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Volumn 19, Issue 1-2, 2000, Pages 125-153

Design, synthesis, and antiviral evaluation of 2-deoxy-D-ribosides of substituted benzimidazoles as potential agents for human cytomegalovirus infections

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 DEOXY BETA DEXTRO ERYTHRO PENTOFURANOSYL) 5,6 DICHLORO 2 ISOPROPYLAMINOBENZIMIDAZOLE; 2 AMINO 5,6 DICHLORO 1 (2 DEOXY BETA DEXTRO ERYTHRO PENTOFURANOSYL)BENZIMIDAZOLE; 2 AZIDO 5,6 DICHLORO 1 (2 DEOXY BETA DEXTRO ERYTHRO PENTOFURANOZYL)BENZIMIDAZOLE; 2 BROMO 5,6 DICHLORO 1 (2 DEOXY BETA DEXTRO ERYTHRO PENTOFURANOSYL)BENZIMIDAZOLE; 2,5,6 TRICHLORO 1 (2 DEOXY BETA DEXTRO ERYTHRO PENTOFURANOSYL)BENZIMIDAZOLE; 2,5,6 TRICHLORO 1 BETA DEXTRO RIBOFURANOSYLBENZIMIDAZOLE; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0034110178     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1080/15257770008033000     Document Type: Article
Times cited : (18)

References (39)
  • 1
    • 0001450002 scopus 로고    scopus 로고
    • Cytomegalovirus
    • B.N. Fields, D.M. Knipe, and P.M. Howley (ed.), Lippincott - Raven Publishers, Philadelphia, PA
    • Britt, W. J.; Alford, C. A. Cytomegalovirus, p 2493-2523. In B.N. Fields, D.M. Knipe, and P.M. Howley (ed.), Fields Virology, 3rd ed., 1996. Lippincott - Raven Publishers, Philadelphia, PA.
    • (1996) Fields Virology, 3rd Ed. , pp. 2493-2523
    • Britt, W.J.1    Alford, C.A.2
  • 3
    • 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
  • 5
    • 0032500293 scopus 로고    scopus 로고
    • First "antisense" drug will treat CMV retinitis
    • Marwick, C. First "antisense" drug will treat CMV retinitis. J. Amer. Med. Assn. 1998 280:871.
    • (1998) J. Amer. Med. Assn. , vol.280 , pp. 871
    • Marwick, C.1
  • 6
    • 0342652438 scopus 로고
    • Therapy and prevention of cytomegalovirus infections
    • DeClercq, E. Ed., Martinus Nijhoff Publishing, Norwell
    • 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
  • 8
    • 0023555690 scopus 로고
    • Immunosuppressive effects of Ganciclovir on in vitro lymphocyte responses
    • Bowden, R. A.; Digel, J.; Reed, E. C.; Meyers, J. D. Immunosuppressive Effects of Ganciclovir on in vitro Lymphocyte Responses. J. Infect. Dis. 1987, 156, 899-903.
    • (1987) J. Infect. Dis. , vol.156 , pp. 899-903
    • Bowden, R.A.1    Digel, J.2    Reed, E.C.3    Meyers, J.D.4
  • 9
    • 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. Clinical Microbiology Reviews 1994; 7:1-13.
    • (1994) Clinical Microbiology Reviews , vol.7 , pp. 1-13
    • Field, A.K.1    Biron, K.K.2
  • 10
    • 0014803750 scopus 로고
    • Benzimidazole nucleosides, nucleotides, and related derivatives
    • (a) 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
  • 11
    • 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
  • 12
    • 0003705490 scopus 로고
    • The chemistry of anti-pernicious anaemia factors Part III. 5:6-disubstituted benzimidazoles as products of acid hydrolysis of vitamin B12
    • Beavan, G. R.; Holiday, E. R.; Johnson, E. A.; Ellis, B.; Mamalis, P.; Petrow, V.; Sturgeon, B. The chemistry of anti-pernicious anaemia factors Part III. 5:6-Disubstituted benzimidazoles as products of acid hydrolysis of vitamin B12. Journal of Pharmacy and Pharmacology 1949; 1:957-970.
