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Volumn 12, Issue 13, 2004, Pages 3497-3502

Synthesis and antileishmanial activity of novel buparvaquone oxime derivatives

Author keywords

Buparvaquone; Leishmaniasis; Nitric oxide; Oxime; Prodrug

Indexed keywords

3 (4 TERT BUTYLCYCLOHEXYLMETHYL) 2 HYDROXY[1,4]NAPHTHOQUINON 1 (O METHOXIME); 3 (4 TERT BUTYLCYCLOHEXYLMETHYL) 2 HYDROXY[1,4]NAPHTHOQUINON 1 OXIME; 3 (4 TERT BUTYLCYCLOHEXYLMETHYL) 2 METHOXY[1,4]NAPHTHOQUINON 1 OXIME; 3 (4 TERT BUTYLCYCLOHEXYLMETHYL) 2 METHOXY[1,4]NAPHTHOQUINONE; ANTILEISHMANIAL AGENT; BUPARVAQUONE; UNCLASSIFIED DRUG;

EID: 2942601915     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.04.032     Document Type: Article
Times cited : (32)

References (32)
  • 1
    • 0030940539 scopus 로고    scopus 로고
    • Human Leishmaniasis. Clinical, Diagnostic, and Chemotherapeutic Developments in the Last 10 Years
    • Berman J.D. Human Leishmaniasis. Clinical, Diagnostic, and Chemotherapeutic Developments in the Last 10 Years. Clin. Infect. Dis. 24:1997;684-703
    • (1997) Clin. Infect. Dis. , vol.24 , pp. 684-703
    • Berman, J.D.1
  • 2
  • 4
    • 0022998166 scopus 로고
    • In vitro Activity of 2-Cycloalkyl-3-Hydroxy-1,4-Naphthoquinones against Theileria, Eimeria and Plasmodia Species
    • Hudson A.T., Pether M.J., Randall A.W., Fry M., Latter V.S., McHardy N. In vitro Activity of 2-Cycloalkyl-3-Hydroxy-1, 4-Naphthoquinones against Theileria, Eimeria and Plasmodia Species. Eur. J. Med. Chem. Chim. Ther. 21:1986;271-275
    • (1986) Eur. J. Med. Chem. Chim. Ther. , vol.21 , pp. 271-275
    • Hudson, A.T.1    Pether, M.J.2    Randall, A.W.3    Fry, M.4    Latter, V.S.5    McHardy, N.6
  • 5
    • 0022364492 scopus 로고
    • The Activity of Plumbagin and Other Electron Carriers Against Leishmania Donovani and Leishmania Mexicana Amazonensis
    • Croft S.L., Evans A.T., Neal R.A. The Activity of Plumbagin and Other Electron Carriers Against Leishmania Donovani and Leishmania Mexicana Amazonensis. Ann. Trop. Med. Parasitol. 79:1985;651-653
    • (1985) Ann. Trop. Med. Parasitol. , vol.79 , pp. 651-653
    • Croft, S.L.1    Evans, A.T.2    Neal, R.A.3
  • 8
    • 0035865881 scopus 로고    scopus 로고
    • 2- and 3-Substituted 1,4-Naphthoquinone Derivatives as Subversive Substrates of Trypanothione Reductase and Lipoamide Dehydrogenase from Trypanosoma Cruzi: Synthesis and Correlation between Redox Cycling Activities and in Vitro Cytotoxicity
    • Salmon-Chemin L., Buisine E., Yardley V., Kohler S., Debreu M.A., Landry V., Sergheraert C., Croft S.L., Krauth-Siegel R.L., Davioud-Charvet E. 2- and 3-Substituted 1, 4-Naphthoquinone Derivatives as Subversive Substrates of Trypanothione Reductase and Lipoamide Dehydrogenase from Trypanosoma Cruzi: Synthesis and Correlation between Redox Cycling Activities and In Vitro Cytotoxicity. J. Med. Chem. 44:2001;548-565
    • (2001) J. Med. Chem. , vol.44 , pp. 548-565
    • Salmon-Chemin, L.1    Buisine, E.2    Yardley, V.3    Kohler, S.4    Debreu, M.A.5    Landry, V.6    Sergheraert, C.7    Croft, S.L.8    Krauth-Siegel, R.L.9    Davioud-Charvet, E.10
  • 9
    • 0028101772 scopus 로고
    • Coenzyme Q. Homologs in Parasitic Protozoa as Targets for Chemotherapeutic Attack
    • Ellis J.E. Coenzyme Q. Homologs in Parasitic Protozoa as Targets for Chemotherapeutic Attack. Parasitol. Today. 10:1994;296-301
    • (1994) Parasitol. Today , vol.10 , pp. 296-301
    • Ellis, J.E.1
  • 10
    • 0026040838 scopus 로고
    • Molecular Mechanisms of Quinone Cytotoxicity
    • O'Brien P.J. Molecular Mechanisms of Quinone Cytotoxicity. Chem. Biol. Interact. 80:1991;1-41
    • (1991) Chem. Biol. Interact. , vol.80 , pp. 1-41
    • O'Brien, P.J.1
  • 11
    • 0031940263 scopus 로고    scopus 로고
