메뉴 건너뛰기




Volumn 41, Issue 8, 1998, Pages 1242-1251

Design, synthesis, and antiviral activity of α-nucleosides: D- and L- isomers of lyxofuranosyl- and (5-deoxylyxofuranosyl)benzimidazoles

Author keywords

[No Author keywords available]

Indexed keywords

(5 DEOXYLYXOFURANOSYL)BENZIMIDAZOLE DERIVATIVE; ANTIVIRUS AGENT; BENZIMIDAVIR; FOSCARNET; GANCICLOVIR; LYXOFURANOSYL BENZIMIDAZOLE DERIVATIVE; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032499278     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970545c     Document Type: Article
Times cited : (238)

References (47)
  • 1
    • 0001947969 scopus 로고
    • Cytomegalovirus
    • Roizman, B., Whitley, R. J., Lopez, C., Eds.; Raven Press: New York
    • Alford, C. A.; Britt, W. J. Cytomegalovirus. In The Human Herpesviruses. Roizman, B., Whitley, R. J., Lopez, C., Eds.; Raven Press: New York, 1993; pp 227-255.
    • (1993) The Human Herpesviruses , pp. 227-255
    • Alford, C.A.1    Britt, W.J.2
  • 2
    • 0025146372 scopus 로고
    • Congenital and Perinatal Cytomegalovirus Infections in Bone Marrow Transplants
    • Alford, C. A.; Stagno, S.; Pass, R. F.; Brit, W. J. Congenital and Perinatal Cytomegalovirus Infections in Bone Marrow Transplants. Rev. Infect. Dis. 1990, 12, s793-s804.
    • (1990) Rev. Infect. Dis. , vol.12
    • Alford, C.A.1    Stagno, S.2    Pass, R.F.3    Brit, W.J.4
  • 3
    • 0026479981 scopus 로고
    • Incidence and Natural History of Cytomegalovirus Disease in Patients with Advanced Immunodeficiency Virus Disease Treated with Zidovudine
    • Gallant, J. E.; Moore, R. D.; Richman, D. D.; Keruly, J.; Chaisson, R. E. Incidence and Natural History of Cytomegalovirus Disease in Patients with Advanced Immunodeficiency Virus Disease Treated with Zidovudine. J. Infect. Dis. 1992, 166, 1223-1227.
    • (1992) J. Infect. Dis. , vol.166 , pp. 1223-1227
    • Gallant, J.E.1    Moore, R.D.2    Richman, D.D.3    Keruly, J.4    Chaisson, R.E.5
  • 5
    • 0026085287 scopus 로고
    • Foscarnet. A Review of its Antiviral Activity, Pharmacokinetic Properties and Therapeutic Use in Immunocompromised Patients with Cytomegalovirus Retinitis
    • Chrisp, P.; Clissold, S. P. Foscarnet. A Review of its Antiviral Activity, Pharmacokinetic Properties and Therapeutic Use in Immunocompromised Patients with Cytomegalovirus Retinitis. Drugs 1991, 41, 104-129.
    • (1991) Drugs , vol.41 , pp. 104-129
    • Chrisp, P.1    Clissold, S.P.2
  • 8
    • 0028156908 scopus 로고
    • "The End of Innocence" Revisited: Resistance of Herpesviruses to Antiviral Drugs
    • Field, A. K.; Biron, K. K. "The End of Innocence" Revisited: Resistance of Herpesviruses to Antiviral Drugs. Clin. Microbiol. Rev. 1994, 7, 1-13.
    • (1994) Clin. Microbiol. Rev. , vol.7 , pp. 1-13
    • Field, A.K.1    Biron, K.K.2
  • 9
    • 0011168555 scopus 로고
    • Inhibition of Influenza Virus Multiplication by N.-Glycosides of Benzimidazoles
    • Tamm, I.; Folkers, K.; Shunk, C. H.; Horsfall, F. L., Jr. Inhibition of Influenza Virus Multiplication by N.-Glycosides of Benzimidazoles. J. Exp. Med. 1954, 99, 227-250.
