메뉴 건너뛰기




Volumn 40, Issue 5, 1997, Pages 802-810

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

Author keywords

[No Author keywords available]

Indexed keywords

4,5 DICHLORO 1 BETA D RIBOFURANOSYLBENZIMIDAZOLE DERIVATIVE; 4,6 DICHLORO 1 BETA D RIBOFURANOSYLBENZIMIDAZOLE DERIVATIVE; ANTIVIRUS AGENT; BENZIMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0031048289     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960533b     Document Type: Article
Times cited : (30)

References (39)
  • 1
    • 85069106897 scopus 로고
    • Synthesis and Antiviral Activity of 1-β-D-Ribofuranosyl-2,4,6-trichlorobenzimidazole. A part of this work has been
    • Boston, MA, Apr 22
    • Zou, R.; Drach, J. C.; Townsend, L. B. Synthesis and Antiviral Activity of 1-β-D-Ribofuranosyl-2,4,6-trichlorobenzimidazole. A part of this work has been presented at the 199th ACS national meeting, Boston, MA, Apr 22, 1990.
    • (1990) 199th ACS National Meeting
    • Zou, R.1    Drach, J.C.2    Townsend, L.B.3
  • 2
    • 0023909230 scopus 로고
    • Serious Cytomegalovirus Disease in the Acquired Immunodeficiency Syndrome (AIDS), Clinical Findings, Diagnosis, and Treatment
    • Jacobson, M. A.; Mills, J. Serious Cytomegalovirus Disease in the Acquired Immunodeficiency Syndrome (AIDS), Clinical Findings, Diagnosis, and Treatment. Ann. Intern. Med. 1988, 108, 585-594.
    • (1988) Ann. Intern. Med. , vol.108 , pp. 585-594
    • Jacobson, M.A.1    Mills, J.2
  • 3
    • 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
  • 4
    • 0022621521 scopus 로고
    • Risk Factors for Cytomegalovirus Infection after Human Marrow Transplantation
    • Meyers, J. D.; Flournoy, N.; Thomas, E. D. Risk Factors for Cytomegalovirus Infection after Human Marrow Transplantation. J. Infect. Dis. 1986, 153, 478-488.
    • (1986) J. Infect. Dis. , vol.153 , pp. 478-488
    • Meyers, J.D.1    Flournoy, N.2    Thomas, E.D.3
  • 6
    • 0019644374 scopus 로고
    • Cytomegalovirus Infections Following Renal Transplantation
    • Glenn, J. Cytomegalovirus Infections Following Renal Transplantation. Rev. Infect. Dis. 1981, 3, 1151-1178.
    • (1981) Rev. Infect. Dis. , vol.3 , pp. 1151-1178
    • Glenn, J.1
  • 7
    • 0017285446 scopus 로고
    • Clinical Efficacy of Adenine Arabinoside in Therapy of Cytomegalovirus Infections in Renal Allograft Recipients
    • Rytel, M. W.; Kauffman, H. M. Clinical Efficacy of Adenine Arabinoside in Therapy of Cytomegalovirus Infections in Renal Allograft Recipients. J. Infect. Dis. 1976, 133, 202-205.
    • (1976) J. Infect. Dis. , vol.133 , pp. 202-205
    • Rytel, M.W.1    Kauffman, H.M.2
  • 9
    • 0019975811 scopus 로고
    • Treatment of Cytomegalovirus Pneumonia after Marrow Transplant with Combined Vidarabine and Human Leukocyte Interferon
    • Meyers, J. D.; McGuffin, R. W.; Bryson, Y. J.; Cantell, K.; Thomas, E. D. Treatment of Cytomegalovirus Pneumonia after Marrow Transplant with Combined Vidarabine and Human Leukocyte Interferon. J. Infect. Dis. 1982, 146, 80-84.
    • (1982) J. Infect. Dis. , vol.146 , pp. 80-84
    • Meyers, J.D.1    McGuffin, R.W.2    Bryson, Y.J.3    Cantell, K.4    Thomas, E.D.5
  • 10
    • 0020503247 scopus 로고
    • Treatment of Cytomegalovirus Pneumonia with High-Dose Acyclovir and Human Leukocyte Interferon
    • Wade, J. C.; McGuffin, R. W.; Springmeyer, S. C.; Newton, B.; Singer, J. W.; Meyers, J. D. Treatment of Cytomegalovirus Pneumonia with High-Dose Acyclovir and Human Leukocyte Interferon. J. Infect. Dis. 1983, 148, 557-562.
    • (1983) J. Infect. Dis. , vol.148 , pp. 557-562
    • Wade, J.C.1    McGuffin, R.W.2    Springmeyer, S.C.3    Newton, B.4    Singer, J.W.5    Meyers, J.D.6
  • 11
    • 0023943893 scopus 로고
    • Antiviral Chemotherapy for Cytomegalovirus Disease
