Antiviral properties of a series of 1,6-naphthyridine and 7,8- dihydroisoquinoline derivatives exhibiting potent activity against human cytomegalovirus

Antimicrobial Agents and Chemotherapy

Volumn 44, Issue 4, 2000, Pages 929-937

  Bedard, Jean ^a   May, Suzanne ^a   L'Heureux, Lucille ^a   Stamminger, Thomas ^b   Copsey, Alice ^c   Drach, John ^d   Huffman, John ^e   Chan, Laval ^a   Jin, Haolun ^f   Rando, Robert F ^a  

^a Shire Canada   (Canada)

^b UNIVERSITY HOSPITAL ERLANGEN   (Germany)

^c MEDICAL RESEARCH COUNCIL   (United Kingdom)

^d UNIVERSITY OF MICHIGAN   (United States)

^e UTAH STATE UNIVERSITY   (United States)

^f GILEAD SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,6 NAPHTHYRIDINE DERIVATIVE; 2 BROMO 5,6 DICHLORO 1 BETA DEXTRO RIBOFURANOSYLBENZIMIDAZOLE; 7,8 DIHYDROISOQUINOLINE DERIVATIVE; ANTIVIRUS AGENT; CIDOFOVIR; FOSCARNET; GANCICLOVIR; LUCIFERASE; UNCLASSIFIED DRUG; VIRUS ANTIGEN;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CELL GROWTH; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG MECHANISM; DRUG POTENTIATION; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN; HUMAN CELL; HUMAN CYTOMEGALOVIRUS; HUMAN RHINOVIRUS; IN VITRO STUDY; NONHUMAN; PRIORITY JOURNAL; PROMOTER REGION; VIRUS ADSORPTION; VIRUS INHIBITION;

ANTIVIRAL AGENTS; CELL LINE; CYTOMEGALOVIRUS; FLUORESCENT ANTIBODY TECHNIQUE; GANCICLOVIR; HERPESVIRUS 1, HUMAN; HERPESVIRUS 2, HUMAN; HUMANS; ISOQUINOLINES; LUCIFERASES; MICROBIAL SENSITIVITY TESTS; NAPHTHYRIDINES; TRANSFECTION;

EID: 0034065850     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.44.4.929-937.2000     Document Type: Article

References (37)

