Anti-rhinovirus activity of 3-methylthio-5-aryl-4-isothiazolecarbonitrile derivatives

Antiviral Research

Volumn 45, Issue 3, 2000, Pages 199-210

  Garozzo, A ^a   Cutri C C C ^a   Castro, A ^a   Tempera, G ^a   Guerrera, F ^a   Sarva M C ^a   Geremia, E ^a  

^a UNIVERSITY OF CATANIA   (Italy)

Author keywords

Antiviral; Isothiazole derivatives; Rhinovirus

Indexed keywords

ISOTHIAZOLE DERIVATIVE;

ANTIVIRAL ACTIVITY; CARCINOMA CELL; CONTROLLED STUDY; DRUG STRUCTURE; FEMALE; HUMAN; HUMAN CELL; IC 50; PRIORITY JOURNAL; REVIEW; RHINOVIRUS;

HUMAN RHINOVIRUS 2; HUMAN RHINOVIRUS SP.; MIRIDAE; RHINOVIRUS;

EID: 0034162168     PISSN: 01663542     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-3542(00)00072-3     Document Type: Article

References (69)

1. Al-Nakib W., Tyrrell D.A.J. Drugs against rhinoviruses. J. Antimicrob. Chemother. 30:1992;115-117.
2. Al-Nakib W., Higgings P.G., Barrow G.I., Tyrrell D.A.J., Andries K., Vanden Bussche G., Taylor N., Janssen P.A.J. Suppression of colds in human volunteers challenged with rhinovirus by a new synthetic drug (R61837). Antimicrob. Agents Chemother. 33:1989;522-525.
3. Andries K. Antipicornaviral agents. Jeffries D.J., DeClercq E. Antiviral Chemotherapy. 1995;287-320 Wiley, Chichester, UK.
4. Andries K., Dewindt B., Snoeks J., Janssen P.A.J. In vitro activity of R61837, a new antirhinovirus compound. Arch. Virol. 101:1988;155-167.
5. Andries K., Dewindt B., Snoeks J., Wouters L., Moereels H., Lewi P.J., Janssen P.A.J. Two groups of rhinoviruses revealed by a panel of antiviral compounds present sequence divergence and differential pathogenicity. J. Virol. 64:1990;1117-1123.
6. Andries K., Dewindt B., Snoeks J., Willebrords R., Stokbroekx R., Lewi P.J. A comparative test of fifteen compounds against all known human rhinovirus serotypes as a basis for a more rational screening program. Antiviral Res. 16:1991;213-225.
7. Andries K., Dewindt B., Snoeks J., Willebrords R., Van Eemeren K., Stokbroekx R., Janssen P.A.J. In vitro activity of pirodavir (R77975), a substituted-phenoxy-pyridazinamine with broad-spectrum antipicornaviral activity. Antimicrob. Agents Chemother. 36:1992;100-107.
8. Arruda E., Hayden F.G. Clinical studies of antiviral agents for picornaviral infections. Jeffries D.J., DeClercq E. Antiviral Chemotherapy. 1995;321-355 Wiley, Chichester, UK.
9. Bailey T.R., Diana G.D., Kowalczyk P.J., Akullian V., Eissenstat M.A., Cutcliffe D., Mallamo J.P., Carabateas P.M., Pevear D.C. Antirhinoviral activity of heterocyclic analogs of Win 54954. J. Med. Chem. 35:1992;4628-4633.
10. Bauer D.J., Selway J.W.T., Batchelor J.F., Tisdale M., Caldwell I.C., Young D.A.B. 4′,6-Dichloroflavan (BW683C), a new antirhinovirus compound. Nature. 292:1981;369-370.
11. Castrillo J.L., Berghe V.D., Carrasco L. 3-Methylquercetin is a potent and selective inhibitor of poliovirus RNA synthesis. Virology. 152:1986;219-227.
12. Conti C., Orsi N., Stein M.L. Effect of isoflavans and isoflavenes on rhinovirus 1B and its replication in HeLa cells. Antiviral Res. 10:1988;117-127.
13. Conti C., Tomao P., Genovese D., Desideri N., Stein M.L., Orsi N. Mechanism of action of the antirhinovirus flavanoid 4′,6-dicyanoflavan. Antimicrob. Agents Chemother. 36:1992;95-99.
14. Couch R.B. Rhinoviruses. Fields B.N., Knipe D.M. Virology. 1996;713-734 Raven Press, Philadelphia, PA.
15. Cox S., Buontempo P.J., Wright-Minogue J., DeMartino J., Skelton A., Ferrari E., Schwartz J., Rozhon E., Linn C., Girijavallabhan V., O'Connell J.F. Antipicornavirus activity of SCH 47802 and analogs: in vitro and in vivo studies. Antiviral Res. 32:1996;71-79.
