Identification of compounds with anti-West Nile virus activity

Journal of Medicinal Chemistry

Volumn 49, Issue 6, 2006, Pages 2127-2137

  Goodell, John R ^a   Puig Basagoiti, Francesc ^b   Forshey, Brett M ^b   Shi, Pei Yong ^b   Ferguson, David M ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b WADSWORTH CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 CHLOROPHENYLACETYL) 5 (4 NITROPHENYL) 3 (THIOPHEN 2 YL) 4,5 DIHYDRO 1H PYRAZOLE; 1 (4 CHLORPHENYLACETYL) 5 (4 NITROPHENYL) 3 (THIOPHEN 2 YL) 4,5 DIHYDRO 1H PYRAZOLE; 1 BENZOYL 5 (4 BROMOPHENYL) 3 (THIOPHEN 2 YL) 4,5 DIHYDRO 1H PYRAZOLE; 1 BENZOYL 5 (4 CHLOROPHENYL) 3 (THIOPHEN 2 YL) 4,5 DIHYDRO 1H PYRAZOLE; 1 BENZOYL 5 (4 METHOXYPHENYL) 3 (THIOPHEN 2 YL) 4,5 DIHYDRO 1H PYRAZOLE; 1 METHYL 4 (9H XANTHEN 3 YLMETHYL)PIPERAZINE; 2 (4 TERT BUTYLPHENYL) 4 (4 METHYLPIPERAZIN 1 YL)QUINOLINE; 3 (4 METHYLPIPERAZIN 1 YLMETHYL) 9H XANTHEN 9 OL; 4 (4 TERT BUTYLPHENYL) 2 (4 METHYLPIPERAZIN 1 YL)QUINOLINE; ACRIDINE DERIVATIVE; ANTIVIRUS AGENT; MYCOPHENOLIC ACID; PYRAZOLINE DERIVATIVE; QUINOLINE DERIVATIVE; RIBAVIRIN; UNCLASSIFIED DRUG; XANTHANE DERIVATIVE;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG IDENTIFICATION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; FLAVIVIRUS; HIGH THROUGHPUT SCREENING; NONHUMAN; PHYSICAL CHEMISTRY; RNA SYNTHESIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; VIRUS REPLICATION; VIRUS STRAIN; VIRUS TITRATION; WEST NILE FLAVIVIRUS;

ACRIDINES; ANIMALS; ANTIVIRAL AGENTS; CERCOPITHECUS AETHIOPS; PYRAZOLES; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP; VERO CELLS; VIRUS REPLICATION; WEST NILE VIRUS; XANTHENES;

EID: 33645402982     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm051229y     Document Type: Article

References (38)