1. Baldanti, F., M. R. Underwood, S. C. Stanat, K. K. Biron, S. Chou, A. Sarasini, E. Silini, and G. Gerna. 1996. Single amino acid changes in the DNA polymerase confer foscamet resistance and slow-growth phenotype, while mutations in the UL97-encoded phosphotransferase confer ganciclovir resistance in three double-resistant human cytomegalovirus strains recovered from patients with AIDS. J. Virol. 78:1390-1395.
2. Barnard, J. A., J. H. Hoffman, R. W. Sidwell, and E. J. Reist. 1993. Selective inhibition of cytomegalovirus by 9-(3′-ethylphosphono-1′-propyloxy-methyl) guanine. Antivir. Res. 22:77-89.
3. Biron, K. K. 1991. Ganciclovir-resistant human cytomegalovirus clinical isolates: resistance mechanisms and in vitro susceptibility to antiviral agents. Transplant. Proc. 23:162-167.
4. Bruckheit, R. W., T. L. Kinjerski, V. Fliakas-Boltz, J. D. Russell, T. L. Stup, L. A. Pallansch, W. G. Brouwer, D. C. Dao, W. A. Harrison, R. J. Schultz, J. P. Bader, and S. S. Yang. 1995. Structure-activity and cross-resistance evaluations of a series of human immunodeficiency virus type 1-specific compounds related to oxathin carboxanilide. Antimicrob. Agents Chemother. 39:2718-2727.
5. Causey, D. 1991. Concomitant ganciclovir and zidovudine treatment for cytomegalovirus retinitis with HIV infection: an approach to treatment. J. Acquir. Immune Defic. Syndr. 4:S16-S21.
6. Chan, L., H. Jin, T. Stefanac, J. F. Lavallee, G. Falardean, W. Wang, J. Bedard, S. May, and L. Yuen. 1999. Discovery of the 1,6-naphthyridines as novel class of potent and selective human cytomegalovirus inhibitors. J. Med. Chem. 42:3023-3025.
7. Chan, L., H. Jin, T. Stefanac, W. Wang, J. F. Lavallee, J. Bedard, and S. May. 1999. Isoquinoline-6-carboxamides as potent and selective anti-human cytomegalovirus (HCMV) inhibitors. Bioorg. Med. Chem. Lett. 9:2583-2586.
8. Chou, S., A. Erice, M. C. Jordan, G. M. Vercellotti, K. R. Michels, C. L. Talarico, S. C. Stanat, and K. K. Biron. 1995. Analysis of the UL97 phosphotransferase coding sequence in clinical cytomegalovirus isolates and identification of mutations conferring ganciclovir resistance. J. Infect. Dis. 171:576-583.
9. Chou, S., S. Guentzel, K. R. Michel, R. C. Miner, and W. L. Drew. 1995. Frequency of UL97 phosphotransferase mutations related to ganciclovir resistance in clinical cytomegalovirus isolates. J. Infect. Dis. 172:239-242.
10. Copeland, K. F. T., P. J. McKay, and K. L. Rosenthal. 1995. Suppression of activation of the human immunodeficiency virus long terminal repeat by CD8+ Tcells is not lentivirus specific. AIDS Res. Hum. Retroviru. 11:1321-1326.
11. Drew, W. L., J. P. Lalezari, E. Glutzer, J. Flaherty, J. C. Martin, J. P. Fisher, and H. S. Jaffe. 1993. The safety, pharmacokinetics, and anti-CMV activity of weekly HPMPC in HIV positive patients excreting CMV. Antivir. Res. 20 (Suppl. 1):55.
12. Erice, A. 1999. Resistance of human cytomegalovirus to antiviral drugs. Clin. Microbiol. Rev. 12:286-297.
13. Field, A. K. 1999. Human cytomegalovirus: challenges, opportunities and new drug development. Antivir. Chem. Chemother. 10:219-232.
14. Hanson, M. H., L. C. Preheim, S. Chou, C. L. Talarico, K. K. Biron, and A. Erice. 1995. Novel mutation in the UL97 gene of a clinical cytomegalovirus strain conferring resistance to ganciclovir. Antimicroh. Agents Chemother. 39:1204-1205.
15. Hoffman, J. H., R. W. Sidwell, D. L. Barnard, A. Morrison, M. J. Otto, C. L. Hill, and R. F. Schinazi. 1997. Influenza virus-inhibitory effects of a series of germanium and silicon centred polyoxometalates. Antivir. Chem. Chemother. 8:75-83.
16. Jacobson, M. A. 1992. Review of the toxicities of foscarnet. J. Acquir. Immune Defic. Syndr. 5(Suppl.):S11-S17.
17. Jacobson, M. A. 1997. Treatment of cytomegalovirus retinitis in patients with the acquired immunodeficiency syndrome. N. Engl. J. Med. 337:105-114.
18. Jacobson, M. A., W. L. Drew, J. Feinberg, J. J. O'Donnell, P. V. Whitmore, R. D. Miner, and D. Parenti. 1991. Foscarnet therapy for ganciclovir resistant cytomegalovirus retinitis in patients with AIDS. J. Infect. Dis. 163: 1348-1351.