    • (1949) Journal of Pharmacy and Pharmacology , vol.1 , pp. 957-970
    • Beavan, G.R.1    Holiday, E.R.2    Johnson, E.A.3    Ellis, B.4    Mamalis, P.5    Petrow, V.6    Sturgeon, B.7
  • 13
    • 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, 227-248.
    • (1954) J. Exp. Med. , vol.99 , pp. 227-248
    • Tamm, I.1    Folkers, K.2    Shunk, C.H.3    Horsfall F.L., Jr.4
  • 14
    • 0017915202 scopus 로고
    • Halobenzimidazole ribosides and RNA synthesis of cells and viruses
    • Tamm, I.; Sehgal, P. B. Halobenzimidazole ribosides and RNA synthesis of cells and viruses. Advances in Virus Research 1978; 22:187-258.
    • (1978) Advances in Virus Research , vol.22 , pp. 187-258
    • Tamm, I.1    Sehgal, P.B.2
  • 15
    • 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
  • 16
    • 0031052117 scopus 로고    scopus 로고
    • Synthesis and antiviral activity of certain 5′-modified analogs of 2,5,6,-trichloro-1-(ß-D-ribofuranosyl)benzimidazole (TCRB)
    • (b) 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-(ß-D-ribofuranosyl)benzimidazole (TCRB). 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
  • 17
    • 0031058374 scopus 로고    scopus 로고
    • Design, synthesis and antiviral evaluation of 2-chloro-5,6-dihalo-1-(ß-D-ribofuranosyl)benzimidazoles as potential agents for human cytomegalovirus infections
    • (c) Zou, R.; Drach, J. C.; Townsend, L.B. Design, synthesis and antiviral evaluation of 2-chloro-5,6-dihalo-1-(ß-D-ribofuranosyl)benzimidazoles 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
  • 18
    • 0031985103 scopus 로고    scopus 로고
    • Inhibition of human cytomegalovirus DNA maturation by a benzimidazole ribonucleoside is mediated through the UL89 gene product
    • Underwood, M. R.; Harvey, R. J.; Stanat, S. C.; Hemphill, M. L.; Miller, T.; Drach, J. C.; Townsend, L. B.; Biron, K. K. Inhibition of human cytomegalovirus DNA maturation by a benzimidazole ribonucleoside is mediated through the UL89 gene product. J. Virol. 1998, 72:717-725.
    • (1998) J. Virol. , vol.72 , pp. 717-725
    • Underwood, M.R.1    Harvey, R.J.2    Stanat, S.C.3    Hemphill, M.L.4    Miller, T.5    Drach, J.C.6    Townsend, L.B.7    Biron, K.K.8
  • 20
    • 0014331752 scopus 로고
    • Analogs of 3-amino-7-chloro-1,2,4-benzotriazine 1-oxide as antimalarial agents
    • Horner, J. K.; Henry, D. W. Analogs of 3-Amino-7-chloro-1,2,4-benzotriazine 1-Oxide as Antimalarial Agents. J. Med. Chem. 1968, 11, 946-949.
    • (1968) J. Med. Chem. , vol.11 , pp. 946-949
    • Horner, J.K.1    Henry, D.W.2
  • 24
    • 0006828761 scopus 로고
    • 12, purine, and pyrimidine requirement of lactobacillus leichmannii 313
    • 12, Purine, and Pyrimidine Requirement of Lactobacillus Leichmannii 313. Z. Naturforsch. 1951, 6b, 25-34.
    • (1951) Z. Naturforsch. , vol.6 B , pp. 25-34
    • Weygand, F.1    Wacker, A.2    Wirth, F.3
  • 25
    • 0014854403 scopus 로고
    • Inhibitors of photosynthesis VI, synthesis of electronegatively substituted benzimidazoles
    • Buchel, K. H. Inhibitors of Photosynthesis VI, Synthesis of Electronegatively Substituted Benzimidazoles. Z. Naturforsch. 1970, 25b, 945-953.
    • (1970) Z. Naturforsch. , vol.25 B , pp. 945-953
    • Buchel, K.H.1
  • 26
    • 0001912607 scopus 로고
    • Synthesis and study of 2-benzylthio benzothiazoles and 2-benzylthiobenzimidazoles as antituberculosis agents
    • Pande, A. V.; Kirke, P. A.; Khadse, B. G. Synthesis and Study of 2-Benzylthio benzothiazoles and 2-Benzylthiobenzimidazoles as Antituberculosis Agents. Bull. Haffkine Inst. 1983, 11, 51-55.