    • (1954) J. Exp. Med. , vol.99 , pp. 227-250
    • Tamm, I.1    Folkers, K.2    Shunk, C.H.3    Horsfall Jr., F.L.4
  • 10
    • 0014038835 scopus 로고
    • The Effects of Substituted Benzimidazoles on the Growth of Viruses and the Nucleic Acid Metabolism of Host Cells
    • (a) Bucknall, R. A. The Effects of Substituted Benzimidazoles on the Growth of Viruses and the Nucleic Acid Metabolism of Host Cells. J. Gen. Virol. 1967, 7, 89-99.
    • (1967) J. Gen. Virol. , vol.7 , pp. 89-99
    • Bucknall, R.A.1
  • 11
    • 0017915202 scopus 로고
    • Halobenzimidazole Ribosides and RNA Synthesis of Cells and Viruses
    • (b) Tamm, I.; Sehgal, P. B. Halobenzimidazole Ribosides and RNA Synthesis of Cells and Viruses. Adv. Virus Res. 1978, 22, 187-258.
    • (1978) Adv. Virus Res. , vol.22 , pp. 187-258
    • Tamm, I.1    Sehgal, P.B.2
  • 12
    • 0014803750 scopus 로고
    • Benzimidazole Nucleosides, Nucleotides, and Related Derivatives
    • Townsend, L. B.; Revankar, G. R. Benzimidazole Nucleosides, Nucleotides, and Related Derivatives. Chem. Rev. 1970, 70, 389-438.
    • (1970) Chem. Rev. , vol.70 , pp. 389-438
    • Townsend, L.B.1    Revankar, G.R.2
  • 13
    • 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. T.; 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.T.3    Nassiri, M.R.4    Drach, J.C.5
  • 14
    • 0029835371 scopus 로고    scopus 로고
    • Synthesis and Antiviral Activity of Certain Disubstituted Benzimidazole Ribonucleotides
    • Zou, R.; Ayres, K. R.; Drach, J. C.; Townsend, L. B. Synthesis and Antiviral Activity of Certain Disubstituted Benzimidazole Ribonucleotides. 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
  • 15
    • 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
  • 16
    • 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
  • 17
    • 0028129709 scopus 로고
    • Benzimidazole Ribonucleosides: Design, Synthesis, and Antiviral Activity of Certain 2-(Alkylthio)- and 2-(Benzylthio)-5,6-dichloro-1-β-D-ribofuranosylbenzimidazoles
    • 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, 2942-2948.
    • (1994) J. Med. Chem. , vol.37 , pp. 2942-2948
    • 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
  • 18
    • 0030067363 scopus 로고    scopus 로고
    • Structure-Activity Relationship among 2-Substituted 5,6-Dichloro-, 4,6-Dichloro-, and 4,5-Dichloro-1-[(2-hydroxyethoxy)methyl]- and -1-[(1,3-dihydroxy-2-propoxy)methyl]benzimidazoles
    • Saluja, S.; Zou, R.; Drach, J. C.; Townsend, L. B. Structure-Activity Relationship among 2-Substituted 5,6-Dichloro-, 4,6-Dichloro-, and 4,5-Dichloro-1-[(2-hydroxyethoxy)methyl]- and -1-[(1,3-dihydroxy-2-propoxy)methyl]benzimidazoles. J. Med. Chem. 1996, 39, 881-891.
    • (1996) J. Med. Chem. , vol.39 , pp. 881-891
    • Saluja, S.1    Zou, R.2    Drach, J.C.3    Townsend, L.B.4
  • 19
    • 0031052117 scopus 로고    scopus 로고
    • Synthesis and Antiviral Activity of Certain 5′-Modified Analogues of 2,5,6-Trichloro-1-(β-D-ribofuranosyl)benzimidazole
    • Gudmundsson, K. S.; Drach, J. C.; Wotring, L. L.; Townsend, L. B. Synthesis and Antiviral Activity of Certain 5′-Modified Analogues of 2,5,6-Trichloro-1-(β-D-ribofuranosyl)benzimidazole. 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
  • 23
    • 84982068675 scopus 로고
    • Nucleoside Synthesis with Trimethylsilyl Triflate and Perchlorate as Catalysts
    • Vorbrüggen, H.; Krolikiewicz, K.; Bennua, B. Nucleoside Synthesis with Trimethylsilyl Triflate and Perchlorate as Catalysts. Chem. Ber. 1981, 114, 1234-1255.
