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Volumn 53, Issue 1, 2010, Pages 481-491

The structure - Activity relationship of the antimalarial ozonide arterolane (OZ277)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE 2 SPIRO 3' 8' [(1' PIPERAZINYLCARBONYL)METHYL] 1',2',4' TRIOXASPIRO[4.5]DECANE 4 TOSYLATE; ADAMANTANE 2 SPIRO 3' 8' [2' [[(2' AMINO 2' METHYLPROPYL)AMINO]CARBONYL]ETHYL] 1',2',4' TRIOXASPIRO[4.5]DECANE 4 TOSYLATE; ADAMANTANE 2 SPIRO 3' 8' [[(4' AMINO 1' PIPERIDINYL)CARBONYL]METHYL] 1',2',4' TRIOXASPIRO[4.5]DECANE 4 TOSYLATE; ADAMANTANE 2 SPIRO 3' 8' [[[(2' AMINO 2' METHYLPROPYL)AMINO]CARBONYL]METHYL] 1',2',4' TRIOXASPIRO[4.5]DECANE 4 TOSYLATE; ADAMANTANE 2 SPIRO 3' 8' [[[(4' AMINOCYCLOHEXYL)AMINO]CARBONYL]METHYL] 1',2',4' TRIOXASPIRO[4.5]DECANCE 4 TOSYLATE; ADAMANTANE 2 SPIRO 3' 8' [[[[(2' AMINO 2' METHYLPROPYL)AMINO]CARBONYL]OXY]METHYL] 1',2',4' TRIOXASPIRO[4.5]DECANE 4 TOSYLATE; ANTIMALARIAL AGENT; ARTESUNATE; CHLOROQUINE; CYCLOHEXANE; DISPIRO[ADAMANTANE 2,3' [1,2,4]TRIOXOLANE 5',4'' CYCLOHEXANEACETIC ACID 2 AMINO 2 METHYLPROPYLAMIDE]; FUNCTIONAL GROUP; MEFLOQUINE; OZONIDE ARTEROLANE; OZONIDE ARTEROLANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 74849086595     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm901473s     Document Type: Article
Times cited : (92)

References (44)
  • 2
    • 42349104331 scopus 로고    scopus 로고
    • (Artemisinin): The Price of Success
    • White, N. J. Qinghaosu (Artemisinin): The Price of Success. Science 2008, 320, 330-334.
    • (2008) Science , vol.320 , pp. 330-334
    • White, N.J.Q.1
  • 3
    • 84873840607 scopus 로고    scopus 로고
    • Defining and Defeating the Intolerable Burden of Malaria. III. Progress and Perspectives
    • Breman, J. G.; Alilio, M. S.; White, N. J. Defining and Defeating the Intolerable Burden of Malaria. III. Progress and Perspectives. Am. J. Trop. Med. Hyg. 2007, 77 (S6), vi-xi.
    • (2007) Am. J. Trop. Med. Hyg , vol.77 , Issue.S6
    • Breman, J.G.1    Alilio, M.S.2    White, N.J.3
  • 4
    • 2542640961 scopus 로고    scopus 로고
    • A Medicinal Chemistry Perspective on Artemisinin and Related Endoperoxides
    • O'Neill, P. M.; Posner, G. H. A Medicinal Chemistry Perspective on Artemisinin and Related Endoperoxides. J. Med. Chem. 2004, 47, 2945-2964.
    • (2004) J. Med. Chem , vol.47 , pp. 2945-2964
    • O'Neill, P.M.1    Posner, G.H.2
  • 5
    • 33646158237 scopus 로고    scopus 로고
    • From Artemisinin to New Artemisinin Antimalarials: Biosynthesis, Extraction, Old and New Derivatives, Stereochemistry and Medicinal Chemistry Requirements
    • Haynes, R. K. From Artemisinin to New Artemisinin Antimalarials: Biosynthesis, Extraction, Old and New Derivatives, Stereochemistry and Medicinal Chemistry Requirements. Curr. Top. Med. Chem. 2006, 6, 509-537.
