Design, Synthesis and Antiviral Activity of α-L-Arabinofuranosyl Derivatives of 2-Substituted-5,6-dichlorobenzimidazoles

References

• Alford , C. A. , Britt and Cytomegalovirus , W. J. 1993 . The Human Herpesviruses , Edited by: Alford , C. A. and Britt , W. J. 227 – 255 . New York : Raven Press .
   Google Scholar
• Wingard , J. R. , Piantadosi , S. , Burns , W. H. , Zahurak , M. L. , Santos , G. W. and Saral , R. 1990 . Cytomegalovirus infections in bone marrow transplant recipients given intensive cytoredactive therapy . Rev. Infect. Dis. , 12 : S793 – S804 .
   Google Scholar
• McKenzie , R. , Travis , W. D. , Dolan , S. A. , Pittaluga , S. , Feuertein , I. M. , Shelhamer , J. , Yarchoan , R. and Masur , H. 1991 . 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 , 70 : 326
   PubMed Web of Science ®Google Scholar
• Britt , W. J. , Pass , R. F. , Stagno , S. and Alford , C. A. 1991 . Pediatric cytomegalovirus infection . Transplant. Proc. , 25 : 115 – 117 .
   Web of Science ®Google Scholar
• Crumpacker and Ganciclovir , C. S. 1996 . N. Engl. J. Med. , 335 : 721 – 729 .
   PubMed Web of Science ®Google Scholar
• Chrisp , P. and Clissold , S. P. 1991 . Foscarnet. A review of its antiviral activity, pharmacokinetic properties and therapeutic use in immunocompromised patients with cytomegalovirus retinitis . Drugs , 41 : 104 – 129 .
   PubMed Web of Science ®Google Scholar
• Hitchcock , M. J. , Jaffe , H. S. , Martin , J. C. and Stagg , R. J. 1996 . Cidofovir, a new agent with potent anti-herpesvirus activity . Antiviral Chem. Chemother. , 7 : 115 – 127 .
   Web of Science ®Google Scholar
• Field , A. K. and Biron , K. K. 1994 . “The end of innocence” revisited: resistance to antiviral drugs . Clin. Microbiol. Rev. , 7 : 1 – 13 .
   PubMed Web of Science ®Google Scholar
• Townsend , L. B. , Devivar , R. V. , Turk , S. T. , Nassiri , M. R. and Drach , J. C. 1995 . Design, synthesis, and antiviral activity of certain 2,5,6-trihalo-1-(β-D-ribofuranosyl)benzimidazoles . J. Med. Chem. , 38 : 4098 – 4105 .
   PubMed Web of Science ®Google Scholar
• Zou , R. , Drach , J. C. and Townsend , L. B. 1997 . 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. , 40 : 811 – 818 .
   PubMed Web of Science ®Google Scholar
• Zou , R. , Drach , J. C. and Townsend , L. B. 1997 . Design, synthesis and antiviral evaluation of 2-substituted 4,5-dichloro-and 4,6-dichloro-1-β-D-ribofuranosyIbenzimidazoles as potential agents for human cytomegalovirus infections . J. Med. Chem. , 40 : 802 – 810 .
   PubMed Web of Science ®Google Scholar
• Zou , R. , Ayres , K. R. , Drach , J. C. and Townsend , L. B. 1996 . Synthesis and antiviral activity of certain disubstituted benzimidazole ribonucleotides . J. Med. Chem. , 39 : 3477 – 3482 .
   PubMed Web of Science ®Google Scholar
• Devivar , R. V. , Kawashima , E. , Revankar , G. R. , Breitenbach , J. M. , Kreske , E. D. , Drach , J. C. and Townsend , L. B. 1994 . Benzimidazole ribonucleosides: design, synthesis, and antiviral activity of certain 2-(alkylthio)-and 2-(benzylthio)-5,6-dichloro-β-D-ribofuranosyl)benzimidazoles . J. Med. Chem , 37 : 2942 – 2948 .
   PubMed Web of Science ®Google Scholar
• Gudmundsson , K. S. , Drach , J. C. , Wotring , L. L. and Townsend , L. B. 1997 . Synthesis and antiviral activity of certain 5′-modilied analogs of 2,5,6-trichloro-1-(β-D-ribofuranosyl)benzimidazole . J. Med. Chem. , 40 : 785 – 793 .
