메뉴 건너뛰기




Volumn 40, Issue 5, 1997, Pages 785-793

Synthesis and antiviral activity of certain 5'-modified analogs of 2,5,6-trichloro-1-(β-D-ribofuranosyl)benzimidazole

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; BENZIMIDAZOLE DERIVATIVE; RIBONUCLEOSIDE DERIVATIVE;

EID: 0031052117     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9604888     Document Type: Article
Times cited : (24)

References (45)
  • 2
    • 0001947969 scopus 로고
    • Cytomegalovirus
    • Roizman, B., Whitley, R. J., Lopez, C., Eds.; Raven Press: New York
    • (b) Alford, C. A.; Britt, W. J. Cytomegalovirus. In The Human Cytomegalovirus, Roizman, B., Whitley, R. J., Lopez, C., Eds.; Raven Press: New York, 1993; pp 227-255.
    • (1993) The Human Cytomegalovirus , pp. 227-255
    • Alford, C.A.1    Britt, W.J.2
  • 3
    • 0025146372 scopus 로고
    • Cytomegalovirus Infections in Bone Marrow Transplant Recipients Given Intensive Cytoreductive Therapy
    • Wingard, J. R.; Piantadosi, S.; Burns, W. H.; Zahurak, M. L.; Santos, G. W.; Saral, R. Cytomegalovirus Infections in Bone Marrow Transplant Recipients Given Intensive Cytoreductive Therapy. Rev. Infect. Dis. 1990, 12, S793-S804.
    • (1990) Rev. Infect. Dis. , vol.12
    • Wingard, J.R.1    Piantadosi, S.2    Burns, W.H.3    Zahurak, M.L.4    Santos, G.W.5    Saral, R.6
  • 4
    • 0025946562 scopus 로고
    • The Cause of Death in Patients with Human Immunodeficiency Virus Infection: A Clinical and Pathological Study with Emphasis on the Role of Pulmonary Diseases
    • (a) McKenzie, R.; Travis, W. D.; Dolan, S. A.; Pittaluga, S.; Feuerstein, I. M.; Shelhamer, J.; Yarchoan, R.; Masur, H. The Cause of Death in Patients with Human Immunodeficiency Virus Infection: A Clinical and Pathological Study with Emphasis on the Role of Pulmonary Diseases. Medicine 1991, 70, 326-343.
    • (1991) Medicine , vol.70 , pp. 326-343
    • McKenzie, R.1    Travis, W.D.2    Dolan, S.A.3    Pittaluga, S.4    Feuerstein, I.M.5    Shelhamer, J.6    Yarchoan, R.7    Masur, H.8
  • 5
    • 0024504361 scopus 로고
    • Cytomegalovirus in the Nervous System of Patients with the Acquired Immune Deficiency Syndrome
    • (b) Vinters, H. V.; Kwok, M. K.; Ho, H. W. Cytomegalovirus in the Nervous System of Patients with the Acquired Immune Deficiency Syndrome. Brain 1989, 112, 245-268.
    • (1989) Brain , vol.112 , pp. 245-268
    • Vinters, H.V.1    Kwok, M.K.2    Ho, H.W.3
  • 7
    • 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
  • 8
    • 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
  • 9
    • 0024373015 scopus 로고
    • Synthesis and Antiviral Activity of the Nucleotide Analogue (S)-1-[3-Hydroxy-2-(phosphonylmethoxy)propyl]-cytosine
    • (a) Bronson, J. J.; Ghazzouli, I.; Hitchcock, M. J. M.; Webb, R. R.; Martin, J. C. Synthesis and Antiviral Activity of the Nucleotide Analogue (S)-1-[3-Hydroxy-2-(phosphonylmethoxy)propyl]-cytosine. J. Med. Chem. 1989, 32, 1457-1463.