    • (2006) Curr. Top. Med. Chem , vol.6 , pp. 509-537
    • Haynes, R.K.1
  • 6
    • 67849084837 scopus 로고    scopus 로고
    • Progress in the Development of Peroxide-based Anti-parasitic Agents
    • Muraleedharan, K. M.; Avery, M. A. Progress in the Development of Peroxide-based Anti-parasitic Agents. Drug Discovery Today 2009, 14, 793-803.
    • (2009) Drug Discovery Today , vol.14 , pp. 793-803
    • Muraleedharan, K.M.1    Avery, M.A.2
  • 7
    • 3042613588 scopus 로고    scopus 로고
    • Synthetic Peroxides as Antimalarials
    • Tang, Y.; Dong, Y.; Vennerstrom, J. L. Synthetic Peroxides as Antimalarials. Med. Res. Rev. 2004, 24, 425-448.
    • (2004) Med. Res. Rev , vol.24 , pp. 425-448
    • Tang, Y.1    Dong, Y.2    Vennerstrom, J.L.3
  • 8
    • 34249012765 scopus 로고    scopus 로고
    • New Developments in Synthetic Peroxidic Drugs as Artemisinin Mimics
    • Jefford, C. W. New Developments in Synthetic Peroxidic Drugs as Artemisinin Mimics. Drug Discovery Today 2007, 12, 487-495.
    • (2007) Drug Discovery Today , vol.12 , pp. 487-495
    • Jefford, C.W.1
  • 10
    • 67349124872 scopus 로고    scopus 로고
    • The Global Portfolio of New Antimalarial Medicines under Development
    • Olliaro, P.; Wells, T. N. C. The Global Portfolio of New Antimalarial Medicines under Development. Clin. Pharmacol. Ther. 2009, 85, 584-595.
    • (2009) Clin. Pharmacol. Ther , vol.85 , pp. 584-595
    • Olliaro, P.1    Wells, T.N.C.2
  • 11
    • 22744432838 scopus 로고    scopus 로고
    • Dong, Y.; Chollet, J.; Matile, H.; Charman, S. A.; Chiu, F. C. K.; Charman, W. N.; Scorneaux, B.; Urwyler, H.; Santo Tomas, J.; Scheurer, C.; Snyder, C.; Dorn, A.; Wang, X.; Karle, J. M.; Tang, Y.; Wittlin, S.; Brun, R.; Vennerstrom, J. L. Spiro and Dispiro-1,2,4-Trioxolanes as Antimalarial Peroxides: Charting a Workable Structure - Activity Relationship Using Simple Prototypes. J. Med. Chem. 2005, 48, 4953-4961.
    • Dong, Y.; Chollet, J.; Matile, H.; Charman, S. A.; Chiu, F. C. K.; Charman, W. N.; Scorneaux, B.; Urwyler, H.; Santo Tomas, J.; Scheurer, C.; Snyder, C.; Dorn, A.; Wang, X.; Karle, J. M.; Tang, Y.; Wittlin, S.; Brun, R.; Vennerstrom, J. L. Spiro and Dispiro-1,2,4-Trioxolanes as Antimalarial Peroxides: Charting a Workable Structure - Activity Relationship Using Simple Prototypes. J. Med. Chem. 2005, 48, 4953-4961.
  • 14
    • 33748881009 scopus 로고    scopus 로고
    • Padmanilayam, M.; Scorneaux, B.; Dong, Y.; Chollet, J.; Matile, H.; Charman, S. A.; Creek, D. J.; Charman, W. N.; Santo Tomas, J.; Scheurer, C.; Wittlin, S.; Brun, R.; Vennerstrom, J. L. Antimalarial Activity of N-Alkyl Amine, Carboxamide, Sulfonamide, and Urea Derivatives of a Dispiro-1,2,4-Trioxolane Piperidine. Bioorg. Med. Chem. Lett. 2006, 16, 5542-5545.