    • (1981) Chem. Ber. , vol.114 , pp. 1234-1255
    • Vorbrüggen, H.1    Krolikiewicz, K.2    Bennua, B.3
  • 24
    • 0001545332 scopus 로고
    • Puromycin Synthetic Studies. V. 6-Dimethylamino-9-(2′-acetylamino-β-D-glucopyranosyl)purine
    • Baker, B. R.; Joseph, J. P.; Schaub, R. E.; Williams, J. H. Puromycin Synthetic Studies. V. 6-Dimethylamino-9-(2′-acetylamino-β-D-glucopyranosyl)purine. J. Org. Chem. 1954, 19, 1786-1792.
    • (1954) J. Org. Chem. , vol.19 , pp. 1786-1792
    • Baker, B.R.1    Joseph, J.P.2    Schaub, R.E.3    Williams, J.H.4
  • 25
    • 0002269211 scopus 로고
    • An Improved Preparation of 1,2,3,5-Tetra-O-acetyl-β-D-ribofuranose
    • Guthrie, R. D.; Smith, S. C. An Improved Preparation of 1,2,3,5-Tetra-O-acetyl-β-D-ribofuranose. Chem. Ind. 1968, 547-548.
    • (1968) Chem. Ind. , pp. 547-548
    • Guthrie, R.D.1    Smith, S.C.2
  • 26
    • 0343086628 scopus 로고
    • 2,5,6-Trichlorobenzimidazole
    • Part 4; Townsend, L. B., Tipson, R. S., Eds.; John Wiley and Sons: New York
    • Kawashima, E.; Gupta, P. K.; Devivar, R. V.; Townsend, L. B. 2,5,6-Trichlorobenzimidazole. In Nucleic Acid Chemistry, Part 4; Townsend, L. B., Tipson, R. S., Eds.; John Wiley and Sons: New York, 1991; pp 24-26.
    • (1991) Nucleic Acid Chemistry , pp. 24-26
    • Kawashima, E.1    Gupta, P.K.2    Devivar, R.V.3
  • 27
    • 84982058693 scopus 로고
    • On the Mechanism of Nucleoside Synthesis
    • Vorbrüggen, H.; Hofle, G. On the Mechanism of Nucleoside Synthesis. Chem. Ber. 1981, 114, 1256-1268.
    • (1981) Chem. Ber. , vol.114 , pp. 1256-1268
    • Vorbrüggen, H.1    Hofle, G.2
  • 28
    • 6444220423 scopus 로고
    • Nucleophilic Substitution Reaction of 2-Chlorobenzimidazoles. Part 1. Formation of Benzimidazolin-2-ones and 2-Alkoxybenzimidazoles
    • Harrison, D.; Ralph, J. T. Nucleophilic Substitution Reaction of 2-Chlorobenzimidazoles. Part 1. Formation of Benzimidazolin-2-ones and 2-Alkoxybenzimidazoles. J. Chem. Soc. 1965, 236-239.
    • (1965) J. Chem. Soc. , pp. 236-239
    • Harrison, D.1    Ralph, J.T.2
  • 29
    • 0011908120 scopus 로고
    • The Preparation of L-Lyxuronic acid, L-Lyxose, and 5-Deoxy-L-lyxose
    • Hulyalkar, R. K; Perry, M. B. The Preparation of L-Lyxuronic acid, L-Lyxose, and 5-Deoxy-L-lyxose. Can. J. Chem. 1965, 43, 3241-3246.
    • (1965) Can. J. Chem. , vol.43 , pp. 3241-3246
    • Hulyalkar, R.K.1    Perry, M.B.2
  • 30
    • 0017457614 scopus 로고
    • Enantiomeric Forms of 9-(5-Deoxy-β-erythro-pent-4-enofuranosyl)adenine and a New Preparation of 5-Deoxy-D-lyxose
    • Lerner, L. M. Enantiomeric Forms of 9-(5-Deoxy-β-erythro-pent-4-enofuranosyl)adenine and a New Preparation of 5-Deoxy-D-lyxose. Carbohydr. Res. 1977, 53, 177-185.
