Synthesis and antiviral assays of some benzimidazole nucleosides and acyclonucleosides

Farmaco

Volumn 56, Issue 11, 2001, Pages 815-819

  Garuti, Laura ^a   Roberti, Marinella ^a   Gentilomi, Giovanna ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Acyclonucleosides; Antiviral assays; Benzimidazoles; Nucleosides; Synthesis

Indexed keywords

ANTIVIRUS AGENT; NUCLEOSIDE;

ARTICLE; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; ENTEROVIRUS; HELA CELL; HERPES SIMPLEX VIRUS 2; HUMAN; POLIOMYELITIS VIRUS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTIVIRAL AGENTS; CELL LINE; ENTEROVIRUS B, HUMAN; HELA CELLS; HERPESVIRUS 2, HUMAN; HUMAN; MOLECULAR STRUCTURE; NUCLEOSIDES; POLIOVIRUS; STRUCTURE-ACTIVITY RELATIONSHIP; SUPPORT, NON-U.S. GOV'T;

EID: 0035514220     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(01)01164-8     Document Type: Article

References (14)

1. L. Tamm, K. Folkers, C.H. Shunk, F.L. Horsfall, Inhibition of influenza viras multiplication by N-glycosides of benzimidazoles, J. Exp. Med. 39 (1954) 227-250.
2. A.R. Porcari, R.V. Devivar, L.S. Kucera, J.C. Drach, L.B. Townsend, Design, synthesis, and antiviral evaluation of 1-(substituted benzyl)-2-substituted-5,6-dichlorobenzimidazoles as non-nucleoside analogues of 2,5,6-trichloro-1-(β-D-ribofuranosyl)-benzimidazole, J. Med. Chem. 41 (1998) 1252-1262.
3. L.B. Townsend, R.V. Devivar, S.R. Turk, M.R. Nassiri, J.C. Drach, Design, synthesis, and antiviral activity of certain 2,5,6-trihalo-1-(β-D-ribofuranosyl)benzimidazoles, J. Med. Chem. 38 (1995) 4098-4105.
4. R. Zou, J.C. Drach, L.B. Townsend, 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. 40 (1997) 802-810.
5. Z. Zhu, B. Lippa, J.C. Drach, L.B. Townsend, Design, synthesis, and evaluation of tricyclic nucleosides (dimensional probes) as analogues of certain antiviral polyhalogenated benzimidazole ribonucleosides, J. Med. Chem. 43 (2000) 2430-2437.
6. R.V. Devivar, E. Kawashima, G.R. Revankar, J.M. Breitenbach, E.D. Kreske, J.C. Drach, L.B. Townsend, 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. 37 (1994) 2942-2949.
7. S. Saluja, R. Zhu, J.C. Drach, L.B. Townsend, Structure-activity relationships 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. 39 (1996) 881-891.
8. L. Garuti, M. Roberti, T. Rossi, C. Cermelli, M. Portolani, M. Malagoli, M. Castelli, Synthesis, antiviral and antiproliferative activity of some N-benzensulphonyl-2-(2-or 3-pyridylethyl)-benzimidazoles, Anti-Cancer Drug Des. 13 (1998) 397-406.
9. L. Garuti, M. Roberti, C. Cermelli, Synthesis and antiviral activity of some N-benzenesulphonylbenzimidazoles, Bioorg. Med. Chem. Lett. 9 (1999) 2525-2530.
10. S.C. Mauldin, C.J. Paget Jr., C. David Jones, J.M. Colacino, A.J. Baxter, K.A. Staschke, N.-G. Johansson, L. Vrang, Synthesis and antiviral activity of prodrugs of the nucleoside 1-[2′,3′-dideoxy-3′-C-(hydroxymethyl)-β-D- erythropentofuranosyl] cytosine, Bioorg. Med. Chem. 6 (1998) 577-585.
11. M.J. Robins, P.V. Hatfield, Nucleic acid related compounds. Convenient and high-yield syntheses of N-[(2-hydroxyethoxy)methyl]heterocycles as 'acyclic nucleoside' analogues, Can. J. Chem. 60 (1982) 533-547.
12. I. Pavic, A. Haltmann, A. Zimmermann, D. Michel, W. Hampl, I. Schleyer, T. Mertens, Flow cytometric analysis of herpes simplex type 1 susceptibility to acyclovir, ganciclovir and foscar-net, Antimicrob. Agents Chemother. 41 (1997) 2686-2692.
13. S. Shigeta, S. Mod, J. Watanabe, S. Soeda, K. Takahashi, T. Yamase, Synergistic antiinfluenza virus A (HINI) activities of PM-523 (polyoxometalate) and ribavirin in vitro and in vivo, Antimicrob. Agents Chemother. 41 (1997) 1423-1427.
14. G. Andrei, R. Snoeck, M. Vandeputte, E. Declercq, Activities of various compounds against murine and primate polyomaviruses, Antimicrob. Agents Chemother. 41 (1997) 587-597.