    • Padmanilayam, M.; Scorneaux, B.; Dong, Y.; Chollet, J.; Matile, H.; Charman, S. A.; Creek, D. J.; Charman, W. N.; Santo Tomas, J.; Scheurer, C.; Wittlin, S.; Brun, R.; Vennerstrom, J. L. Antimalarial Activity of N-Alkyl Amine, Carboxamide, Sulfonamide, and Urea Derivatives of a Dispiro-1,2,4-Trioxolane Piperidine. Bioorg. Med. Chem. Lett. 2006, 16, 5542-5545.
  • 16
    • 33748832743 scopus 로고    scopus 로고
    • Griesbaum, K.; Liu, X.; Kassiaris, A.; Scherer, M. Ozonolyses of O-Alkylated Ketoximes in the Presence of Carbonyl Groups: A Facile Access to Ozonides. Liebigs Ann./Recl. 1997, 1381-1390.
    • Griesbaum, K.; Liu, X.; Kassiaris, A.; Scherer, M. Ozonolyses of O-Alkylated Ketoximes in the Presence of Carbonyl Groups: A Facile Access to Ozonides. Liebigs Ann./Recl. 1997, 1381-1390.
  • 17
    • 0032515010 scopus 로고    scopus 로고
    • Dong, Y.; Vennerstrom, J. L. 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.
    • Dong, Y.; Vennerstrom, J. L. 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.
  • 18
    • 0001025530 scopus 로고    scopus 로고
    • Marvell, E. N.; Sturmer, D.; Rowell, C. Bicyclo[3.3.1]nonanes. A New Synthesis of 2-Bicyclo[3.3.1]-nonanone. Tetrahedron 1966, 22, 861-866.
    • Marvell, E. N.; Sturmer, D.; Rowell, C. Bicyclo[3.3.1]nonanes. A New Synthesis of 2-Bicyclo[3.3.1]-nonanone. Tetrahedron 1966, 22, 861-866.
  • 20
    • 4644291531 scopus 로고    scopus 로고
    • Synthesis of Tetrasubstituted Ozonides by the Griesbaum Coozonolysis Reaction: Diastereoselectivity and Functional Group Transformations by Post-Ozonolysis Reactions
    • Tang, Y.; Dong, Y.; Karle, J. M.; DiTusa, C. A.; Vennerstrom, J.L. Synthesis of Tetrasubstituted Ozonides by the Griesbaum Coozonolysis Reaction: Diastereoselectivity and Functional Group Transformations by Post-Ozonolysis Reactions. J. Org. Chem. 2004, 69, 6470-6473.
    • (2004) J. Org. Chem , vol.69 , pp. 6470-6473
    • Tang, Y.1    Dong, Y.2    Karle, J.M.3    DiTusa, C.A.4    Vennerstrom, J.L.5
  • 21
    • 0001250488 scopus 로고
    • Three Synthetic Routes to a Sterically Hindered Tetrazole. A New One-Step Mild Conversion of an Amide into a Tetrazole
    • Duncia, J. V.; Pierce, M. E.; Santella, J. B., III Three Synthetic Routes to a Sterically Hindered Tetrazole. A New One-Step Mild Conversion of an Amide into a Tetrazole. J. Org. Chem. 1991, 56, 2395-2400.
    • (1991) J. Org. Chem , vol.56 , pp. 2395-2400
    • Duncia, J.V.1    Pierce, M.E.2    Santella III, J.B.3
  • 22
    • 0035911001 scopus 로고    scopus 로고
    • A Simple Conversion of Amines into Monosubstituted Ureas in Organic and Aqueous Solvents
    • Liu, Q.; Luedtke, N. W.; Tor, Y. A Simple Conversion of Amines into Monosubstituted Ureas in Organic and Aqueous Solvents. Tetrahedron Lett. 2001, 42, 1445-1447.