16. Cutrì C.C.C., Garozzo A., Siracusa M.A., Sarvà M.C., Tempera G., Geremia E., Pinizzotto M.R., Guerrera F. Synthesis and antiviral activity of a new series of 4-isothiazolecarbonitriles. Bioorg. Med. Chem. 6:1998;2271-2280.
17. Cutrì C.C.C., Garozzo A., Siracusa M.A., Sarvà M.C., Castro A., Geremia E., Pinizzotto M.R., Guerrera F. Synthesis of new 3,4,5-trisubstituted isothiazoles as effective inhibitory agents of enteroviruses. Bioorg. Med. Chem. 7:1999;225-230.
18. Denizot F., Lang R. Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J. Immunol. Methods. 89:1986;271-277.
19. Dewindt B., Van Eemeren K., Andries K. Antiviral capsid-binding compounds can inhibit the adsorption of minor receptor rhinoviruses. Antiviral Res. 25:1994;67-72.
20. Diana G.D., Salvador U.J., Zalay E.S., Carabateas P.M., Williams G.L., Collins J.C., Pancic F. Antiviral activity of some β-diketones. 2. Aryloxy alkyl diketones. In vitro activity against both RNA and DNA viruses. J. Med. Chem. 20:1977;757-761.
21. Diana G.D., McKinlay M.A., Brisson C.J., Zalay E.S., Miralles J.V., Salvador U.J. Isoxazoles with antipicornavirus activity. J. Med. Chem. 28:1985;748-752.
22. Diana G.D., Cutcliffe D., Oglesby R.C., Otto M.J., Mallamo J.P., Akullian V., McKinlay M.A. Synthesis and structure-activity studies of some disubstituted phenylisoxazoles against human picornavirus. J. Med. Chem. 32:1989;450-455.
23. Fox M.P., Otto M.J., McKinlay M.A. Prevention of rhinovirus and poliovirus uncoating by WIN 51711, a new antiviral drug. Antimicrob. Agents Chemother. 30:1986;110-116.
24. Garozzo A., Pinizzotto M.R., Furneri P.M., Baratta D., Guerrera F., Castro A., Tornetta B., Geremia E. Inhibitory effect of 3-imino-5-phenyl-3H-1,2-dithiole on poliovirus type 1 replication in vitro. Antiviral Res. 14:1990;267-278.
25. Garozzo A., Pinizzotto M.R., Guerrera F., Tempera G., Castro A., Geremia E. Antipoliovirus activity of isothiazole derivatives: mode of action of 5,5′-diphenyl-3,3′-diisothiazole disulfide (DID). Arch. Virol. 135:1994;1-11.
26. Gern J.E., Calhoun W., Swenson C., Shen G., Busse W.W. Rhinovirus infection preferentially increases lower airway responsiveness in allergic subjects. Am. J. Respir. Crit. Care Med. 155:1997;1872-1876.
27. Gwaltney J.M. Jr, Rueckert R.R. Rhinovirus. Richman D.D., Whitley R.J., Hayden F.G. Clinical Virology. 1997;1025-1047 Churchill Livingstone, New York.
28. Hayden F.G., Hipskind G.J., Woerner D.H., Eisen G.F., Janssens M., Janssen P.A., Andries K. Intranasal pirodavir (R77,975) treatment of rhinovirus colds. Antimicrob. Agents Chemother. 39:1995;290-294.
29. Hayden, F.G., Hassman, H.A., Coats, T., Menendez, R., Bock, T., 1999. Pleconaril treatment shortens duration of picornavirus respiratory illness in adults. In: Abstracts of the 39th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Francisco, CA, p. 435.
30. Ishitsuka H., Ninomiya Y.T., Ohsawa C., Fujiu M., Suhara Y. Direct and specific inactivation of rhinovirus by chalcone Ro 09-0410. Antimicrob. Agents Chemother. 22:1982;617-621.
31. Jubelt J.A., Wilson K., Ropka S.L., Guidinger P.L., McKinlay M.A. Clearance of a persistent human enterovirus infection of the mouse central nervous system by the antiviral agent disoxaril. J. Infect. Dis. 159:1989;866-871.
32. Kaiser, L., Crump, C., Patick, A.K., Zalman, L.S., Hayden, F.G., 1999. Comparative in vitro antirhinoviral activity of AG7088 and pleconaril. In: Abstracts of the 39th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Francisco, CA, p. 418.
33. Kim K.H., Willingmann P., Gong Z.X., Kremer M.J., Chapman M.S., Minor I., Oliveira M.A., Rossmann M.G., Andries K., Diana G.D., Dutko F.J., McKinlay M.A., Pevear D.C. A comparison of the anti-rhinoviral drug binding pocket in HRV14 and HRV1A. J. Mol. Biol. 230:1993;206-227.
