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Volumn 24, Issue 10-12, 2005, Pages 1417-1437

Design, synthesis, and antiviral evaluation of some polyhalogenated indole C-nucleosides

Author keywords

Antiviral; C Nucleoside; Human cytomegalovirus (HCMV); Indole nucleoside; Nucleoside analog; TCRB

Indexed keywords

1 ACETYL 3 (BETA DEXTRO RIBOFURANOSYL) 2,5,6 TRICHLOROINDOLE; 1 METHYL 3 (BETA DEXTRO RIBOFURANOSYL) 2,5,6 TRICHLOROINDOLE; 2 ACETYLPYRIDINE THIOSEMICARBAZONE; 2 BENZYLTHIO 5,6 DICHLORO 3 (BETA DEXTRO RIBOFURANOSYL)INDOLE; 2 BROMO 5,6 DICHLORO 1 (BETA DEXTRO RIBOFURANOSYL)BENZIMIDAZOLE; 2,5,6 TRICHLORO 1 (BETA DEXTRO RIBOFURANOSYL)BENZIMIDAZOLE; 3 (BETA DEXTRO RIBOFURANOSYL) 2,5,6 TRICHLOROINDOLE; ACICLOVIR; BENZIMIDAZOLE DERIVATIVE; C NUCLEOSIDE; GANCICLOVIR; INDOLE DERIVATIVE; LEWIS ACID; UNCLASSIFIED DRUG;

EID: 29244483434     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770500265646     Document Type: Article
Times cited : (23)