    • (2001) Tetrahedron Lett , vol.42 , pp. 1445-1447
    • Liu, Q.1    Luedtke, N.W.2    Tor, Y.3
  • 23
    • 0242565877 scopus 로고    scopus 로고
    • Spiro and Dispiro 1,2,4-Trioxolane Antimalarials
    • U. S. Patent 6,486,199, November 26
    • Vennerstrom, J. L.; Dong, Y.; Chollet, J.; Matile, H. Spiro and Dispiro 1,2,4-Trioxolane Antimalarials. U. S. Patent 6,486,199, November 26, 2002.
    • (2002)
    • Vennerstrom, J.L.1    Dong, Y.2    Chollet, J.3    Matile, H.4
  • 24
    • 0032535563 scopus 로고    scopus 로고
    • Adang, A. E. P.; Lucas, H.; Adrianus, P. A.; de, M.; Engh, R. A.; Grootenhuis, P. D. G. Novel Acylguanidine Containing Thrombin Inhibitors With Reduced Basicity at the P1 Moiety. Bioorg. Med. Chem. Lett. 1998, 8, 3603-3608.
    • Adang, A. E. P.; Lucas, H.; Adrianus, P. A.; de, M.; Engh, R. A.; Grootenhuis, P. D. G. Novel Acylguanidine Containing Thrombin Inhibitors With Reduced Basicity at the P1 Moiety. Bioorg. Med. Chem. Lett. 1998, 8, 3603-3608.
  • 25
    • 74849129764 scopus 로고    scopus 로고
    • Activity is defined as percent reduction on day 3 postinfection compared with an untreated control group. For example, a compound with an activity of 99.9% is 10-fold more active than one with an activity of 99.0% and 100-fold more active than one with an activity of 90%.
    • Activity is defined as percent reduction on day 3 postinfection compared with an untreated control group. For example, a compound with an activity of 99.9% is 10-fold more active than one with an activity of 99.0% and 100-fold more active than one with an activity of 90%.
  • 27
    • 36149001570 scopus 로고    scopus 로고
    • Creek, D. J.; Charman, W. N.; Chiu, F. C. K.; Prankerd, R. J.; McCullough, K. J.; Dong, Y.; Vennerstrom, J. L.; Charman, S. A. Iron Mediated Degradation Kinetics of Substituted Dispiro-1,2,4-Trioxolane Antimalarials. J. Pharm. Sci. 2007, 96, 2945-2956.
    • Creek, D. J.; Charman, W. N.; Chiu, F. C. K.; Prankerd, R. J.; McCullough, K. J.; Dong, Y.; Vennerstrom, J. L.; Charman, S. A. Iron Mediated Degradation Kinetics of Substituted Dispiro-1,2,4-Trioxolane Antimalarials. J. Pharm. Sci. 2007, 96, 2945-2956.
  • 28
    • 0032733974 scopus 로고    scopus 로고
    • 9 compounds were incubated with human liver microsomes and appropriate cofactors (BD Gentest, Discovery Labware Inc., Woburn, MA) at a substrate concentration of 1-10 μM and a microsomal protein concentration of 0.4 mg/mL. Loss of parent compound was monitored by LC/MS. Extraction ratios were calculated using appropriate scaling factors as previously described by Obach, R. S. Prediction of Human Clearance of Twenty-Nine Drugs From Hepatic Microsomal Intrinsic Clearance Data: An Examination of In Vitro Half-Life Approach and Nonspecific Finding to Microsomes. Drug Metab. Dispos. 1999, 27, 1350-1359.
    • 9 compounds were incubated with human liver microsomes and appropriate cofactors (BD Gentest, Discovery Labware Inc., Woburn, MA) at a substrate concentration of 1-10 μM and a microsomal protein concentration of 0.4 mg/mL. Loss of parent compound was monitored by LC/MS. Extraction ratios were calculated using appropriate scaling factors as previously described by Obach, R. S. Prediction of Human Clearance of Twenty-Nine Drugs From Hepatic Microsomal Intrinsic Clearance Data: An Examination of In Vitro Half-Life Approach and Nonspecific Finding to Microsomes. Drug Metab. Dispos. 1999, 27, 1350-1359.