    • (1977) Carbohydr. Res. , vol.53 , pp. 177-185
    • Lerner, L.M.1
  • 31
    • 0023655220 scopus 로고
    • 13C]-Enriched 5-Deoxypentoses and 5-O-Methylpentoses
    • 13C]-Enriched 5-Deoxypentoses and 5-O-Methylpentoses. Carbohydr. Res. 1987, 163, 169-188.
    • (1987) Carbohydr. Res. , vol.163 , pp. 169-188
    • Snyder, J.R.1    Serianni, A.S.2
  • 32
    • 0024301079 scopus 로고
    • Furanose Ring Anomerization: A Kinetic Study of 5-Deoxypentoses and 5-O-Methylpentoses
    • Snyder, J. S.; Serianni, A. S. Furanose Ring Anomerization: A Kinetic Study of 5-Deoxypentoses and 5-O-Methylpentoses. Carbohydr. Res. 1988, 184, 13-25.
    • (1988) Carbohydr. Res. , vol.184 , pp. 13-25
    • Snyder, J.S.1    Serianni, A.S.2
  • 34
    • 0025696516 scopus 로고
    • 1,3,5-Tri-O-acetyl-2-deoxy-α,β-D-erythro-pentofuranose from 2-Deoxy-D-erythro-pentose
    • Gold, A.; Sangaiah, R. 1,3,5-Tri-O-acetyl-2-deoxy-α,β-D-erythro-pentofuranose from 2-Deoxy-D-erythro-pentose. Nucleosides Nucleotides 1990, 9, 907-912.
    • (1990) Nucleosides Nucleotides , vol.9 , pp. 907-912
    • Gold, A.1    Sangaiah, R.2
  • 35
    • 1542432406 scopus 로고
    • On the Conversion of Arabino- and Ribofuranosyl Methyl Glycosides to Their 1-O-Acetyl Derivatives
    • Cimpoia, A. R.; Hunter, P. J.; Evans, C. A.; Jin, H.; Breining, T.; Mansour, T. S. On the Conversion of Arabino- and Ribofuranosyl Methyl Glycosides to Their 1-O-Acetyl Derivatives. J. Carbohydr. Chem. 1994, 13, 1115-1119.
    • (1994) J. Carbohydr. Chem. , vol.13 , pp. 1115-1119
    • Cimpoia, A.R.1    Hunter, P.J.2    Evans, C.A.3    Jin, H.4    Breining, T.5    Mansour, T.S.6
  • 36
    • 15144338642 scopus 로고
    • Acetolysis: The Formation of Acyclic Byproducts
    • Bischofberger, K.; Hall, R. H. Acetolysis: The Formation of Acyclic Byproducts. Carbohydr. Res. 1975, 42, 175-179.
    • (1975) Carbohydr. Res. , vol.42 , pp. 175-179
    • Bischofberger, K.1    Hall, R.H.2
  • 37
    • 15144352757 scopus 로고
    • 9-α-D-Xylofuranosyladenine. Acetolysis of 3,5-di-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose
    • Magnani, A.; Mikuriya, Y. 9-α-D-Xylofuranosyladenine. Acetolysis of 3,5-di-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose. Carbohydr. Res. 1973, 28, 158-164.
    • (1973) Carbohydr. Res. , vol.28 , pp. 158-164
    • Magnani, A.1    Mikuriya, Y.2
  • 38
    • 15144347269 scopus 로고
    • 1,2-Di-O-acetyl-5-O-benzoyl-3-deoxy-3-fluoro-D-xylofuranose. A Versatile Precursor for the Synthesis of 3-Deoxy-3-fluoro-β-D-xylofuranosyl Nucleosides as Potential Antiviral Agents
    • Gosselin, G.; Puech, F.; Genu-Dellac, C.; Imbach, J.-L. 1,2-Di-O-acetyl-5-O-benzoyl-3-deoxy-3-fluoro-D-xylofuranose. A Versatile Precursor for the Synthesis of 3-Deoxy-3-fluoro-β-D-xylofuranosyl Nucleosides as Potential Antiviral Agents. Carbohydr. Res. 1993, 42, 175-179.