References (29)
  • 1
    • 0028853743 scopus 로고
    • Design, synthesis, and antiviral activity of certain 2,5,6-trihalo-1- (β-D-ribofuranosyl)benzimidazoles
    • Townsend, L.B.; Devivar, R.V.; Turk, S.R.; Nassiri, M.R.; Drach, J.C. Design, synthesis, and antiviral activity of certain 2,5,6-trihalo-1-(β-D- ribofuranosyl)benzimidazoles. J. Med. Chem. 1995, 38, 4098-4105.
    • (1995) J. Med. Chem. , vol.38 , pp. 4098-4105
    • Townsend, L.B.1    Devivar, R.V.2    Turk, S.R.3    Nassiri, M.R.4    Drach, J.C.5
  • 2
    • 0028129709 scopus 로고
    • Benzimidazole ribonucleosides: Design, synthesis, and antiviral activity of certain 2-(alkylthio)- and 2-(benzylthio)-5,6-dichloro-1-(β-D- ribofuranosyl)benzimidazoles
    • Devivar, R.V.; Kawashima, E.; Revankar, G.R.; Breitenbach, J.M.; Kreske, E.D.; Drach, J.C.; Townsend, L.B. Benzimidazole ribonucleosides: Design, synthesis, and antiviral activity of certain 2-(alkylthio)- and 2-(benzylthio)-5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazoles. J. Med. Chem. 1994, 37, 2942-2949.
    • (1994) J. Med. Chem. , vol.37 , pp. 2942-2949
    • Devivar, R.V.1    Kawashima, E.2    Revankar, G.R.3    Breitenbach, J.M.4    Kreske, E.D.5    Drach, J.C.6    Townsend, L.B.7
  • 3
    • 0000093809 scopus 로고
    • The disposition in rats and monkeys of 2-bromo-5,6-dichloro-1-(β-D- ribofuranosyl)benzimidazole (BDCRB) and its 2,5,6-trichloro congener
    • Good, S.S.; Owens, B.S.; Townsend, L.B.; Drach, J.C. The disposition in rats and monkeys of 2-bromo-5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole (BDCRB) and its 2,5,6-trichloro congener. Antiviral Res. 1994, 23(S), 103.
    • (1994) Antiviral Res. , vol.23 , Issue.S , pp. 103
    • Good, S.S.1    Owens, B.S.2    Townsend, L.B.3    Drach, J.C.4
  • 4
    • 0033937315 scopus 로고    scopus 로고
    • Synthesis and antiviral evaluation of trisubstituted indole N-nucleosides as analogues of 2,5,6-trichloro-1-(β-D-ribofuranosyl)benzimidazole (TCRB)
    • Chen, J.J.; Wei, Y.; Drach, J.C.; Townsend, L.B. Synthesis and antiviral evaluation of trisubstituted indole N-nucleosides as analogues of 2,5,6-trichloro-1-(β-D-ribofuranosyl)benzimidazole (TCRB). J. Med. Chem. 2000, 43, 2449-2456.
    • (2000) J. Med. Chem. , vol.43 , pp. 2449-2456
    • Chen, J.J.1    Wei, Y.2    Drach, J.C.3    Townsend, L.B.4
  • 5
    • 7444233117 scopus 로고    scopus 로고
    • Design, synthesis, and antiviral activity of certain 3-substituted 2,5,6-trichloroindole nucleosides
    • Williams, J.D.; Chen, J.J.; Drach, J.C.; Townsend, L.B. Design, synthesis, and antiviral activity of certain 3-substituted 2,5,6-trichloroindole nucleosides. J. Med. Chem. 2004, 47, 5753-5765.
    • (2004) J. Med. Chem. , vol.47 , pp. 5753-5765
    • Williams, J.D.1    Chen, J.J.2    Drach, J.C.3    Townsend, L.B.4
  • 6
    • 7444229249 scopus 로고    scopus 로고
    • Synthesis and antiviral activity of some 3-formyl- and 3-cyano-2,5,6-trichloroindole nucleoside derivatives
    • Williams, J.D.; Chen, J.J.; Drach, J.C.; Townsend, L.B. Synthesis and antiviral activity of some 3-formyl- and 3-cyano-2,5,6-trichloroindole nucleoside derivatives. J. Med. Chem. 2004, 47, 5766-5772.
    • (2004) J. Med. Chem. , vol.47 , pp. 5766-5772
    • Williams, J.D.1    Chen, J.J.2    Drach, J.C.3    Townsend, L.B.4
  • 7
    • 7444238718 scopus 로고    scopus 로고
    • Synthesis, antiviral activity, and mode of action of some 3-substituted 2,5,6-trichloroindole 2′- and 5′-deoxyribonucleosides
    • Williams, J.D.; Ptak, R.G.; Drach, J.C.; Townsend, L.B. Synthesis, antiviral activity, and mode of action of some 3-substituted 2,5,6-trichloroindole 2′- and 5′-deoxyribonucleosides. J. Med. Chem. 2004, 47, 5773-7582.
    • (2004) J. Med. Chem. , vol.47 , pp. 5773-7582
    • Williams, J.D.1    Ptak, R.G.2    Drach, J.C.3    Townsend, L.B.4
  • 8
    • 29244473579 scopus 로고    scopus 로고
    • Synthesis and antiviral activity of some 2-substituted 3-formyl- and 3-cyano-5,6-dichloroindole nucleosides
    • In press
    • Williams, J.D.; Drach, J.C.; Townsend, L.B. Synthesis and antiviral activity of some 2-substituted 3-formyl- and 3-cyano-5,6-dichloroindole nucleosides. Nucleosides, Nucleotides, and Nucleic Acids. In press.
    • Nucleosides, Nucleotides, and Nucleic Acids
    • Williams, J.D.1    Drach, J.C.2    Townsend, L.B.3
  • 9
    • 0029835371 scopus 로고    scopus 로고
    • Synthesis and antiviral evaluation of certain disubstituted benzimidazole ribonucleosides
    • Zou, R.; Ayres, K.R.; Drach, J.C.; Townsend, L.B. Synthesis and antiviral evaluation of certain disubstituted benzimidazole ribonucleosides. J. Med. Chem. 1996, 39, 3477-3482.
    • (1996) J. Med. Chem. , vol.39 , pp. 3477-3482
    • Zou, R.1    Ayres, K.R.2    Drach, J.C.3    Townsend, L.B.4
  • 10
    • 0031058374 scopus 로고    scopus 로고
    • Design, synthesis, and antiviral evaluation of 2-chloro-5,6-dihalo-1- β-D-ribofuranosylbenzimidazoles as potential agents for human cytomegalovirus infections
    • Zou, R.; Drach, J.C.; Townsend, L.B. Design, synthesis, and antiviral evaluation of 2-chloro-5,6-dihalo-1-β-D-ribofuranosylbenzimidazoles as potential agents for human cytomegalovirus infections. J. Med. Chem. 1997, 40, 811-818.
    • (1997) J. Med. Chem. , vol.40 , pp. 811-818
    • Zou, R.1    Drach, J.C.2    Townsend, L.B.3