  • 29
    • 0031570357 scopus 로고    scopus 로고
    • Microtiter Plate Assays for Inhibition of Human, Drug-Metabolizing Cytochromes P450
    • Crespi, C. L.; Miller, V. P.; Penman, B. W. Microtiter Plate Assays for Inhibition of Human, Drug-Metabolizing Cytochromes P450. Anal. Biochem. 1998, 248, 188-190.
    • (1998) Anal. Biochem , vol.248 , pp. 188-190
    • Crespi, C.L.1    Miller, V.P.2    Penman, B.W.3
  • 30
    • 33751564517 scopus 로고    scopus 로고
    • Amewu, R.; Stachulski, A. V.; Ward, S. A.; Berry, N. G.; Bray, P. G.; Davies, J.; Labat, G.; Vivas, L.; O'Neill, P. M. Design and Synthesis of Orally Active Dispiro 1,2,4,5-Tetraoxanes; Synthetic Antimalarials With Superior Activity to Artemisinin. Org. Biomol. Chem. 2006, 4, 4431-4436.
    • Amewu, R.; Stachulski, A. V.; Ward, S. A.; Berry, N. G.; Bray, P. G.; Davies, J.; Labat, G.; Vivas, L.; O'Neill, P. M. Design and Synthesis of Orally Active Dispiro 1,2,4,5-Tetraoxanes; Synthetic Antimalarials With Superior Activity to Artemisinin. Org. Biomol. Chem. 2006, 4, 4431-4436.
  • 32
    • 27744592680 scopus 로고    scopus 로고
    • Enantiomeric 1,2,4-Trioxanes Display Equivalent in Vitro Antimalarial Activity versus Plasmodium falciparum Malaria Parasites: Implications for the Molecular Mechanism of Action of the Artemisinins
    • O'Neill, P. M.; Rawe, S. L.; Borstnik, K.; Miller, A.; Ward, S. A.; Bray, P. G.; Davies, J.; Oh, C. H.; Posner, G. H. Enantiomeric 1,2,4-Trioxanes Display Equivalent in Vitro Antimalarial Activity versus Plasmodium falciparum Malaria Parasites: Implications for the Molecular Mechanism of Action of the Artemisinins. ChemBioChem 2005, 6, 2048-2054.
    • (2005) ChemBioChem , vol.6 , pp. 2048-2054
    • O'Neill, P.M.1    Rawe, S.L.2    Borstnik, K.3    Miller, A.4    Ward, S.A.5    Bray, P.G.6    Davies, J.7    Oh, C.H.8    Posner, G.H.9
  • 33
    • 42049102584 scopus 로고    scopus 로고
    • Creek, D. J.; Charman, W. N.; Chiu, F. C. K.; Prankerd, R. J.; Dong, Y.; Vennerstrom, J. L.; Charman, S. A. Relationship between Antimalarial Activity and Haem Alkylation for Spiroand Dispiro-1,2,4-trioxolane Antimalarial. Antimicrob. Agents Chemother. 2008, 52, 1291-1296.
    • Creek, D. J.; Charman, W. N.; Chiu, F. C. K.; Prankerd, R. J.; Dong, Y.; Vennerstrom, J. L.; Charman, S. A. Relationship between Antimalarial Activity and Haem Alkylation for Spiroand Dispiro-1,2,4-trioxolane Antimalarial. Antimicrob. Agents Chemother. 2008, 52, 1291-1296.
  • 38
    • 58249143778 scopus 로고    scopus 로고
    • Accumulation of Artemisinin Trioxane Derivatives Within Neutral Lipids of Plasmodium falciparum Malaria Parasites is Endoperoxide-dependent
    • Hartwig, C. L.; Rosenthal, A. S.; D'Angelo, J.; Griffin, C. E.; Posner, G. H.; Cooper, R. A. Accumulation of Artemisinin Trioxane Derivatives Within Neutral Lipids of Plasmodium falciparum Malaria Parasites is Endoperoxide-dependent. Biochem. Pharmacol. 2009, 77, 322-336.