34. Mazzei M., Balbi A., Sottofattori E., Garzoglio R., De Montis A., Corrias S., La Colla P. Synthesis of new 3,5-disubstituted isoxazoles with specific anti-group B rhinovirus activity in vitro. Eur. J. Med. Chem. 28:1993;669-674.
35. McCray J., Werner G. Production and properties of site-specific antibodies to synthetic peptide antigens related to potential cell surface receptor sites for rhinovirus. Methods Enzymol. 178:1989;676-692.
36. McKinlay M.A. Discovery and development of antipicornaviral agents. Scand. J. Infect. Dis. Suppl. 88:1993;109-115.
37. McKinlay M.A., Steinberg B.A. Oral efficacy of WIN 51711 in mice infected with human poliovirus. Antimicrob. Agents Chemother. 29:1986;30-32.
38. McKinlay M.A., Pevear D.C., Rossmann M.G. Treatment of the picornavirus common cold by inhibitors of viral uncoating and attachment. Annu. Rev. Microbiol. 46:1992;635-654.
39. McMillan J.A., Weiner L.B., Higgins A.M., Macknight K. Rhinovirus infection associated with serious illness among pediatric patients. Pediatr. Infect. Dis. J. 12:1993;321-325.
40. McSharry J.J., Caliguiri L.A., Eggers H.J. Inhibition of uncoating of poliovirus by arildone, a new antiviral drug. Virology. 97:1979;307-315.
41. Mertsola J., Ziegler T., Ruuskanen O., Vanto T., Koivikko A., Halonen P. Recurrent wheezy bronchitis and viral respiratory infections. Arch. Dis. Child. 66:1991;124-129.
42. Nicholson K.G., Kent J., Ireland D.C. Respiratory viruses and exacerbations of asthma in adults. B. M. J. 307:1993;982-986.
43. Nicholson K.G., Kent J., Hammersley V., Cancio E. Risk factors for lower respiratory complications of rhinovirus infections in elderly people living in the community: prospective cohort study. B. M. J. 313:1996;1119-1123.
44. Ninomiya Y., Shimma N., Ishitsuka H. Comparative studies on the antirhinovirus activity and the mode of action of the rhinovirus capsid binding agents, chalcone amides. Antiviral Res. 13:1990;61-74.
45. Ogata M., Matsumoto H., Shimizu S., Kida S., Wada T., Shiro M., Sato K. Synthesis and antiviral activity of sulfonamidobenzophenone oximes and sulfonamidobenzamides. J. Med. Chem. 29:1986;417-423.
46. Oren D.A., Zhang A., Nesvadba H., Rosenwirth B., Arnold E. Synthesis and activity of piperazine-containing antirhinoviral agents and crystal structure of SDZ 880-061 bound to human rhinovirus 14. J. Mol. Biol. 259:1996;120-134.
47. Otto M.J., Fox M.P., Khurt M.F., Diana G.D., McKinlay M.A. In vitro activity of WIN 51711, a new broad-spectrum antipicornavirus drug. Antimicrob. Agents Chemother. 27:1985;883-886.
48. Patick A.K., Binford S.L., Brothers M.A., Jackson R.L., Ford C.E., Diem M.D., Maldonado F., Dragovich P.S., Zhou R., Prins T.J., Fuhrman S.A., Meador J.W., Zalman L.S., Matthews D.A., Worland S.T. In vitro antiviral activity of AG7088, a potent inhibitor of human rhinovirus 3C protease. Antimicrob. Agents Chemother. 43:1999;2444-2450.
49. Pevear D.C., Fancher M.J., Felock P.J., Rossmann M.G., Miller M.S., Diana G.D., Treasurywala A.M., McKinlay M.A., Dutko F.J. Conformational change in the floor of the human rhinovirus canyon blocks adsorption to HeLa cell receptors. J. Virol. 63:1989;2002-2007.
50. Pevear D.C., Tull T.M., Seipel M.E., Groarke J.M. Activity of Pleconaril against Enteroviruses. Antimicrob. Agents Chemother. 43:1999;2109-2115.
51. Phelps D.K., Post C.B. A novel basis of capsid stabilization by antiviral compounds. J. Mol. Biol. 254:1995;544-551.
52. Pinizzotto M.R., Garozzo A., Guerrera F., Castro A., La Rosa M.G., Furneri P.M., Geremia E. In vitro antiviral activity of four isothiazole derivatives against poliovirus type 1. Antiviral Res. 19:1992;29-41.
