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Volumn 51, Issue 15, 2008, Pages 4660-4671

Design, synthesis, and biological evaluation of antiviral agents targeting flavivirus envelope proteins

Author keywords

[No Author keywords available]

Indexed keywords

2 ((2 (4 CHLOROPHENYL)THIAZOL 4 YL)METHYLTHIO)ANILINE; 2 (3 (4 (1 (2 CARBAMIMIDOYLHYDRAZONO) ETHYL) PHENYL) UREIDO) N (2,4 DICHLOROBENZYL) 4 METHYLTHIAZOLE 5 CARBOXAMIDE; 2 (3 (4 (1 (2 CARBAMOYLHYDRAZONO) ETHYL) UREIDO) N (2,4 DICHLOROBENZYL) 4 METHYLTHIAZOLE 5 CARBOXAMIDE; 2 (3 (4 ACETYLPHENYL) UREIDO) N (2,4 DICHLOROBENZYL) 4 METHYLTHIAZOLE 5 CARBOXAMIDE; 2 (3 (4 ACETYLPHENYL) UREIDO) N (3,4 DICHLOROBENZYL) 4 METHYLTHIAZOLE 5 CARBOXAMIDE; 2 (3,5 DIPHENYL 1H PYRAZOL 1 YL) 4 METHYLTHIAZOLE 5 CARBOXYLIC ACID; 2 (4 CHLORO PHENYL) 4 DIBROMOMETHYL THIAZOLE 5 CARBOXYLIC ACID METHYL ESTER; 2 (4 CHLORO PHENYL) 4 METHYL THIAZOLE 5 CARBOXYLIC ACID ADAMANTAN 1 YLMETHYL ESTER; 2 (4 CHLOROPHENYL) 4 METHYLTHIAZOLE; 2 (4 CHOROPHEYNL) 4 METHYL THIAZOLE 5 CARBOXYLIC ACID METHYL ESTER; 2 (BIS(4 ACETYLBENZYL)AMINO) 4 METHYLTHIAZOLE 5 CARBOXYLIC ACID; 2 (BIS(4 ACETYLBENZYL)AMINO) N (2,4 DICHLOROBENZYL) 4 METHYLTHIAZOLE 5 CARBOXAMIDE; 2 [3 (4 ACETYLPHENYL) UREIDO] 4 METHYLTHIAZOLE 5 CARBOXYLIC ACID; 2 CHLORO 3 OXO BUTYRIC ACID METHYL ESTER; 4 (CHLOROMETHYL) 2 (4 CHLOROPHENYL)THIAZOLE; ANTIVIRUS AGENT; ETHYL 2 (3,5 DIPHENYL 1H PYRAZOL 1 YL) 4 METHYLTHIAZOLE 5 CARBOXYLATE; METHYL 2 (3 (4 (1 (2 CARBAMIMIDOYLHYDRAZANO) ETHYL) PHENYL) UREIDO) 4 METHYLTHIAZOLE 5 CARBOXYLATE; METHYL 2 (3 (4 (1 (2 CARBAMOYLHYDRAZANO) ETHYL) PHENYL) UREIDO) 4 METHYLTHIAZOLE 5 CARBOXYLATE; METHYL 2 (3 (4 ACETYLPHENYL)UREIDO) 4 METHYLTHIAZOLE 5 CARBOXYLATE; METHYL 2 (BIS(4 ACETYLBENZYL)AMINO) 4 METHYLTHIAZOLE 5 CARBOXYLATE; METHYL 2 (N (4 ACETYLBENZYL)ACETAMIDO) 4 METHYLTHIAZOLE 5 CARBOXYLATE; METHYL 2 AMINO 4 METHYLTHIAZOLE 5 CARBOXYLATE; METHYL 2 BROMO 3 OXOBUTANOATE; N (3,4 DICHLOROBENZYL) 2 (3,5 DIPHENYL 1H PYRAZOL 1 YL) 4 METHYLTHIAZOLE 5 CARBOXAMIDE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; VIRUS ENVELOPE PROTEIN;

EID: 49449094472     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm800412d     Document Type: Article
Times cited : (96)

References (32)
  • 3
    • 33847671789 scopus 로고    scopus 로고
    • c-Src Protein Kinase Inhibitors Block Assembly and Maturation of Dengue Virus
    • Chu, J. J. H.; Yang, P. L. c-Src Protein Kinase Inhibitors Block Assembly and Maturation of Dengue Virus. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 3520-3525.