1. Morrey, J. D.; Smee, D. F.; Sidwell, R. W.; Tseng, C. Identification of active antiviral compounds against a New York isolate of West Nile virus. Antiviral Res. 2002, 55, 107-116.
2. Crance, J. M.; Scaramozzino, N.; Jouan, A.; Garin, D. Interferon, ribavirin, 6-azauridine and glycyrrhizin: antiviral compounds active against pathogenic flaviviruses. Antiviral Res. 2003, 58, 73-79.
3. Zhang, N.; Chen, H. M.; Koch, V.; Schmitz, H.; Minczuk, M.; Stepien, P.; Fattom, A. I.; Naso, R. B.; Kalicharran, K.; Borowski, P.; Hosmane, R. S. Potent inhibition of NTPase/helicase of the West Nile virus by ring-expanded ("fat") nucleoside analogues. J. Med. Chem. 2003, 46, 4776-4789.
4. Song, G. Y.; Paul, V.; Choo, H.; Morrey, J.; Sidwell, R. W.; Schinazi, R. F.; Chu, C. K. Enantiomeric synthesis of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus. J. Med. Chem. 2001, 44, 3985-3993.
5. Mukhopadhyay, S.; Kuhn, R. J.; Rossmann, M. G. A structural perspective of the flavivirus life cycle. Nat. Rev. 2005, 3, 13-22.
6. Tilgner, M.; Deas, T. S.; Shi, P. Y. The flavivirus-conserved pentanucleotide in the 3′ stem-loop of the West Nile virus genome requires a specific sequence and structure for RNA synthesis, but not for viral replication. Virology 2005, 331, 375-386.
7. Tilgner, M.; Shi, P. Y. Structure and function of the 3′ terminal six nucleotides of the West Nile virus genome in viral replication. J. Virol. 2004, 78, 8159-8171.
8. Burke, D. S.; Monath, T. P. Flaviviruses. In Fields Virology; Knipe, D. M., Howley, P. M., Eds.; Lippincott William & Wilkins: PA, 2001; pp 1043-1126.
9. Gould, L. H.; Fikrig, E. West Nile virus: a growing concern? J. Clin. Invest. 2004, 113, 1102-1107.
10. Centers for Disease Control and Prevention. http://www.cdc.gov/ncidod/ dvbid/westnile/surv&controlCaseCount03.htm.
11. Lo, M. K.; Tilgner, M.; Bernard, K. A.; Shi, P. Y. Functional analysis of mosquito-borne flavivirus conserved sequence elements within 3′ untranslated region of West Nile virus by use of a reporting replicon that differentiates between viral translation and RNA replication. J. Virol. 2003, 77, 10004-10014.
12. Lo, M. K.; Tilgner, M.; Shi, P. Y. Potential high-throughput assay for screening inhibitors of West Nile virus replication. J. Virol. 2003, 77, 12901-12906.
13. Puig-Basagoiti, F.; Deas, T. S.; Ren, P.; Tilgner, M.; Ferguson, D. M.; et al. High-throughput assays using luciferase-expressing replicon, virus-like particle, and full-length virus for West Nile virus drug discovery. Antimicrob. Agents Chemother. 2005, 49, 4980-4988.
14. Ledizet, M.; Kar, K.; Foellmer, H. G.; Wang, T.; Bushmich, S, L.; Anderson, J. F.; Fikrig, E.; Koski, R. A. A recombinant envelope protein vaccine against West Nile virus. Vaccine 2005, 23, 3915-3924.
15. Robinson, T. P.; Ehlers, T.; Hubbard, R. B., IV; Bai, X.; Arbiser, J. L.; Goldsmith, D. J.; Bowen, J. P. Design, synthesis, and biological evaluation of angiogenesis inhibitors: aromatic enone and dienone analogues of curcumin. Bioorg. Med. Chem. Lett. 2003, 13, 115-117.
16. Bauer, U.; Egner, B. J.; Nilsson, I.; Berghult, M. Parallel solution phase synthesis of N-substituted 2-pyrazoline libraries. Tetrahedron Lett. 2001, 41, 2713-2717.
17. Pellün, R. F.; Carrasco, R.; Rodés, L.; Synthesis of N-phenylanthranilic acids using water as solvent. Synth. Commun. 1993, 23, 1447-1453.
18. Pellün, R. F.; Carrasco, R.; Millian, V.; Rodé, L. Use of pyridine as cocatalyst for the synthesis of 2-carboxy diphenyl ethers by Ullmann-Goldberg condensation. Synth. Commun. 1995, 25, 1077-1083.
19. Albert, A. The Acridines: Their Preparation, Physical, Chemical, and Biological Properties and Uses, 2nd ed.; Edward Arnold Ltd.: London, 1966.