    • The Immune Response to Leishmania: Mechanisms of Parasite Control and Evasion
    • Bogdan C., Rollinghoff M. The Immune Response to Leishmania: Mechanisms of Parasite Control and Evasion. Int. J. Parasitol. 28:1998;121-134
    • (1998) Int. J. Parasitol. , vol.28 , pp. 121-134
    • Bogdan, C.1    Rollinghoff, M.2
  • 12
    • 0033557291 scopus 로고    scopus 로고
    • Macrophage Microbicidal Mechanisms in Vivo: Reactive Nitrogen Versus Oxygen Intermediates in the Killing of Intracellular Visceral Leishmania Donovani
    • Murray H.W., Nathan C.F. Macrophage Microbicidal Mechanisms In Vivo: Reactive Nitrogen Versus Oxygen Intermediates in the Killing of Intracellular Visceral Leishmania Donovani. J. Exp. Med. 189:1999;741-746
    • (1999) J. Exp. Med. , vol.189 , pp. 741-746
    • Murray, H.W.1    Nathan, C.F.2
  • 14
    • 0025883342 scopus 로고
    • Nitric Oxide: Physiology, Pathophysiology, and Pharmacology
    • Moncada S., Palmer R.M., Higgs E.A. Nitric Oxide: Physiology, Pathophysiology, and Pharmacology. Pharmacol. Rev. 43:1991;109-142
    • (1991) Pharmacol. Rev. , vol.43 , pp. 109-142
    • Moncada, S.1    Palmer, R.M.2    Higgs, E.A.3
  • 15
    • 0028924114 scopus 로고
    • Formation of Nitrogen Oxides Including NO from Oxidative Cleavage of C=N(OH) Bonds: A General Cytochrome P450-Dependent Reaction
    • Jousserandot A., Boucher J.L., Desseaux C., Delaforge M., Mansuy D. Formation of Nitrogen Oxides Including NO from Oxidative Cleavage of C=N(OH) Bonds: A General Cytochrome P450-Dependent Reaction. Bioorg. Med. Chem. Lett. 5:1995;423-426
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 423-426
    • Jousserandot, A.1    Boucher, J.L.2    Desseaux, C.3    Delaforge, M.4    Mansuy, D.5
  • 16
    • 0032497909 scopus 로고    scopus 로고
    • Microsomal Cytochrome P450 Dependent Oxidation of N-Hydroxyguanidines, Amidoximes, and Ketoximes: Mechanism of the Oxidative Cleavage of Their C=N(OH) Bond with Formation of Nitrogen Oxides
    • Jousserandot A., Boucher J.L., Henry Y., Niklaus B., Clement B., Mansuy D. Microsomal Cytochrome P450 Dependent Oxidation of N-Hydroxyguanidines, Amidoximes, and Ketoximes: Mechanism of the Oxidative Cleavage of Their C=N(OH) Bond with Formation of Nitrogen Oxides. Biochemistry. 37:1998;17179-17191
    • (1998) Biochemistry , vol.37 , pp. 17179-17191
    • Jousserandot, A.1    Boucher, J.L.2    Henry, Y.3    Niklaus, B.4    Clement, B.5    Mansuy, D.6
  • 17
    • 0028278433 scopus 로고
    • N-Hydroxylation of the Antiprotozoal Drug Pentamidine Catalyzed by Rabbit Liver Cytochrome P-450 2C3 or Human Liver Microsomes, Microsomal Retroreduction, and Further Oxidative Transformation of the Formed Amidoximes. Possible Relationship to the Biological Oxidation of Arginine to Ng-Hydroxyarginine, Citrulline, and Nitric Oxide
    • Clement B., Jung F. N-Hydroxylation of the Antiprotozoal Drug Pentamidine Catalyzed by Rabbit Liver Cytochrome P-450 2C3 or Human Liver Microsomes, Microsomal Retroreduction, and Further Oxidative Transformation of the Formed Amidoximes. Possible Relationship to the Biological Oxidation of Arginine to Ng-Hydroxyarginine, Citrulline, and Nitric Oxide. Drug Metab. Dispos. 22:1994;486-497
    • (1994) Drug Metab. Dispos. , vol.22 , pp. 486-497
    • Clement, B.1    Jung, F.2
  • 18
    • 0034898074 scopus 로고    scopus 로고
    • Oxidation of the Ketoxime Acetoxime to Nitric Oxide by Oxygen Radical-Generating Systems
    • Caro A.A., Cederbaum A.I., Stoyanovsky D.A. Oxidation of the Ketoxime Acetoxime to Nitric Oxide by Oxygen Radical-Generating Systems. Nitric Oxide. 5:2001;413-424
    • (2001) Nitric Oxide , vol.5 , pp. 413-424
    • Caro, A.A.1    Cederbaum, A.I.2    Stoyanovsky, D.A.3
  • 19
    • 0032796551 scopus 로고    scopus 로고