    • (2007) Proc. Natl. Acad. Sci. U.S.A , vol.104 , pp. 3520-3525
    • Chu, J.J.H.1    Yang, P.L.2
  • 5
    • 21644477919 scopus 로고    scopus 로고
    • Whitby, K.; Pierson, T. C.; Geiss, B.; Lane, K.; Engle, M.; Zhou, Y.; Doms, R. W.; Diamond, M. S. Castanospermine, a Potent Inhibitor of Dengue Virus Infection In Vitro and In Vivo. J. Virol. 2005, 79, 8698-8706.
    • Whitby, K.; Pierson, T. C.; Geiss, B.; Lane, K.; Engle, M.; Zhou, Y.; Doms, R. W.; Diamond, M. S. Castanospermine, a Potent Inhibitor of Dengue Virus Infection In Vitro and In Vivo. J. Virol. 2005, 79, 8698-8706.
  • 6
    • 2942700289 scopus 로고    scopus 로고
    • Action of Celgosivir (6 O-Butanoyl Castanospermine) Against the Pestivirus BVDV: Implications for the Treatment of Hepatitis C
    • Whitby, K.; Taylor, D.; Patel, D.; Ahmed, P.; Tyms, A. S. Action of Celgosivir (6 O-Butanoyl Castanospermine) Against the Pestivirus BVDV: Implications for the Treatment of Hepatitis C. Antiviral Chem. Chemother. 2004, 15, 141-151.
    • (2004) Antiviral Chem. Chemother , vol.15 , pp. 141-151
    • Whitby, K.1    Taylor, D.2    Patel, D.3    Ahmed, P.4    Tyms, A.S.5
  • 7
    • 15544387798 scopus 로고    scopus 로고
    • Use of RNA Interference to Prevent Lethal Murine West Nile Virus Infection
    • Bai, F. W.; Wang, T.; Pal, U.; Bao, F.; Gould, L. H.; Fikrig, E. Use of RNA Interference to Prevent Lethal Murine West Nile Virus Infection. J. Infect. Dis. 2005, 191, 1148-1154.
    • (2005) J. Infect. Dis , vol.191 , pp. 1148-1154
    • Bai, F.W.1    Wang, T.2    Pal, U.3    Bao, F.4    Gould, L.H.5    Fikrig, E.6
  • 8
    • 13744258758 scopus 로고    scopus 로고
    • The Predominant Mechanism by which Ribavirin Exerts Its Antiviral Activity In Vitro Against Faviviruses and Paramyxoviruses Is Mediated by Inhibition of IMP Dehydrogenase
    • Leyssen, P.; Balzarini, J.; De Clercq, E.; Neyts, J. The Predominant Mechanism by which Ribavirin Exerts Its Antiviral Activity In Vitro Against Faviviruses and Paramyxoviruses Is Mediated by Inhibition of IMP Dehydrogenase. J. Virol. 2005, 79, 1943-1947.
    • (2005) J. Virol , vol.79 , pp. 1943-1947
    • Leyssen, P.1    Balzarini, J.2    De Clercq, E.3    Neyts, J.4
  • 9
    • 4143116991 scopus 로고    scopus 로고
    • A Structural Basis for the Inhibition of the NS5 Dengue Virus mRNA 2′-O-Methyltransferase Domain by Ribavirin 5′-Triphosphate
    • Benarroch, D.; Egloff, M. P.; Mulard, L.; Guerreiro, C.; Romette, J. L.; Canard, B. A Structural Basis for the Inhibition of the NS5 Dengue Virus mRNA 2′-O-Methyltransferase Domain by Ribavirin 5′-Triphosphate. J. Biol. Chem. 2004, 279, 35638-35643.