    • (a) Morris, D. J. Antiviral Chemotherapy for Cytomegalovirus Disease. J. Antimicrob. Chemother. 1988, 21, 519-522.
    • (1988) J. Antimicrob. Chemother. , vol.21 , pp. 519-522
    • Morris, D.J.1
  • 12
    • 0342652438 scopus 로고
    • Therapy and Prevention of Cytomegalovirus Infections
    • DeClercq, E., Ed.; Martinus Nijhoff Publishing: Norwell
    • (b) Skolnik P. R.; Hirsch, M. S. Therapy and Prevention of Cytomegalovirus Infections. In Clinical Use of Antiviral Drugs; DeClercq, E., Ed.; Martinus Nijhoff Publishing: Norwell, 1988; pp 159-194.
    • (1988) Clinical Use of Antiviral Drugs , pp. 159-194
    • Skolnik, P.R.1    Hirsch, M.S.2
  • 13
    • 0025233918 scopus 로고
    • Ganciclovir. A Review of its Antiviral Activity, Pharmacokinetic Properties and Therapeutic Efficacy in Cytomegalovirus Infections
    • Faulds, D.; Heel, R. C. Ganciclovir. A Review of its Antiviral Activity, Pharmacokinetic Properties and Therapeutic Efficacy in Cytomegalovirus Infections. Drugs 1990, 39, 597-638.
    • (1990) Drugs , vol.39 , pp. 597-638
    • Faulds, D.1    Heel, R.C.2
  • 14
    • 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
  • 15
    • 0028958136 scopus 로고
    • Phase VII study of intravitreal cidofovir for the treatment of cytomegalovirus retinitis in patients with the acquired immunodeficiency syndrome
    • (a) Kirsch, L. S.; Arevalo J. F.; De Clercq, E.; Chavez de la Paz, E.; Munguia, D.; Garcia, R.; Freeman, W. R. Phase VII study of intravitreal cidofovir for the treatment of cytomegalovirus retinitis in patients with the acquired immunodeficiency syndrome. Am. J. Ophthalmol. 1995, 119, 466-476.
    • (1995) Am. J. Ophthalmol. , vol.119 , pp. 466-476
    • Kirsch, L.S.1    Arevalo, J.F.2    De Clercq, E.3    Chavez De La Paz, E.4    Munguia, D.5    Garcia, R.6    Freeman, W.R.7
  • 17
    • 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
  • 18
    • 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
  • 19
    • 0028853743 scopus 로고
    • Design, Synthesis and Antiviral Activity of Certain 2,5,6-trihalo-1-(β-D-ribofuranosyl)- Benzimidazoles
    • (a) 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
  • 20
    • 0345672420 scopus 로고
    • Benzimidazole Ribonucleosides: Design, Synthesis, and Evaluation of 2,5,6-Trichloro-1-(β-D-ribofuranosyl)benzimidazole (TCRB), 2-Bromo-5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole (BDCRB), and Some Structurally Related Analogs as Agents for Human Cytomegalovirus Infections
    • Vancouver, B.C., Canada, 8-13 March
    • (b) Townsend, L. B. Benzimidazole Ribonucleosides: Design, Synthesis, and Evaluation of 2,5,6-Trichloro-1-(β-D-ribofuranosyl)benzimidazole (TCRB), 2-Bromo-5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole (BDCRB), and Some Structurally Related Analogs as Agents for Human Cytomegalovirus Infections. Fifth International Conference on Antiviral Research, Vancouver, B.C., Canada, 8-13 March, 1992.
    • (1992) Fifth International Conference on Antiviral Research
    • Townsend, L.B.1
  • 22
    • 0344400941 scopus 로고    scopus 로고
    • Comparison of Benzimidazole Nucleosides and Ganciclovir on the in Vitro proliferation and Colony Formation of Human Bone Marrow Progenitor Cells
    • Nassiri, M. R.; Emerson, S. G.; Townsend, L. B.; Drach, J. C.; Taichman, R. S. Comparison of Benzimidazole Nucleosides and Ganciclovir on the In Vitro proliferation and Colony Formation of Human Bone Marrow Progenitor Cells. Br. J. Haematol. 1996, 93, 273-279.
    • (1996) Br. J. Haematol. , vol.93 , pp. 273-279
    • Nassiri, M.R.1    Emerson, S.G.2    Townsend, L.B.3    Drach, J.C.4    Taichman, R.S.5
  • 24
    • 0346495323 scopus 로고
    • Inhibition of HCMV DNA Processing by a New Class of Anti-HCMV Compounds is Mediated Through the UL89 Gene Product