    • Transannular Interactions in Difunctional Medium Rings, 9. Spectroscopic and Theoretical Investigations of Bicyclic Dioximes and Dimethoximes with Eight-Membered Rings
    • Strenge A., Rademacher P. Transannular Interactions in Difunctional Medium Rings, 9. Spectroscopic and Theoretical Investigations of Bicyclic Dioximes and Dimethoximes with Eight-Membered Rings. Eur. J. Org. Chem. 1999;1611-1617
    • (1999) Eur. J. Org. Chem. , pp. 1611-1617
    • Strenge, A.1    Rademacher, P.2
  • 20
    • 0032811081 scopus 로고    scopus 로고
    • Transannular Interactions in Difunctional Medium Rings, 8. Spectroscopic and Theoretical Investigations of Monocyclic Dioximes and Dimethoximes with Six-, Eight, and Ten-Membered Rings
    • Strenge A., Rademacher P. Transannular Interactions in Difunctional Medium Rings, 8. Spectroscopic and Theoretical Investigations of Monocyclic Dioximes and Dimethoximes with Six-, Eight, and Ten-Membered Rings. Eur. J. Org. Chem. 1999;1601-1609
    • (1999) Eur. J. Org. Chem. , pp. 1601-1609
    • Strenge, A.1    Rademacher, P.2
  • 21
    • 0038498482 scopus 로고
    • Synthesis of 2,5-Disubstituted 3,6-Diamino-1,4-Enzoquinones
    • Hegedus L.S., Odle R.R., Winton P.M., Weider P.R. Synthesis of 2, 5-Disubstituted 3, 6-Diamino-1, 4-Enzoquinones. J. Org. Chem. 47:1982;2607-2613
    • (1982) J. Org. Chem. , vol.47 , pp. 2607-2613
    • Hegedus, L.S.1    Odle, R.R.2    Winton, P.M.3    Weider, P.R.4
  • 22
    • 0029069037 scopus 로고
    • Ocular Delivery of the Beta-Adrenergic Antagonist Alprenolol by Sequential Bioactivation of its Methoxime Analogue
    • Prokai L., Wu W.M., Somogyi G., Bodor N. Ocular Delivery of the Beta-Adrenergic Antagonist Alprenolol by Sequential Bioactivation of its Methoxime Analogue. J. Med. Chem. 38:1995;2018-2020
    • (1995) J. Med. Chem. , vol.38 , pp. 2018-2020
    • Prokai, L.1    Wu, W.M.2    Somogyi, G.3    Bodor, N.4
  • 23
    • 0029739039 scopus 로고    scopus 로고
    • Degradation Kinetics and Isomerization of Cefdinir, a New Oral Cephalosporin in Aqueous Solution. 1
    • Okamoto Y., Kiriyama K., Namiki Y., Matsushita J., Fujioka M., Yasuda T. Degradation Kinetics and Isomerization of Cefdinir, a New Oral Cephalosporin in Aqueous Solution. 1. J. Pharm. Sci. 85:1996;976-983
    • (1996) J. Pharm. Sci. , vol.85 , pp. 976-983
    • Okamoto, Y.1    Kiriyama, K.2    Namiki, Y.3    Matsushita, J.4    Fujioka, M.5    Yasuda, T.6
  • 25
    • 0000602498 scopus 로고
    • Oxidation of Aryloxyaminoalcohols with Activated Dimethylsulfoxide; A Novel C-N Oxidation Facilitated by Neighboring Group Effect
    • Simay A., Prokai L., Bodor N. Oxidation of Aryloxyaminoalcohols with Activated Dimethylsulfoxide; a Novel C-N Oxidation Facilitated by Neighboring Group Effect. Tetrahedron. 45:1989;4091-4102
    • (1989) Tetrahedron , vol.45 , pp. 4091-4102
    • Simay, A.1    Prokai, L.2    Bodor, N.3
  • 27
  • 31
    • 78651165715 scopus 로고
    • The Carbon Monoxide-Binding Pigment of Liver Microsomes. I. Evidence for Its Hemoprotein Nature
    • Omura T., Sato R. The Carbon Monoxide-Binding Pigment of Liver Microsomes. I. Evidence for Its Hemoprotein Nature. J. Biol. Chem. 239:1964;2370-2378
    • (1964) J. Biol. Chem. , vol.239 , pp. 2370-2378
    • Omura, T.1    Sato, R.2
  • 32
    • 0002469442 scopus 로고    scopus 로고
    • Determination of Nitrite and Nitrate by the Griess Reaction
    • M. Feelisch, & J.S. Stamler. Chichester: Wiley
    • Schmidt H.H.H.W., Kelm M. Determination of Nitrite and Nitrate by the Griess Reaction. Feelisch M., Stamler J.S. Methods in Nitric Oxide Research. 1996;493-497 Wiley, Chichester
    • (1996) Methods in Nitric Oxide Research , pp. 493-497
    • Schmidt, H.H.H.W.1    Kelm, M.2


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