    • (1983) Bull. Haffkine Inst. , vol.11 , pp. 51-55
    • Pande, A.V.1    Kirke, P.A.2    Khadse, B.G.3
  • 27
    • 0343522612 scopus 로고
    • Benz- and naphthazole series. V. 5,6-dimethyl-2-hydrazinobenzimidazole and its N-alkylated derivatives
    • CA. 61: 8297a
    • Bednyagina, N. P.; Tyurenkova, G. N.; Panov, I. V. Benz- and Naphthazole Series. V. 5,6-Dimethyl-2-hydrazinobenzimidazole and its N-Alkylated Derivatives. Zh. Obshch. Khim. 1964, 34. 1575-1577. CA. 61: 8297a.
    • (1964) Zh. Obshch. Khim. , vol.34 , pp. 1575-1577
    • Bednyagina, N.P.1    Tyurenkova, G.N.2    Panov, I.V.3
  • 28
    • 0000416466 scopus 로고
    • Preparation of a crystalline O-acyl-2-deoxypentofuranosyl halide
    • Zorbach, W. W.; Tipson, R. S. Eds. Interscience Publishers, New York
    • Bhat, C. C. Preparation of a Crystalline O-Acyl-2-deoxypentofuranosyl Halide. In "Synthetic Procedures in Nucleic Acid Chemistry", Vol. 1, Zorbach, W. W.; Tipson, R. S. Eds. Interscience Publishers, New York, 1968, pp. 521-522.
    • (1968) Synthetic Procedures in Nucleic Acid Chemistry , vol.1 , pp. 521-522
    • Bhat, C.C.1
  • 29
    • 33845470620 scopus 로고
    • Synthesis of 2′-deoxytubercidin, 2′-deoxyadenosine, and related 2′-deoxynucleosides via a novel direct stereospecific sodium salt glycosylation procedure
    • Kazimierczuk, Z.; Cottam, H. B.; Revankar, G. R.; Robins, R. K. Synthesis of 2′-Deoxytubercidin, 2′-Deoxyadenosine, and Related 2′-Deoxynucleosides via a Novel Direct Stereospecific Sodium Salt Glycosylation Procedure. J. Am. Chem. Soc. 1984, 706, 6379-6382.
    • (1984) J. Am. Chem. Soc. , vol.706 , pp. 6379-6382
    • Kazimierczuk, Z.1    Cottam, H.B.2    Revankar, G.R.3    Robins, R.K.4
  • 30
    • 0022123704 scopus 로고
    • Stereospecific synthesis by the sodium salt glycosylation method of halogeno benzimidazole 2′-deoxyribose analogues of the inhibitor of hnRNA synthesis, 5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole (DRB)
    • Kazimierczuk, Z.; Stolarski, R.; Shugar, D. Stereospecific Synthesis by the Sodium Salt Glycosylation Method of Halogeno Benzimidazole 2′-Deoxyribose Analogues of the Inhibitor of hnRNA Synthesis, 5,6-Dichloro-1-(β-D-ribofuranosyl)benzimidazole (DRB). Z. Naturforsch. 1985, 40c, 715-720.
    • (1985) Z. Naturforsch. , vol.40 C , pp. 715-720
    • Kazimierczuk, Z.1    Stolarski, R.2    Shugar, D.3
  • 31
    • 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.; Seala, 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    Seala, F.3
  • 36
    • 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 C., Jr.5    Drach, J.C.6
  • 37
    • 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 C., Jr.2
  • 38
    • 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 C., Jr.5
  • 39
    • 0025270735 scopus 로고
    • Crystallization and preliminary X-ray investigation of recombinant lactobacillus leichmannii nucleoside deoxyribosyltransferase
    • Cook, W. J.; Short, S. A.; Ealick, S. E. Crystallization and Preliminary X-ray Investigation of Recombinant Lactobacillus Leichmannii Nucleoside Deoxyribosyltransferase. Journal of Biological Chemistry 1990, 265, 2682-2683.
    • (1990) Journal of Biological Chemistry , vol.265 , pp. 2682-2683
    • Cook, W.J.1    Short, S.A.2    Ealick, S.E.3


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