20. Rewcastle, G. W.; Atwell, G. J.; Chambers, D.; Baguley, B. C.; Denny, W. A. Potential antitumor agents. 46. Structure-activity relationships for scridine monosubstituted derivatives of the antitumor agent N-[2-(dimethylamino)ethyl]- 9-amino-4-carboxamide. J. Med. Chem. 1986, 29, 472-477.
21. Hu, M. K.; Wu, L. J.; Hsiao, G.; Yen, M. H. Homodimeric tacrine congeners as acetylcholinesterase inhibitors. J. Med. Chem. 2002, 45, 2277-2282.
22. Varlet, D.; Fourmaintraux, E.; Depreux, P.; Lesieur, D. Synthesis of 4-[4-(N,N-dimethylsulfamoyl)piperazin-1-yl]-quinolines derivatives as sorbitol dehydrogenase potential inhibitors. Heterocycles 2003, 60, 385-396.
23. Frye, S. V.; Johnson, M. C.; Valvano, N. L. Synthesis of 2-aminobenzophenones via rapid halogen-lithium exchange in the presence of a 2-amino-N-methoxy-N-methylbenzamide. J. Org. Chem. 1991, 56, 3750-3752.
24. Croisy-Delcey, M.; Croisy, A.; Carrez, D.; Huel, C.; Chiaroni, A.; Ducrot, P.; Bisagni, E.; Jin, L.; Leclercq, G. Diphenylquinolines and isoquinolines: synthesis and primary biological evaluation. Bioorg. Med. Chem. 2000, 8, 2629-2641.
25. Hino, K.; Kawashima, K.; Oka, M.; Nagai, Y.; Uno, H.; Matsumoto, J. A novel class of antiulcer agents. 4-Phenyl-(1-piperazinyl)-quinolines. Chem. Pharm. Bull. 1989, 37, 110-115.
26. Foley, M.; Tilley, L. Quinoline antimalarials: mechanism of action and resistance and prospects for new agents. Pharmacol. Ther. 1998, 79, 55-87.
27. Deas, T. S.; Binduga-Gajewska, I.; Tilgner, M.; Ren, P.; Stein, D. A.; Moulton, H. M.; Iversen, P. L.; Kauffman, E. B.; Kramer, L. D.; Shi, P.-Y. Inhibition of flavivirus infections by antisense oligomers specifically suppressing viral translation and RNA replication. J. Virol. 2005, 4599-4609.
28. Denny, W. A. Acridine derivatives as chemotherapeutic agents. Curr. Med. Chem. 2002, 9, 1655-1665.
29. Adams, A. Crystal structures of acridines complexed with nucleic acids. Curr. Med. Chem. 2002, 9, 1667-1675.
30. Gniazdowski, M.; Denny, W. A.; Nelson, S. N.; Czyz, M. Transcription factors as targets for DNA-interacting drugs. Curr. Med. Chem. 2003, 10, 909-924.
31. Denny, W. A.; Baguley, B. C. Dual topoisomerase I/II inhibitors in cancer therapy. Curr. Top. Med. Chem. 2003, 3, 339-353.
32. George, J. W.; Ghate, S.; Matson, S. W.; Besterman, J. M. Inhibition of DNA helicase II unswinding and ATPase activities by DNA-interacting ligands. J. Biol. Chem. 1992, 267, 10683-10689.
33. Gayle, A. Y.; Baranger, A. M. Inhibition of the U1A-RNA complex by an aminoacridine derivative. Bioorg. Med. Chem. Lett. 2002, 12, 2839-2842
34. Kirk, S. R.; Luedtke, N. W.; Tor, Y. Neomycin-acridine conjugate: a potent inhibitor of Rev-RRE binding. J. Am. Chem. Soc. 2000, 122, 980-981.
35. DeJong, E. S.; Chang, C.; Gilson, M. K.; Marino, J. P. Proflavine acts as a Rev inhibitor by targeting the high-affinity Rev binding site of the Rev responsive element of HIV-1. Biochemistry 2003, 42, 8035-8046.
36. Puig-Basagoiti, F.; Tilgner, M.; Forshey, B. M.; Philpott, S. M.; Espina, N. G.; Wentworth, D. E.; Falgout, B.; Ren, P.; Ferguson, D. M.; Shi, P.-Y. A triaryl pyrazoline compound inhibits flavivirus RNA replication. Antimicrob. Agents Chemother.. in press.
37. Lo, L.; Tilgner, M.; Bernard, K.; Shi, P.-Y. Functional analysis of mosquito-borne flavivirus conserved sequence elements within 3′ untranslated region of West Nile virus using a reporting replicon that differentiates between viral translation and RNA replication. J. Virol. 2003, 77, 10004-10014.
38. Powers, D. G.; Casebier, D. S.; Fokas, D.; Ryan, W. J.; Troth, J. R.; Coffen, D. L. Automated parallel synthesis of chalcone-based screening libraries. Tetrahedron 1998, 54, 4085-96.