    • (1993) Carbohydr. Res. , vol.42 , pp. 175-179
    • Gosselin, G.1    Puech, F.2    Genu-Dellac, C.3    Imbach, J.-L.4
  • 39
    • 0024314580 scopus 로고
    • Assignment of Anomeric Configuration of D-Ribo-Arabino-2′-Deoxyribo-, and 2′,3′-Dideoxy-ribonucleotides by NOE Difference Spectroscopy
    • Rosemeyer, H.; Toth, G.; Seela, F. Assignment of Anomeric Configuration of D-Ribo-Arabino-2′-Deoxyribo-, and 2′,3′-Dideoxy-ribonucleotides by NOE Difference Spectroscopy. Nucleosides Nucleotides 1989, 8, 587-597.
    • (1989) Nucleosides Nucleotides , vol.8 , pp. 587-597
    • Rosemeyer, H.1    Toth, G.2    Seela, F.3
  • 40
    • 0002633469 scopus 로고
    • A General Method of Synthesis and Isolation, and an NMR-Spectroscopic Study, of Tetra-O-acetyl-D-aldopentofuranoses
    • Kam, B. L.; Barascut, J.-L.; Imbach, J.-L. A General Method of Synthesis and Isolation, and an NMR-Spectroscopic Study, of Tetra-O-acetyl-D-aldopentofuranoses. Carbohydr. Res. 1979, 69, 135-142.
    • (1979) Carbohydr. Res. , vol.69 , pp. 135-142
    • Kam, B.L.1    Barascut, J.-L.2    Imbach, J.-L.3
  • 41
    • 0017073707 scopus 로고
    • Antiviral Activity of Arabinofuranosyladenine and Arabinofuranosylhypoxanthine in Herpes Simplex Virus-Infected KB Cells. I. Selective Inhibition of Viral DNA Synthesis in Synchronized Suspension Cultures
    • Shipman, C., Jr.; Smith, S. H.; Carlson, R. H.; Drach, J. C. Antiviral Activity of Arabinofuranosyladenine and Arabinofuranosylhypoxanthine in Herpes Simplex Virus-Infected KB Cells. I. Selective Inhibition of Viral DNA Synthesis in Synchronized Suspension Cultures. 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
  • 43
    • 0025304011 scopus 로고
    • A Microtiter Virus Yield Reduction Assay for the Evaluation of Antiviral Compounds Against Human Cytomegalovirus and Herpes Simplex Virus
    • Prichard, M. N.; Turk, S. R.; Coleman, L. A.; Engelhardt, S. L.; Shipman, C., Jr.; Drach, J. C. A Microtiter Virus Yield Reduction Assay for the Evaluation of Antiviral Compounds Against Human Cytomegalovirus and Herpes Simplex Virus. J. Virol. Methods 1990, 28, 101-106.
    • (1990) J. Virol. Methods , vol.28 , pp. 101-106
    • Prichard, M.N.1    Turk, S.R.2    Coleman, L.A.3    Engelhardt, S.L.4    Shipman Jr., C.5    Drach, J.C.6
  • 44
    • 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
  • 45
    • 0025756141 scopus 로고
    • Three-Dimensional Analysis of the Synergistic Cytotoxicity of Ganciclovir and Zidovudine
    • Prichard, M. N.; Prichard, L. E.; Baguley, W. A.; Nassiri, M. R.; Shipman, C., Jr. Three-Dimensional Analysis of the 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, M.R.4    Shipman Jr., C.5
  • 46
    • 15144349557 scopus 로고    scopus 로고
    • Unpublished data from our laboratory
    • Unpublished data from our laboratory.
  • 47
    • 15144357426 scopus 로고    scopus 로고
    • 1H NMR) confirmed that 1 mol of dichloromethane was present for every 12 mol of 18
    • 1H NMR) confirmed that 1 mol of dichloromethane was present for every 12 mol of 18.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.