  • 11
    • 0031048289 scopus 로고    scopus 로고
    • Design, synthesis, and antiviral evaluation of 2-substituted 4,5-dichloro- and 4,6-dichloro-1-β-D-ribofuranosylbenzimidazoles as potential agents for human cytomegalovirus infections
    • Zou, R.; Drach, J.C.; Townsend, L.B. Design, synthesis, and antiviral evaluation of 2-substituted 4,5-dichloro- and 4,6-dichloro-1-β-D- ribofuranosylbenzimidazoles as potential agents for human cytomegalovirus infections. J. Med. Chem. 1997, 40, 802-810.
    • (1997) J. Med. Chem. , vol.40 , pp. 802-810
    • Zou, R.1    Drach, J.C.2    Townsend, L.B.3
  • 12
    • 0034110178 scopus 로고    scopus 로고
    • Design, synthesis, and antiviral evaluation of 2-deoxy-D-ribosides of substituted benzimidazoles as potential agents for human cytomegalovirus infections
    • Zou, R.; Kawashima, E.; Freeman, G.A.; Koszalka, G.W.; Drach, J.C.; Townsend, L.B. Design, synthesis, and antiviral evaluation of 2-deoxy-D-ribosides of substituted benzimidazoles as potential agents for human cytomegalovirus infections. Nucleosides Nucleotides Nucleic Acids 2000, 19, 125-154.
    • (2000) Nucleosides Nucleotides Nucleic Acids , vol.19 , pp. 125-154
    • Zou, R.1    Kawashima, E.2    Freeman, G.A.3    Koszalka, G.W.4    Drach, J.C.5    Townsend, L.B.6
  • 13
    • 0031052117 scopus 로고    scopus 로고
    • Synthesis and antiviral activity of certain 5′-modified analogs of 2,5,6-trichloro-1-(β-D-ribofuranosyl)benziminazole
    • Gudmundsson, K.S.; Drach, J.C.; Wotring, L.L.; Townsend, L.B. Synthesis and antiviral activity of certain 5′-modified analogs of 2,5,6-trichloro-1-(β-D-ribofuranosyl)benziminazole. J. Med. Chem. 1997, 40, 785-793.
    • (1997) J. Med. Chem. , vol.40 , pp. 785-793
    • Gudmundsson, K.S.1    Drach, J.C.2    Wotring, L.L.3    Townsend, L.B.4
  • 15
    • 0025826240 scopus 로고
    • C-Heteroarylation of sugars by indolylbromomagnesium salts. Synthesis of 3-(alditol-1-yl)indoles and their cyclization to indole C-nucleoside analogs
    • Cornia, M.; Casiraghi, G.; Zetta, L. C-Heteroarylation of sugars by indolylbromomagnesium salts. Synthesis of 3-(alditol-1-yl)indoles and their cyclization to indole C-nucleoside analogs. J. Org. Chem. 1991, 56, 5466-5468.
    • (1991) J. Org. Chem. , vol.56 , pp. 5466-5468
    • Cornia, M.1    Casiraghi, G.2    Zetta, L.3
  • 16
    • 29244457177 scopus 로고
    • Un Nouveau systeme pseudoazulenique
    • Bourdais, J. Un Nouveau systeme pseudoazulenique. Tetrahedron Lett. 1970, 2895-2898.
    • (1970) Tetrahedron Lett. , pp. 2895-2898
    • Bourdais, J.1
  • 18
    • 0005175546 scopus 로고
    • The Knoevenagal-Doebner reaction on 2,3-isopropylidene derivatives of D-ribo- and D-manno-furanose
    • Herrera, F.J.L.; Gonzalez, M.S.P. The Knoevenagal-Doebner reaction on 2,3-isopropylidene derivatives of D-ribo- and D-manno-furanose. Carbohydr. Res. 1986, 152, 283-291.
    • (1986) Carbohydr. Res. , vol.152 , pp. 283-291
    • Herrera, F.J.L.1    Gonzalez, M.S.P.2
  • 20
    • 0010683368 scopus 로고
    • A comparison of the Wittig and Knoevenagel-Doebner reactions for the chain extension of aldoses
    • Collins, P.M.; Overend, W.G.; Shing, T.S. A comparison of the Wittig and Knoevenagel-Doebner reactions for the chain extension of aldoses. J. Chem. Soc., Chem. Commun. 1982, 297-298.
    • (1982) J. Chem. Soc., Chem. Commun. , pp. 297-298
    • Collins, P.M.1    Overend, W.G.2    Shing, T.S.3
  • 23
    • 0002500874 scopus 로고
    • A convenient, one-step, high-yield replacement of an anomeric hydroxyl group by a fluorine atom using DAST. Preparation of glycosyl fluorides
    • Posner, G.H.; Haines, S.R. A convenient, one-step, high-yield replacement of an anomeric hydroxyl group by a fluorine atom using DAST. Preparation of glycosyl fluorides. Tetrahedron Lett. 1985, 26, 5-8.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 5-8
    • Posner, G.H.1    Haines, S.R.2
  • 25
    • 0017073707 scopus 로고
    • Antiviral activity of arabinofuranosyladenosine and arabinofuranosylhypoxanthine in herpes simplex virus-infected KB cells
    • Shipman, C., Jr.; Smith, S.H.; Carlson, R.H.; Drach, J.C. Antiviral activity of arabinofuranosyladenosine and arabinofuranosylhypoxanthine in herpes simplex virus-infected KB cells. Antimicrob. Agents Chemother. 1976, 9, 120-127.
    • (1976) Antimicrob. Agents Chemother. , vol.9 , pp. 120-127
    • Shipman Jr., C.1    Smith, S.H.2    Carlson, R.H.3    Drach, J.C.4
  • 28
    • 0024993530 scopus 로고
    • A three dimensional model to analyze drug-drug interactions
    • Prichard, M.N.; Shipman, C., Jr. A three dimensional model to analyze drug-drug interactions. Antiviral Res. 1990, 14, 181-206.
    • (1990) Antiviral Res. , vol.14 , pp. 181-206
    • Prichard, M.N.1    Shipman Jr., C.2
  • 29
    • 0025756141 scopus 로고
    • Three-dimensional analysis of synergistic cytotoxicity of ganciclovir and zidovudine
    • Prichard, M.N.; Prichard, L.E.; Baguley, W.A.; Nassiri, R.; Shipman, C., Jr. Three-dimensional analysis of synergistic cytotoxicity of ganciclovir and zidovudine. Antiviral Res. 1991, 35, 1060-1065.
    • (1991) Antiviral Res. , vol.35 , pp. 1060-1065
    • Prichard, M.N.1    Prichard, L.E.2    Baguley, W.A.3    Nassiri, R.4    Shipman Jr., C.5


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