    • (2004) J. Biol. Chem , vol.279 , pp. 35638-35643
    • Benarroch, D.1    Egloff, M.P.2    Mulard, L.3    Guerreiro, C.4    Romette, J.L.5    Canard, B.6
  • 10
    • 42049098403 scopus 로고    scopus 로고
    • Angusti, A.; Manfredini, S.; Durini, E.; Ciliberti, N.; Vertuani, S.; Solaroli, N.; Pricl, S.; Ferrone, M.; Fermeglia, M.; Loddo, R.; Secci, B.; Visioli, A.; Sanna, T.; Collu, G.; Pezzullo, M.; La.Colla, P. Design, Synthesis, and Anti Flaviviridae Activity of N(6)-5′,3′-O- and 5′,2′-O-Substituted Adenine Nucleoside Analogs. Chem. Pharm. Bull. 2008, 56, 423-432.
    • Angusti, A.; Manfredini, S.; Durini, E.; Ciliberti, N.; Vertuani, S.; Solaroli, N.; Pricl, S.; Ferrone, M.; Fermeglia, M.; Loddo, R.; Secci, B.; Visioli, A.; Sanna, T.; Collu, G.; Pezzullo, M.; La.Colla, P. Design, Synthesis, and Anti Flaviviridae Activity of N(6)-5′,3′-O- and 5′,2′-O-Substituted Adenine Nucleoside Analogs. Chem. Pharm. Bull. 2008, 56, 423-432.
  • 11
    • 33846781732 scopus 로고    scopus 로고
    • Bai, F. W.; Town, T.; Pradhan, D.; Cox, J.; Ashish; Ledizet, M.; Anderson, J. F.; Flavell, R. A.; Krueger, J. K.; Koski, R. A.; Fikrig, E. Antiviral Peptides Targeting the West Nile Virus Envelope Protein. J. Virol. 2007, 81, 2047-2055.
    • Bai, F. W.; Town, T.; Pradhan, D.; Cox, J.; Ashish; Ledizet, M.; Anderson, J. F.; Flavell, R. A.; Krueger, J. K.; Koski, R. A.; Fikrig, E. Antiviral Peptides Targeting the West Nile Virus Envelope Protein. J. Virol. 2007, 81, 2047-2055.
  • 12
    • 0034567567 scopus 로고    scopus 로고
    • Structures and Mechanism in Flavivirus Fusion
    • Heinz, F. X.; Allison, S. L. Structures and Mechanism in Flavivirus Fusion. Adv. Virus Res. 2000, 55, 231-269.
    • (2000) Adv. Virus Res , vol.55 , pp. 231-269
    • Heinz, F.X.1    Allison, S.L.2
  • 13
    • 0029014434 scopus 로고
    • The Envelope Glycoportein from Tick-borne Encephalitis Virus at 2 Å Resolution
    • Rey, F. A.; Heinz, F. X.; Mandl, C.; Kunz, C.; Harrison, S. C. The Envelope Glycoportein from Tick-borne Encephalitis Virus at 2 Å Resolution. Nature 1995, 375, 291-298.
    • (1995) Nature , vol.375 , pp. 291-298
    • Rey, F.A.1    Heinz, F.X.2    Mandl, C.3    Kunz, C.4    Harrison, S.C.5
  • 17
    • 0021931640 scopus 로고
    • Synthesis and Biological-Activity of 3′-Azido Substituted and 3′-Amino Substituted Nucleoside Analogs
    • Colla, L.; Herdewijn, P.; Declercq, E.; Balzarini, J.; Vanderhaeghe, H. Synthesis and Biological-Activity of 3′-Azido Substituted and 3′-Amino Substituted Nucleoside Analogs. Eur. J. Med. Chem. 1985, 20, 295-301.