19. Krosky, P. M., M. N. Underwood, S. R. Turk, K. W. H. Feng, R. K. Jain, R. G. Ptark, A. C. Westerman, K. K. Biron, L. B. Townsend, and J. C. Drach. 1998. Resistance of human cytomegalovirus to henzimidazole ribonucleosides maps to two open reading frames: UL89 and UL56. J. Virol. 72:4721-4728.
20. Macher, A. M., C. M. Reichert, S. E. Straus, D. L. Longo, J. Parrillo, H. C. Lane, A. S. Fauci, A. H. Rook, J. F. Manischewitz, and G. V. J. Quinnan. 1983. Death in the AIDS patient: role of cytomegalovirus. N. Engl. J. Med. 309:1454.
21. Meyers, J. D. 1986. Infection in hone marrow transplant recipients. Am. J. Med. 81:27-38.
22. Meyers, J. D. 1991. Prevention and treatment of cytomegalovirus infection. Annu. Rev. Med. 42:179-187.
23. Ojwang, J. O., R. W. Buckneit, Y. Pommier, A. Mazumder, K. De Vreese, J. A. Este, D. Reymen, L. Pallansch, C. Lackman-Smith, T. L. Wallace, E. DeClercq, M. S. McGrath, and R. F. Rando. 1995. T30177, an oligonucleotide stabilized by an intramolecular guanosine octet, is a potent inhibitor of laboratory strains and clinical isolates of human immunodeficiency virus type 1. Antimicrob. Agents Chemother. 39:2426-2435.
24. Palestine, A. G., M. A. Polis, M. D. DeSmet, B. F. Baird, J. Falloon, J. A. Kovacs, R. T. Davey, J. J. Zurlo, K. M. Zunich, and M. Davis. 1991. A randomized, controlled trial of foscarnet in the treatment of cytomegalovirus retinitis in patients with AIDS. Appl. Microbiol. 22:797-801.
25. Prichard, M. N., L. E. Prichard, and C. Shipman. 1993. Strategic design and three-dimensional analysis of antiviral drug combinations. Antimicrob. Agents Chemother. 37:540-545.
26. Prichard, M. N., and C. Shipman, Jr. 1990. A three-dimensional model to analyze drug-drug interactions. Antivir. Res. 14:181-206.
27. Prichard, M. N., S. R. Turk, L. A. Coleman, S. L. Engelhardt, C. Shipman, Jr., and J. C. Drach. 1990. A microtiter virus yield reduction assay for the evaluation of antiviral compounds against human cytomegalovirus and herpes simplex virus. J. Virol. Methods 29:101-106.
28. Renau, T. E., J. C. Wotring, J. C. Drach, and L. B. Townsend. 1996. Synthesis of non-nucleoside analogs of toyocamycin and thiosangivamycin: influence of various 7-substituents on antiviral activity. J. Med. Chem. 39:873-880.
29. Sarasini, A., F. Baldanti, M. Furione, E. Percevalle, R. Brerra, M. Barbi, and G. Gerna. 1995. Double resistance to ganciclovir and foscarnet of four human cytomegalovirus strains recovered from AIDS patients. J. Med. Virol. 47:237-244.
30. Sidwell, R. W., and J. H. Hoffman. 1971. Use of disposable micro tissue culture plates for antiviral and interferon induction studies. Appl. Microbiol. 22:797-801.
31. Sidwell, R. W., J. H. Huffman, G. P. Khare, L. B. Allen, T. J. Witkowski, and R. K. Robins. 1972. Broad-spectrum antiviral activity of virazole: 1-D-ribofuranosyl-1,2,4-triazole-3-carboxamide. Science 177:705-706.
32. Smith, I., J. M. Cherrington, R. E. Jiles, M. D. Fuller, W. R. Freeman, and S. A. Spector. 1997. High-level resistance of cytomegalovirus to ganciclovir is associated with alterations in both the UL97 and DNA polymerase genes. J. Infect. Dis. 176:69-77.
33. Snoeck, R., G. Andrei, D. Schols, J. Balzarini, and E. De Clercq. 1998. Activity of different drug combinations against human cytomegalovirus replication in vitro. Eur. J. Clin. Microbiol. Infect. Dis. 11:1144-1155.
34. Stanat, S. C., J. E. Reardon, A. Erice, M. C. Jordan, W. L. Drew, and K. K. Biron. 1991. Ganciclovir-resistant cytomegalovirus clinical isolates: mode of resistance to ganciclovir. Antimicrob. Agents Chemother. 35:2191-2197.
35. Tatarowicz, W. A., N. S. Lurain, and K. D. Thompson. 1992. A ganciclovir-resistant clinical isolate of human cytomegalovirus exhibiting cross-resistance to other DNA polymerase inhibitors. J. Infect. Dis. 164:904-907.
36. Tyms, A. S., D. L. Taylor, and J. M. Parkin. 1989. Cytomegalovirus and the acquired immunodeficiency syndrome. J. Antimicrob. Chemother. 23:89-105.
37. Zou, R., J. C. Drach, and L. B. Townsend. 1997. Design, synthesis, and antiviral evaluation of 2-substituted 4.5-dichloro- and 4.6-dichloro-1-D-ribofuranosylbenzimidazoles as potential agents for human cytomegalovirus infections. J. Med. Chem. 40:802-810.