    • (2009) Biochem. Pharmacol , vol.77 , pp. 322-336
    • Hartwig, C.L.1    Rosenthal, A.S.2    D'Angelo, J.3    Griffin, C.E.4    Posner, G.H.5    Cooper, R.A.6
  • 39
    • 74849108164 scopus 로고    scopus 로고
    • A Process for the Preparation of Known Antimalarials Spiro and Dispiro 1,2,4-Trioxolanes and Salts Thereof
    • PCT Int. Appl. WO 2007138435
    • Yadav, G. C.; Dorwal, H. N.; Valavala, S.; Sharma, V. K. A Process for the Preparation of Known Antimalarials Spiro and Dispiro 1,2,4-Trioxolanes and Salts Thereof. PCT Int. Appl. WO 2007138435 2007,.
    • (2007)
    • Yadav, G.C.1    Dorwal, H.N.2    Valavala, S.3    Sharma, V.K.4
  • 40
    • 33646123780 scopus 로고    scopus 로고
    • Seo, J. W.; Comninos, J. S.; Chi, D. Y.; Kim; Dong, W.; Carlson, K. E.; Katzenellenbogen, J. A. Fluorine-Substituted Cyclofenil Derivatives as Estrogen Receptor Ligands: Synthesis and Structure - Affinity Relationship Study of Potential Positron Emission Tomography Agents for Imaging Estrogen Receptors in Breast Cancer. J. Med. Chem. 2006, 49, 2496-2511.
    • Seo, J. W.; Comninos, J. S.; Chi, D. Y.; Kim; Dong, W.; Carlson, K. E.; Katzenellenbogen, J. A. Fluorine-Substituted Cyclofenil Derivatives as Estrogen Receptor Ligands: Synthesis and Structure - Affinity Relationship Study of Potential Positron Emission Tomography Agents for Imaging Estrogen Receptors in Breast Cancer. J. Med. Chem. 2006, 49, 2496-2511.
  • 41
    • 0001037197 scopus 로고
    • Synthesis of 1-Amino-1-(aminomethyl)cyclopropane and its Monobenzamides
    • Vergne, F.; Aitken, D. J.; Husson, H.-P. Synthesis of 1-Amino-1-(aminomethyl)cyclopropane and its Monobenzamides. J. Org. Chem. 1992, 57, 6071-6075.
    • (1992) J. Org. Chem , vol.57 , pp. 6071-6075
    • Vergne, F.1    Aitken, D.J.2    Husson, H.-P.3
  • 42
    • 0018606732 scopus 로고
    • Quantitative Assessment of Antimalarial Activity in Vitro by a Semiautomated Microdilution Technique
    • Desjardins, R. E.; Canfield, C. J.; Haynes, J. D.; Chulay, J. D. Quantitative Assessment of Antimalarial Activity in Vitro by a Semiautomated Microdilution Technique. Antimicrob. Agents Chemother. 1979, 16, 710-718.
    • (1979) Antimicrob. Agents Chemother , vol.16 , pp. 710-718
    • Desjardins, R.E.1    Canfield, C.J.2    Haynes, J.D.3    Chulay, J.D.4
  • 43
    • 0031018611 scopus 로고    scopus 로고
    • 2-Bis-(7-chloroquinolin-4-yl)cyclohexane-1,2-diamine: Comparison of Two Stereoisomers and Detailed Evaluation of the S,SEnantiomer, Ro 47-7737. Antimicrob.AgentsChemother. 1997, 41, 677-686.
    • 2-Bis-(7-chloroquinolin-4-yl)cyclohexane-1,2-diamine: Comparison of Two Stereoisomers and Detailed Evaluation of the S,SEnantiomer, Ro 47-7737. Antimicrob.AgentsChemother. 1997, 41, 677-686.


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