    • (1989) J. Med. Chem. , vol.32 , pp. 1457-1463
    • Bronson, J.J.1    Ghazzouli, I.2    Hitchcock, M.J.M.3    Webb, R.R.4    Martin, J.C.5
  • 11
    • 0028156908 scopus 로고
    • "The End of Innocence" Revisited: Resistance to Antiviral Drugs
    • Field, A. K.; Biron, K. K. "The End of Innocence" Revisited: Resistance 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
  • 12
    • 0014803750 scopus 로고
    • Benzimidazole Nucleosides, Nucleotides, and Related Derivatives
    • (a) Revankar, G. R.; Townsend, L. B. Benzimidazole Nucleosides, Nucleotides, and Related Derivatives. Chem. Rev. 1970, 70, 389-438.
    • (1970) Chem. Rev. , vol.70 , pp. 389-438
    • Revankar, G.R.1    Townsend, L.B.2
  • 13
    • 84981856168 scopus 로고
    • The Synthesis of 2-Chloro-1-(β-D-ribofuranosyl)benzimidazole and Certain Related Derivatives
    • (b) Revankar, G. R.; Townsend, L. B. The Synthesis of 2-Chloro-1-(β-D-ribofuranosyl)benzimidazole and Certain Related Derivatives. J. Heterocycl. Chem. 1968, 5, 477-483.
    • (1968) J. Heterocycl. Chem. , vol.5 , pp. 477-483
    • Revankar, G.R.1    Townsend, L.B.2
  • 14
    • 0026441495 scopus 로고
    • Benzimidazole Ribonucleosides: Observation of an Unexpected Nitration when Performing Nonaqueous Diazotizations with t-Butyl Nitrate
    • (a) Devivar, R. V.; Drach J. C.; Townsend, L. B. Benzimidazole Ribonucleosides: Observation of an Unexpected Nitration when Performing Nonaqueous Diazotizations with t-Butyl Nitrate. Bioorg. Med. Chem. Lett. 1992, 2, 1105-1110.
    • (1992) Bioorg. Med. Chem. Lett. , vol.2 , pp. 1105-1110
    • Devivar, R.V.1    Drach, J.C.2    Townsend, L.B.3
  • 15
    • 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
    • (b) 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
  • 16
    • 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
  • 19
    • 1542552452 scopus 로고
    • The Benzimidazole Riboside, 2-Bromo-5,6-dichloro-1-β-D-ribofuranosyl Benzimidazole (BDCRB), Prevents Maturation of Concatemeric Viral DNA in HCMV-Infected Cells
    • Institut Pasteur, Paris, France, April
    • (a) Underwood, M. R.; Biron, K. K.; Hemphill, M. L.; Miller, T. J.; Stanat, S. C.; Drach, J. C.; Townsend, L. B.; Harvey, R. J. The Benzimidazole Riboside, 2-Bromo-5,6-dichloro-1-β-D-ribofuranosyl Benzimidazole (BDCRB), Prevents Maturation of Concatemeric Viral DNA in HCMV-Infected Cells. 4th International CMV Conference, Institut Pasteur, Paris, France, April 1993.
    • (1993) 4th International CMV Conference
    • Underwood, M.R.1    Biron, K.K.2    Hemphill, M.L.3    Miller, T.J.4    Stanat, S.C.5    Drach, J.C.6    Townsend, L.B.7    Harvey, R.J.8
  • 21
    • 0346495323 scopus 로고
    • Inhibition of HCMV DNA Processing by a New Class of Anti-HCMV Compounds is Mediated Through the UL89 Gene Product
    • Vancouver, British Columbia, Canada, August
    • (c) 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, British Columbia, Canada, 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
  • 22
    • 1542657432 scopus 로고
    • Inhibition of HCMV DNA Processing by a New Class of Anti-HCMV Compounds (Benzimidazole Ribosides) is Mediated through the UL89 Gene Product
    • Santa Fe, NM, April
    • (d) Underwood, M. R.; Stanat, S. C.; Townsend, L. B.; Drach, J. C.; Biron, K. K. Inhibition of HCMV DNA Processing by a New Class of Anti-HCMV Compounds (Benzimidazole Ribosides) is Mediated through the UL89 Gene Product. 8th International Conference on Antiviral Research, Santa Fe, NM, April 1995.