    • (1985) Eur. J. Med. Chem , vol.20 , pp. 295-301
    • Colla, L.1    Herdewijn, P.2    Declercq, E.3    Balzarini, J.4    Vanderhaeghe, H.5
  • 18
    • 0025981170 scopus 로고
    • Nucleotide Changes Responsible for Loss of Neuroinvasiveness in Japanese Encephalitis-Virus Neutralization-Resistant Mutants
    • Cecilia, D.; Gould, E. A. Nucleotide Changes Responsible for Loss of Neuroinvasiveness in Japanese Encephalitis-Virus Neutralization-Resistant Mutants. Virology 1991, 181, 70-77.
    • (1991) Virology , vol.181 , pp. 70-77
    • Cecilia, D.1    Gould, E.A.2
  • 20
    • 0030738578 scopus 로고    scopus 로고
    • Changes in the Dengue Virus Major Envelope Protein on Passaging and their Localization on the Three-dimensional Structure of the Protein
    • Lee, E.; Weir, R. C.; Dalgarno, L. Changes in the Dengue Virus Major Envelope Protein on Passaging and their Localization on the Three-dimensional Structure of the Protein. Virology 1997, 232, 281-290.
    • (1997) Virology , vol.232 , pp. 281-290
    • Lee, E.1    Weir, R.C.2    Dalgarno, L.3
  • 21
    • 0035864283 scopus 로고    scopus 로고
    • Epitopes on the Dengue 1 Virus Envelope Protein Recognized by Neutralizing IgM Monoclonal Antibodies
    • Beasley, D. W. C.; Aaskov, J. G. Epitopes on the Dengue 1 Virus Envelope Protein Recognized by Neutralizing IgM Monoclonal Antibodies. Virology 2001, 279, 447-458.
    • (2001) Virology , vol.279 , pp. 447-458
    • Beasley, D.W.C.1    Aaskov, J.G.2
  • 22
    • 0034909241 scopus 로고    scopus 로고
    • Attenuation of Murray Valley Encephalitis Virus by Site-directed Mutagenesis of the Hinge and Putative Receptor-binding Regions of the Envelope Protein
    • Hurrelbrink, R. J.; McMinn, P. C. Attenuation of Murray Valley Encephalitis Virus by Site-directed Mutagenesis of the Hinge and Putative Receptor-binding Regions of the Envelope Protein. J. Virol. 2001, 75, 7692-7702.
    • (2001) J. Virol , vol.75 , pp. 7692-7702
    • Hurrelbrink, R.J.1    McMinn, P.C.2
  • 23
    • 0036148484 scopus 로고    scopus 로고
    • Single Mutation in the Flavivirus Envelope Protein Hinge Region Increases Neurovirulence for Mice and Monkeys but Decreases Viscerotropism for Monkeys: Relevance to Development and Safety Testing of Live, Attenuated Vaccines
    • Monath, T. P.; Arroyo, J.; Levenbook, I.; Zhang, Z. X.; Catalan, J.; Draper, K.; Guirakhoo, F. Single Mutation in the Flavivirus Envelope Protein Hinge Region Increases Neurovirulence for Mice and Monkeys but Decreases Viscerotropism for Monkeys: Relevance to Development and Safety Testing of Live, Attenuated Vaccines. J. Virol. 2002, 76, 1932-1943.
    • (2002) J. Virol , vol.76 , pp. 1932-1943
    • Monath, T.P.1    Arroyo, J.2    Levenbook, I.3    Zhang, Z.X.4    Catalan, J.5    Draper, K.6    Guirakhoo, F.7
  • 24
    • 0037154810 scopus 로고    scopus 로고
    • Synthesis of 2-Oxazolone-4-carboxylates from 3-Nosyloxy- and 3-Bromo-2-ketoesters
    • Okonya, J. F.; Hoffman, R. V.; Johnson, M. C. Synthesis of 2-Oxazolone-4-carboxylates from 3-Nosyloxy- and 3-Bromo-2-ketoesters. J. Org. Chem. 2002, 67, 1102-1108.
    • (2002) J. Org. Chem , vol.67 , pp. 1102-1108
    • Okonya, J.F.1    Hoffman, R.V.2    Johnson, M.C.3
  • 25
    • 11244333701 scopus 로고
    • Thiazole Analogs of Pyridoxine
    • Conover, L. H.; Tarbell, D. S. Thiazole Analogs of Pyridoxine. J. Am. Chem. Soc. 1950, 72, 5221-5225.
