scopus 로고    scopus 로고
    • Regioselective Mukaiyama hydroperoxysilylation of 2-alkyl- or 2-aryl-prop-2-en-1-ols: Application to a new synthesis of 1,2,4-trioxanes
    • O'Neill PM, Pugh M, Davies J, Ward SA, Park BK. Regioselective Mukaiyama hydroperoxysilylation of 2-alkyl- or 2-aryl-prop-2-en-1-ols: Application to a new synthesis of 1,2,4-trioxanes. Tetrahedron Lett 2001;42:4569-4571.
    • (2001) Tetrahedron Lett , vol.42 , pp. 4569-4571
    • O'Neill, P.M.1    Pugh, M.2    Davies, J.3    Ward, S.A.4    Park, B.K.5
  • 86
    • 0037025438 scopus 로고    scopus 로고
    • Photo-oxygenation of geraniol: Synthesis of a novel series of hydroxy-functionalized anti-malarial 1,2,4-trioxanes
    • Singh C, Gupta N, Puri SK. Photo-oxygenation of geraniol: Synthesis of a novel series of hydroxy-functionalized anti-malarial 1,2,4-trioxanes. Bioorg Med Chem Lett 2002;12:1913-1916.
    • (2002) Bioorg Med Chem Lett , vol.12 , pp. 1913-1916
    • Singh, C.1    Gupta, N.2    Puri, S.K.3
  • 87
    • 0025027645 scopus 로고
    • Preparation of β-hydroxyhydroperoxides by photooxygenation of allylic alcohols and their elaboration into 1,2,4-trioxanes
    • Singh C. Preparation of β-hydroxyhydroperoxides by photooxygenation of allylic alcohols and their elaboration into 1,2,4-trioxanes. Tetrahedron Lett 1990;31:6901-6902.
    • (1990) Tetrahedron Lett , vol.31 , pp. 6901-6902
    • Singh, C.1
  • 89
    • 0029087357 scopus 로고
    • In vivo potent antimalarial 1,2,4-trioxanes: Synthesis and activity of 8-(α-arylvinyl)-6,7,10-trioxaspiro[4,5]decanes and 3-(α-arylvinyl)- 1,2,5-trioxaspiro[5,5]undecanes against Plasmodium berghei in mice
    • Singh C, Misra D, Saxena G, Chandra S. In vivo potent antimalarial 1,2,4-trioxanes: Synthesis and activity of 8-(α-arylvinyl)-6,7,10- trioxaspiro[4,5]decanes and 3-(α-arylvinyl)-1,2,5-trioxaspiro[5,5] undecanes against Plasmodium berghei in mice. Bioorg Med Chem Lett 1995;5:1913-1916.
    • (1995) Bioorg Med Chem Lett , vol.5 , pp. 1913-1916
    • Singh, C.1    Misra, D.2    Saxena, G.3    Chandra, S.4
  • 92
    • 37049076756 scopus 로고
    • Synthesis of steroidal 1,2,4-trioxane as potential antimalarial agent
    • Rong YJ, Wu YL. Synthesis of steroidal 1,2,4-trioxane as potential antimalarial agent. J Chem Soc [Perkin 1] 1993;2149-2150.
    • (1993) J Chem Soc [Perkin 1] , pp. 2149-2150
    • Rong, Y.J.1    Wu, Y.L.2
  • 95
    • 0032515010 scopus 로고    scopus 로고
    • Dispiro-1,2,4,5-tetraoxanes via ozonolysis of cycloalkanone O-methyl oximes: A comparison with the peroxidation of cycloalkanones in acetonitrile sulfuric acid media
    • Dong Y, Vennerstrom JL. Dispiro-1,2,4,5-tetraoxanes via ozonolysis of cycloalkanone O-methyl oximes: A comparison with the peroxidation of cycloalkanones in acetonitrile sulfuric acid media. J Org Chem 1998;63:8582-8585.