    • Vancouver, B.C., August
    • (b) Underwood, M. R.; Stanat, S. C.; Drach, J. C.; Harvey R. J.; Biron, K. K. Inhibition of HCMV DNA Processing by a New Class of Anti-HCMV Compounds is Mediated Through the UL89 Gene Product. Herpesvirus Workshop, Vancouver, B.C., August 1994.
    • (1994) Herpesvirus Workshop
    • Underwood, M.R.1    Stanat, S.C.2    Drach, J.C.3    Harvey, R.J.4    Biron, K.K.5
  • 25
    • 9544246519 scopus 로고
    • Benzimidazoles II. Effect of Benzene Nucleus substituents on the Nucleophilic Reactivity of Some 2-Chlorobenzimidazoles
    • Ricci A.; Vivarelli, P. Benzimidazoles II. Effect of Benzene Nucleus substituents on the Nucleophilic Reactivity of Some 2-Chlorobenzimidazoles. Gazz. Chim. Ital. 1967, 97, 750-757. Chem. Abstr. 1967, 67, 108597x.
    • (1967) Gazz. Chim. Ital. , vol.97 , pp. 750-757
    • Ricci, A.1    Vivarelli, P.2
  • 26
    • 9544224812 scopus 로고
    • Ricci A.; Vivarelli, P. Benzimidazoles II. Effect of Benzene Nucleus substituents on the Nucleophilic Reactivity of Some 2-Chlorobenzimidazoles. Gazz. Chim. Ital. 1967, 97, 750-757. Chem. Abstr. 1967, 67, 108597x.
    • (1967) Chem. Abstr. , vol.67
  • 27
    • 0014848447 scopus 로고
    • Synthesen von Benzimidazolonen and Polychlorierten Benzimidazolen
    • Rochling, H.; Frasca, E.; Buchel, K. H. Synthesen von Benzimidazolonen and Polychlorierten Benzimidazolen. Z. Naturforsch. 1970, 25b, 954-960.
    • (1970) Z. Naturforsch. , vol.25 B , pp. 954-960
    • Rochling, H.1    Frasca, E.2    Buchel, K.H.3
  • 30
    • 15444344614 scopus 로고
    • Some Dichloro- and Dibromo-derivatives of 1:2:3:4-Tetrahydrophenazine and cis-1:2:3:4:5:10: 11:12-Octahydrophenazine
    • Scott, R. M.; Tomlinson, M. Some Dichloro- and Dibromo-derivatives of 1:2:3:4-Tetrahydrophenazine and cis-1:2:3:4:5:10: 11:12-Octahydrophenazine. J. Chem. Soc. 1959, 417-420.
    • (1959) J. Chem. Soc. , pp. 417-420
    • Scott, R.M.1    Tomlinson, M.2
  • 31
    • 0001545332 scopus 로고
    • Puromycin Synthetic Studies. V. 6-Dimethylamino-9-(2′-Acetamino-β-D-Glucopyranosyl)purine
    • Baker, B. R.; Joseph, J. P.; Schaub, R. E.; Williams, J. H. Puromycin Synthetic Studies. V. 6-Dimethylamino-9-(2′-Acetamino-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
  • 33
    • 0024314580 scopus 로고
    • Assignment of Anomeric Configuration of D-Ribo, Arabino-, 2′-Deoxyribo-, and 2′,3′-Dideoxyribonucleosides by NOE Difference Spectroscopy
    • Rosemeyer, H.; Toth, G.; Seela, F. Assignment of Anomeric Configuration of D-Ribo, Arabino-, 2′-Deoxyribo-, and 2′,3′-Dideoxyribonucleosides 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
  • 34
    • 10244269473 scopus 로고
    • Unambiguous Assignment of Anomeric Configuration of Nucleosides by NOE-Difference Spectroscopy
    • Toth, G.; Rosemeyer, H.; Seela, F. Unambiguous Assignment of Anomeric Configuration of Nucleosides by NOE-Difference Spectroscopy. Nucleosides Nucleotides 1989, 8, 1091-1092.
    • (1989) Nucleosides Nucleotides , vol.8 , pp. 1091-1092
    • Toth, G.1    Rosemeyer, H.2    Seela, F.3
  • 35
    • 0028129709 scopus 로고
    • Benzimidazole Ribonucleosides: Design, Synthesis and Antiviral Evaluation of Certain 2-alkylthio-5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazoles
    • Devivar, R. V.; Kawashima, E.; Revankar, G. R.; Breitenbach, J. M.; Drach, J.C.; Townsend, L. B. Benzimidazole Ribonucleosides: Design, Synthesis and Antiviral Evaluation of Certain 2-alkylthio-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    Drach, J.C.5    Townsend, L.B.6
  • 37
    • 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
  • 38
    • 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


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.