    • (1995) 8th International Conference on Antiviral Research
    • Underwood, M.R.1    Stanat, S.C.2    Townsend, L.B.3    Drach, J.C.4    Biron, K.K.5
  • 23
    • 0030067363 scopus 로고    scopus 로고
    • Structure Activity Relationships among 2-Substituted 5,6-Dichloro-, 4,6-Dichloro-, and 4,5-Dichloro-1-(2-hydroxyethoxymethyl)- and 1-[(1,3-dihydroxy-2-propoxy)methyl]benzimidazoles
    • Saluja, S.; Zou, R.; Drach, J. C.; Townsend, L. B. Structure Activity Relationships Among 2-Substituted 5,6-Dichloro-, 4,6-Dichloro-, and 4,5-Dichloro-1-(2-hydroxyethoxymethyl)- and 1-[(1,3-dihydroxy-2-propoxy)methyl]benzimidazoles. J. Med. Chem. 1996, 39, 881-892.
    • (1996) J. Med. Chem. , vol.39 , pp. 881-892
    • Saluja, S.1    Zou, R.2    Drach, J.C.3    Townsend, L.B.4
  • 25
    • 84982058693 scopus 로고
    • On the Mechanism of Nucleoside Synthesis
    • Vorbruggen, H.; Hofle, G. On the Mechanism of Nucleoside Synthesis. Chem. Ber. 1981, 114, 1256-1268.
    • (1981) Chem. Ber. , vol.114 , pp. 1256-1268
    • Vorbruggen, H.1    Hofle, G.2
  • 26
    • 0000453219 scopus 로고
    • Design and Reactivity of Organic Functional Groups- 2-Pyridylsulfonates as Nucleofugal Esters: Remarkably Mild Transformation into Halides and Olefins
    • Hanessian, S.; Kagotani, M.; Komaglou, K. Design and Reactivity of Organic Functional Groups- 2-Pyridylsulfonates as Nucleofugal Esters: Remarkably Mild Transformation into Halides and Olefins. Heterocycles 1989, 28, 1115-1120.
    • (1989) Heterocycles , vol.28 , pp. 1115-1120
    • Hanessian, S.1    Kagotani, M.2    Komaglou, K.3
  • 27
    • 0001069018 scopus 로고
    • 5-Deoxy-5-fluoro-D-ribofuranosyl Derivatives of Certain Purines, Pyrimidines and 5,6-Dimethyl-benzimidazole
    • Kissman, H. M.; Weiss, M. J. 5-Deoxy-5-fluoro-D-ribofuranosyl Derivatives of Certain Purines, Pyrimidines and 5,6-Dimethyl-benzimidazole. J. Chem. Soc. 1958, 80, 5559-5564.
    • (1958) J. Chem. Soc. , vol.80 , pp. 5559-5564
    • Kissman, H.M.1    Weiss, M.J.2
  • 28
    • 0000713372 scopus 로고
    • New Halogenation Reagent Systems Useful for the Mild One-Step Conversion of Alcohols into Iodides or Bromides
    • Classon, B.; Liu, Z. New Halogenation Reagent Systems Useful for the Mild One-Step Conversion of Alcohols into Iodides or Bromides. J. Org. Chem. 1988, 53, 6126-6130.
    • (1988) J. Org. Chem. , vol.53 , pp. 6126-6130
    • Classon, B.1    Liu, Z.2
  • 29
    • 0001666695 scopus 로고
    • The Synthesis of Certain 5-Deoxy-D-ribofuranosylpurines
    • Kissman, H. M.; Baker, B. R. The Synthesis of Certain 5-Deoxy-D-ribofuranosylpurines. J. Am. Chem. Soc. 1957, 79, 5534-5540.