    • (1998) J Org Chem , vol.63 , pp. 8582-8585
    • Dong, Y.1    Vennerstrom, J.L.2
  • 96
    • 0033594440 scopus 로고    scopus 로고
    • Synthesis and antimalarial activity of 11 dispiro-1,2,4,5-tetraoxane analogues of WR 148999: 7,8,15,16-tetraoxadispiro[5.2.5.2]hexadecanes substituted at the I and 10 positions with unsaturated and polar functional groups
    • Dong Y, Matile H, Chollet J, Kaminsky R, Wood JK, Vennerstrom JL. Synthesis and antimalarial activity of 11 dispiro-1,2,4,5-tetraoxane analogues of WR 148999:7,8,15,16-tetraoxadispiro[5.2.5.2]hexadecanes substituted at the I and 10 positions with unsaturated and polar functional groups. J Med Chem 1999;42:1477-1480.
    • (1999) J Med Chem , vol.42 , pp. 1477-1480
    • Dong, Y.1    Matile, H.2    Chollet, J.3    Kaminsky, R.4    Wood, J.K.5    Vennerstrom, J.L.6
  • 97
    • 0033566212 scopus 로고    scopus 로고
    • Synthesis and antimalarial activity of cyclic peroxides, 1,2,4,5,7-pentoxocanes and 1,2,4,5-tetroxanes
    • Kim HS, Shibata Y, Wataya Y, Tsuchiya K, Masuyama A, Nojima M. Synthesis and antimalarial activity of cyclic peroxides, 1,2,4,5,7-pentoxocanes and 1,2,4,5-tetroxanes. J Med Chem 1999;42:2604-2609.
    • (1999) J Med Chem , vol.42 , pp. 2604-2609
    • Kim, H.S.1    Shibata, Y.2    Wataya, Y.3    Tsuchiya, K.4    Masuyama, A.5    Nojima, M.6
  • 101
    • 0030477376 scopus 로고    scopus 로고
    • Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity
    • Todorovic NM, Stefanovic M, Tinant B, Declercq JP, Makler MT, Solaja BA. Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity. Steroids 1996;61:688-696.
    • (1996) Steroids , vol.61 , pp. 688-696
    • Todorovic, N.M.1    Stefanovic, M.2    Tinant, B.3    Declercq, J.P.4    Makler, M.T.5    Solaja, B.A.6
  • 103
    • 0036377759 scopus 로고    scopus 로고
    • Antimalarial peroxides: The first intramolecular 1,2,4,5-tetraoxane
    • Opsenica D, Pocsfalvi G, Milhous WK, Solaja BA. Antimalarial peroxides: The first intramolecular 1,2,4,5-tetraoxane. J Serb Chem Soc 2002;67:465-471.
    • (2002) J Serb Chem Soc , vol.67 , pp. 465-471
    • Opsenica, D.1    Pocsfalvi, G.2    Milhous, W.K.3    Solaja, B.A.4
  • 106
    • 0034640840 scopus 로고    scopus 로고
    • Synthesis, crystal structure, and antimalarial activity of functionalized spiro-1,2,4,5-tetraoxacycloalkanes from unsaturated hydroperoxy peracetals
    • Nonami Y, Tokuyasu T, Masuyama A, Nojima M, McCullough KJ, Kim HS, Wataya Y. Synthesis, crystal structure, and antimalarial activity of functionalized spiro-1,2,4,5-tetraoxacycloalkanes from unsaturated hydroperoxy peracetals. Tetrahedron Lett 2000;41:4681-4684.
    • (2000) Tetrahedron Lett , vol.41 , pp. 4681-4684
    • Nonami, Y.1    Tokuyasu, T.2    Masuyama, A.3    Nojima, M.4    McCullough, K.J.5    Kim, H.S.6    Wataya, Y.7
  • 107
    • 0033579626 scopus 로고    scopus 로고
    • Synthesis, crystal structure, and antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes from 2,3-dihydroperoxy-2-phenylnorbornane
    • McCullough KJ, Nonami Y, Masuyama A, Nojima M, Kim HS, Wataya Y. Synthesis, crystal structure, and antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes from 2,3-dihydroperoxy-2-phenylnorbornane. Tetrahedron Lett 1999;40:9151-9155.
    • (1999) Tetrahedron Lett , vol.40 , pp. 9151-9155
    • McCullough, K.J.1    Nonami, Y.2    Masuyama, A.3    Nojima, M.4    Kim, H.S.5    Wataya, Y.6
  • 109
    • 0024489365 scopus 로고
    • Amine peroxides as potential antimalarials
    • Vennerstrom JL. Amine peroxides as potential antimalarials. J Med Chem 1989;32:64-67.