53. Pithavala, Y.K., Hsyu, P.H., Gersten, M., Crampton, S., Penning, C.A., Daniels, R.G., Zhang, K., Paradiso, L., Kerr, B.M., 1999. Phase I evaluation of the safety and pharmacokinetics of intranasal AG7088, a novel investigational 3C protease inhibitor. In: Abstracts of the 39th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Francisco, CA, p. 418.
54. Rogers J.M., Diana G.D., McKinlay M.A. Pleconaril. A broad spectrum antipicornaviral agent. Adv. Exp. Med. Biol. 458:1999;69-76.
55. Rombaut B., Vrijsen R., Boeye A. Comparison of arildone and 3-methylquercetin as stabilizers of poliovirus. Antiviral Res. Suppl. 1:1985;67-73.
56. Rombaut B., Andries K., Boeye A. A comparison of WIN 51711 and R 78206 as stabilizers of poliovirus virions and procapsids. J. Gen. Virol. 72:1991;2153-2157.
57. Rombaut B., Andries K., Boeye A. Stabilisation of poliovirus with pirodavir. Dev. Biol. Stand. 87:1996;173-180.
58. Rosenwirth B., Oren D.A., Arnold E., Kis Z.L., Eggers H.J. SDZ 35-682, a new picornavirus capsid-binding agent with potent antiviral activity. Antiviral Res. 26:1995;65-82.
59. Rossmann M.G. The canyon hypothesis. Hiding the host cell receptor attachment site on a viral surface from immune surveillance. J. Biol. Chem. 264:1989;14587-14590.
60. Rossmann M.G., Arnold E., Erickson J.W., Frankenberger E.A., Griffith J.P., Hecht H.J., Johnson J.E., Kamer G., Luo M., Mosser A.G., Rueckert R.R., Sherry B., Vriend G. Structure of a human common cold virus and functional relationship to other picornaviruses. Nature. 317:1985;145-153.
61. Rotbart H.A., O'Connell J.F., McKinlay M.A. Treatment of human enterovirus infections. Antiviral Res. 38:1998;1-14.
62. Rozhon E., Cox S., Buontempo P., O'Connell J., Slater W., De Martino J., Schwartz J., Miller G., Arnold E., Zhang A., Morrow C., Jablonski S., Pinto P., Versace R., Duelfer T., Girijavallabhan V. SCH 38057: a picornavirus capsid-binding molecule with antiviral activity after the initial stage of viral uncoating. Antiviral Res. 21:1993;15-35.
63. Schmidt H.J., Fink R.J. Rhinovirus as a lower respiratory pathogen in infants. Pediatr. Infect. Dis. J. 10:1991;700-702.
64. Smith T.J., Kremer M.J., Luo M., Vriend G., Arnold E., Kamer G., Rossmann M.G., McKinlay M.A., Diana G.D., Otto M.J. The site of attachment in human rhinovirus 14 for antiviral agents that inhibit uncoating. Science. 233:1986;1286-1293.
65. Tisdale M., Selway J.W.T. Inhibition of an early stage of rhinovirus replication by dichloroflavan (BW683C). J. Gen. Virol. 64:1983;795-803.
66. Turner R.B., Dutko F.J., Goldstein N.H., Lockwood G., Hayden F.G. Efficacy of oral WIN 54954 for prophylaxis of experimental rhinovirus infection. Antimicrob. Agents Chemother. 37:1993;297-300.
67. Webber S.E., Tikhe J., Worland S.T., Fuhrman S.A., Hendrickson T.F., Matthews D.A., Love R.A., Patick A.K., Meador J.W., Ferre R.A., Brown E.L., DeLisle D.M., Ford C.E., Binford S.L. Design, synthesis, and evaluation of non peptidic inhibitors of human rhinovirus 3C protease. J. Med. Chem. 39:1996;5072-5082.
68. Wikel J.H., Paget C.J., DeLong D.C., Nelson J.D., Wu C.Y., Paschal J.W., Dinner A., Templeton R.J., Chaney M.O., Jones N.D., Chamberlin J.W. Synthesis of syn and anti isomers of 6-[[(hydroxyimino) phenyl] methyl]-1-[(1-methylethyl) sulfonyl]-1H-benzimidazol-amine. Inhibitors of rhinovirus multiplication. J. Med. Chem. 23:1980;368-372.
69. Woods M.G., Diana G.D., Rogge M.C., Otto M.J., Dutko F.J., McKinlay M.A. In vitro and in vivo activities of WIN 54954, a new broad-spectrum antipicornavirus drug. Antimicrob. Agents Chemother. 33:1989;2069-2074.