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 5534-5540
    • Kissman, H.M.1    Baker, B.R.2
  • 30
    • 1942433689 scopus 로고
    • D-Ribose Derivatives. II. Preperation of 2,3-Di-O-acetyl-5-deoxy-5-iodoribofuranosyl Chloride from 5-O-Triphenylmethyl-D-ribose
    • Kanazawa, T.; Sato, T. D-Ribose Derivatives. II. Preperation of 2,3-Di-O-acetyl-5-deoxy-5-iodoribofuranosyl Chloride from 5-O-Triphenylmethyl-D-ribose. Nippon Kagaku Zasshi 1059, 80, 200-203.
    • (1059) Nippon Kagaku Zasshi , vol.80 , pp. 200-203
    • Kanazawa, T.1    Sato, T.2
  • 32
    • 0010114002 scopus 로고
    • A Synthesis of (-)-Slaframine and (-)-1,8a-Diepislaframine
    • Pearson, W. H.; Bergmeier, S. C. A Synthesis of (-)-Slaframine and (-)-1,8a-Diepislaframine. J. Org. Chem. 1991, 56, 1976-1978.
    • (1991) J. Org. Chem. , vol.56 , pp. 1976-1978
    • Pearson, W.H.1    Bergmeier, S.C.2
  • 33
    • 85077634689 scopus 로고
    • The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products
    • Mitsunobo, O. The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products. Synthesis 1981, 1-28.
    • (1981) Synthesis , pp. 1-28
    • Mitsunobo, O.1
  • 34
    • 0016259814 scopus 로고
    • Analogs of 5′-Deoxy-5′-(methylthio)adenosine
    • (a) Montgomery, J. A.; Shortnacy, A. T.; Thomas, H. J. Analogs of 5′-Deoxy-5′-(methylthio)adenosine. J. Med. Chem. 1974, 17, 1197-1209.
    • (1974) J. Med. Chem. , vol.17 , pp. 1197-1209
    • Montgomery, J.A.1    Shortnacy, A.T.2    Thomas, H.J.3
  • 35
    • 14444275561 scopus 로고
    • A New Synthesis of 9-β-(5′-thiomethyl-D-ribofuranosyl)adenine
    • (b) Kanazawa, T. A New Synthesis of 9-β-(5′-thiomethyl-D-ribofuranosyl)adenine. Nippon Kagaku Zasshi 1960, 81, 516-517.
    • (1960) Nippon Kagaku Zasshi , vol.81 , pp. 516-517
    • Kanazawa, T.1
  • 38
    • 0002714675 scopus 로고
    • Rapid Chromatographic Techniques for Preparative Separation with Moderate Resolution
    • Still, W. C.; Kahn, M.; Mitra, A. Rapid Chromatographic Techniques for Preparative Separation with Moderate Resolution. J. Org. Chem. 1978, 43, 2923-2925.
    • (1978) J. Org. Chem. , vol.43 , pp. 2923-2925
    • Still, W.C.1    Kahn, M.2    Mitra, A.3
  • 40
    • 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
  • 42
    • 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
  • 43
    • 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
  • 44
    • 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
  • 45
    • 0025899234 scopus 로고
    • Use of an Aqueous Soluble Tetrazolium/Formazan Assay for Cell Growth Assays in Culture
    • Cory, A. H.; Owen, T. C.; Barltrop, J. A.; Cory, J. G. Use of an Aqueous Soluble Tetrazolium/Formazan Assay for Cell Growth Assays in Culture. Cancer Commun. 1991, 3, 207-212.
    • (1991) Cancer Commun. , vol.3 , pp. 207-212
    • Cory, A.H.1    Owen, T.C.2    Barltrop, J.A.3    Cory, J.G.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.