    • (1989) J Med Chem , vol.32 , pp. 64-67
    • Vennerstrom, J.L.1
  • 111
    • 0034681067 scopus 로고    scopus 로고
    • Preparation and antimalarial activities of "trioxaquines", new modular molecules with a trioxane skeleton linked to a 4-aminoquinoline
    • Dechy-Cabaret O, Benoit-Vical F, Robert A, Meunier B. Preparation and antimalarial activities of "trioxaquines", new modular molecules with a trioxane skeleton linked to a 4-aminoquinoline. Chem BioChem 2000;1:281-283.
    • (2000) Chem BioChem , vol.1 , pp. 281-283
    • Dechy-Cabaret, O.1    Benoit-Vical, F.2    Robert, A.3    Meunier, B.4
  • 112
    • 0035465508 scopus 로고    scopus 로고
    • Preparation and antimalarial activities of "trioxaquines", new modular molecules with a trioxane skeleton linked to a 4-aminoquinoline
    • Dechy-Cabaret O, Benoit-Vical F, Robert A, Meunier B. Preparation and antimalarial activities of "trioxaquines", new modular molecules with a trioxane skeleton linked to a 4-aminoquinoline. Actualite Chim 2001;9-11.
    • (2001) Actualite Chim , pp. 9-11
    • Dechy-Cabaret, O.1    Benoit-Vical, F.2    Robert, A.3    Meunier, B.4
  • 116
    • 0037075833 scopus 로고    scopus 로고
    • Synthesis and notable antimalarial activity of acyclic peroxides, 1-(alkyldioxy)-1-(methyldioxy)cyclododecanes
    • Hamada Y, Tokuhara H, Masuyama A, Nojima M, Kim HS, Ono K, Ogura N, Wataya Y. Synthesis and notable antimalarial activity of acyclic peroxides, 1-(alkyldioxy)-1-(methyldioxy)cyclododecanes. J Med Chem 2002;45:1374-1378.
    • (2002) J Med Chem , vol.45 , pp. 1374-1378
    • Hamada, Y.1    Tokuhara, H.2    Masuyama, A.3    Nojima, M.4    Kim, H.S.5    Ono, K.6    Ogura, N.7    Wataya, Y.8
  • 120
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 1997;23:3-26.
    • (1997) Adv Drug Deliv Rev , vol.23 , pp. 3-26
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 122
    • 0037468884 scopus 로고    scopus 로고
    • A comparison of physicochemical property profiles of development and marketed oral drugs
    • Wenlock MC, Austin RP, Barton P, Davis AM, Leeson PD. A comparison of physicochemical property profiles of development and marketed oral drugs. J Med Chem 2003;46:1250-1256.
    • (2003) J Med Chem , vol.46 , pp. 1250-1256
    • Wenlock, M.C.1    Austin, R.P.2    Barton, P.3    Davis, A.M.4    Leeson, P.D.5
  • 124
    • 0035953319 scopus 로고    scopus 로고
    • Property-based design: Optimization of drug absorption and pharmacokinetics
    • van de Waterbeemd H, Smith DA, Beaumont K, Walker DK. Property-based design: Optimization of drug absorption and pharmacokinetics. J Med Chem 2001;44:1313-1333.
    • (2001) J Med Chem , vol.44 , pp. 1313-1333
    • Van De Waterbeemd, H.1    Smith, D.A.2    Beaumont, K.3    Walker, D.K.4
  • 125
    • 0034890106 scopus 로고    scopus 로고
    • Optimization of metabolic stability as a goal of modern drug design
    • Thompson TN. Optimization of metabolic stability as a goal of modern drug design. Med Res Rev 2001;21:412-449.
    • (2001) Med Res Rev , vol.21 , pp. 412-449
    • Thompson, T.N.1
  • 130
    • 0031722604 scopus 로고    scopus 로고
    • Safety assessment of peroxide antimalarials: Clinical and chemical perspectives
    • Park BK, O'Neill PM, Maggs JL, Pirmohamed M. Safety assessment of peroxide antimalarials: Clinical and chemical perspectives. Br J Clin Pharmacol 1998;46:521-529.
    • (1998) Br J Clin Pharmacol , vol.46 , pp. 521-529
    • Park, B.K.1    O'Neill, P.M.2    Maggs, J.L.3    Pirmohamed, M.4


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