   PubMed Web of Science ®Google Scholar
• Koszalka , G. W. , Chamberlain , S. D. , Daluge , S. M. , Boyd , F. L. , Tidwell , J. H. , Martin , M. T. , Harvey , R. J. , Frick , L. W. , Perkins , D. G. , Wang , L. H. , Drach , J. C. , Townsend , L. B. and Biron , K. K. 1996 . Benzimidazoles for the treatment of HCMV infection . XII International Roundtable: Nucleosides, Nucleotides and their Biological Application . September 15–19 1996 , La Jolla, CA. OP 41, 56
   Google Scholar
• Chamberlain , S. D. , Chan , J. H. , Tidwell , J. H. , Peckham , G. E. , Harvey , R. J. , Dornsife , R. E. , Frick , L. W. , Townsend , L. B. , Drach , J. C. and Koszalka , G. W. 1997 . Synthesis and evaluation of a series of carbohydrate modified derivatives of the anti-HCMV agent, 5,6- dichloro-2-isopropylamino-1-(β-L-ribofuranosyl)benzimidazole (1263W94) . 213th ACS National Meeting . April 13–17 1997 , San Francisco, CA. Carbohydrates, 022
   Google Scholar
• Underwood , M. R. , Harvey , R. J. , Stanat , S. C , Hemphill , M. L. , Miller , T. , Drach , J. C , Townsend , L. B. and Biron , K. K. 1998 . Inhibition of HCMV DNA maturation by a benzimidazole ribonucleoside is mediated through the UL89 gene product . J. Virol. , 72 : 717 – 725 .
   PubMed Web of Science ®Google Scholar
• Drach , J. C. , Bush , P. M. , Ptak , R. G. , Devivar , R. V. , Townsend , L. B. , Davis , M. G. , Underwood , M. R. and Biron , K. K. 1995 . Halogenated benzimidazole 5′-deoxyribonucleosides are potent and selective inhibitors of human cytomegalovirus replication . 35th Interscience Conf. Antimicrob. Agents Chemother . 1995 , San Francisco, CA.
   Google Scholar
• Guthrie , R. D. and Smith , S. C. 1968 . An improved preparation of 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose . Chem. Ind. , : 547 – 548 .
   Web of Science ®Google Scholar
• Kam , B. L. , Barascut , J.-L and Imbach , J.-L. 1979 . A general method of syntnesis and isolation, and an N.M.R.-spectroscopic study, of tetra-O-aeetyl-D-aldopentofuranoses . Carbohydr. Res. , 69 : 135 – 142 .
   Web of Science ®Google Scholar
• Hinkley , J. M. , Porcari , A. R. , Walker , J. A. L. , Swayze , E. E. and Townsend , L. B. 1998 . An improved large-scale preparation of benzimidazole-2-sulfonic acids and 2-chlorobenzimidazoles . Synth. Commun. , 28 : 1703 – 1712 .
   Web of Science ®Google Scholar
• Harrison , D. and Ralph , J. T. 1965 . Nucleophilic substitution reaction of 2-chlorobenzimidazoles. Part 1. Formation of benzimidazolin-2-ones and 2-alkoxybenzimidazoles . J. Chem. Soc. , : 236 – 239 .
   Web of Science ®Google Scholar
• Migawa , M. T. , Girardet , J.-L. , Walker , J. A. III , Koszalka , G. W. , Chamberlain , S. D. , Drach , J. C. and Townsend , L. B. 1998 . Design, synthesis, and antiviral activity of α-nucleosides: D-and L-isomers of lyxofuranosyl and 5-deoxy-lyxofuranosyl benzimidazoles . J. Med. Chem. , 41 : 1242 – 1251 .
   PubMed Web of Science ®Google Scholar
• Mizutani , K. , Kasai , R. , Nakamura , M. , Tanaka , O. and Matsuura , H. 1989 . N.M.R. spectral study of α-and β-L-arabinofuranosides . Carbohydr. Res. , 185 : 27 – 38 .
   Web of Science ®Google Scholar
• Turk , S. R. , Shipman , C. J. , Nassiri , M. R. , Genzingler , G. , Krawczyk , S. H. , Townsend , L. B. and Drach , J. C. 1987 . Pyrrolo[2,3-d]pyrimidine nucleosides as inhibitor of human cytomegalovirus . Antimicrob. Agents Chemother. , 31 : 544 – 550 .
   PubMed Web of Science ®Google Scholar
• Prichard , M. N. , Turk , S. R. , Coleman , L. A. , Engelhardt , S. L. , Shipman , C. J. and Drach , J. C. 1990 . A microtiter virus reduction assay for the evaluation of antiviral compounds against human cytomegalovirus and herpes simplex virus . J. Virol. Methods , 28 : 101 – 106 .
   PubMed Web of Science ®Google Scholar
• Prichard , M. N. and Shipman , C. J. 1990 . A three dimensional model to analyse drug-drug interactions . Antiviral Res. , 14 : 181 – 206 .
   PubMed Web of Science ®Google Scholar
• Prichard , M. N. , Prichard , L. E. , Baguley , W. A. , Nassiri , M. R. and Shipman , C. J. 1991 . Three-dimensional analysis of the synergistic cytotoxicity of ganciclovir and zidovudine . Antiviral Res. , 35 : 1060 – 1065 .
   Google Scholar