    • (1950) J. Am. Chem. Soc , vol.72 , pp. 5221-5225
    • Conover, L.H.1    Tarbell, D.S.2
  • 26
    • 0017826147 scopus 로고
    • Guanylhydrazones with Potential Anti-Leukemic Activity 0.2. Synthesis and Structure-Activity Relationships of Analogs of 4,4′-Diacetyl-N,N′-Diphenylurea Bis(Guanylhydrazone)
    • Korytnyk, W.; Angelino, N.; Dave, C.; Caballes, L. Guanylhydrazones with Potential Anti-Leukemic Activity 0.2. Synthesis and Structure-Activity Relationships of Analogs of 4,4′-Diacetyl-N,N′-Diphenylurea Bis(Guanylhydrazone). J. Med. Chem. 1978, 21, 507-513.
    • (1978) J. Med. Chem , vol.21 , pp. 507-513
    • Korytnyk, W.1    Angelino, N.2    Dave, C.3    Caballes, L.4
  • 28
    • 0014540588 scopus 로고    scopus 로고
    • Brown, K.; Newberry, R. A. A Novel Synthesis of 4-Hydroxymethyl-2- Phenylthiazole Involving an Epoxy-2-Thiazoline Intermediate. Tetrahedron Lett. 1969, 2797-2708.
    • Brown, K.; Newberry, R. A. A Novel Synthesis of 4-Hydroxymethyl-2- Phenylthiazole Involving an Epoxy-2-Thiazoline Intermediate. Tetrahedron Lett. 1969, 2797-2708.
  • 29
    • 0034605131 scopus 로고    scopus 로고
    • Phenyloxazoles and phenylthiazoles as benzamide bioisosteres: Synthesis and dopamine receptor binding profiles
    • Einsiedel, J.; Thomas, C.; Hubner, H.; Gmeiner, P. Phenyloxazoles and phenylthiazoles as benzamide bioisosteres: Synthesis and dopamine receptor binding profiles. Bioorg. Med. Chem. Lett. 2000, 10, 2041-2044.
    • (2000) Bioorg. Med. Chem. Lett , vol.10 , pp. 2041-2044
    • Einsiedel, J.1    Thomas, C.2    Hubner, H.3    Gmeiner, P.4
  • 30
    • 20444398250 scopus 로고    scopus 로고
    • De Kimpe, N.; De Cock, W.; Schamp, N. A. A Convenient Synthesis of 1-Chloro-2-alkanones. Synthesis 1987, 2, 188-190.
    • De Kimpe, N.; De Cock, W.; Schamp, N. A. A Convenient Synthesis of 1-Chloro-2-alkanones. Synthesis 1987, 2, 188-190.
  • 31
    • 0019832137 scopus 로고
    • Unfused Heterobicycles as Amplifiers of Phleomycin. 3. Thiazolylpyridines and Bipyrimidines with Strongly Basic Side Chains
    • Brown, D. J.; Buttler, B. B.; Cowden, W. B.; Grigg, G. W.; Kavulak, D.; Podger, D. M. Unfused Heterobicycles as Amplifiers of Phleomycin. 3. Thiazolylpyridines and Bipyrimidines with Strongly Basic Side Chains. Aust. J. Chem. 1981, 34, 2423-2429.
    • (1981) Aust. J. Chem , vol.34 , pp. 2423-2429
    • Brown, D.J.1    Buttler, B.B.2    Cowden, W.B.3    Grigg, G.W.4    Kavulak, D.5    Podger, D.M.6
  • 32
    • 11344251060 scopus 로고    scopus 로고
    • Construction and Applications of Yellow Fever Virus Replicons
    • Jones, C. T.; Patkar, C. G.; Kuhn, R. J. Construction and Applications of Yellow Fever Virus Replicons. Virology 2005, 331, 247-259.
    • (2005) Virology , vol.331 , pp. 247-259
    • Jones, C.T.1    Patkar, C.G.2    Kuhn, R.J.3


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