Crucial role of selenium in the virucidal activity of benzisoselenazol- 3(2h)-ones and related diselenides

Molecules

Volumn 15, Issue 11, 2010, Pages 8214-8228

  Pietka Ottlik, Magdalena ^a   Potaczek, Piotr ^a   Piasecki, Egbert ^b   Mlochowski, Jacek ^a  

^a WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

^b INSTITUTE OF IMMUNOLOGY AND EXPERIMENTAL THERAPY   (Poland)

Author keywords

Antiviral activity; Ebselen; Isoindolin 1 ones; Organoselenium compounds; Organosulfur compounds

Indexed keywords

ANTIVIRUS AGENT; EBSELEN; ORGANOSELENIUM DERIVATIVE; PYRROLE DERIVATIVE; SELENIUM; SULFUR DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; HUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE; VIRUS;

ANTIVIRAL AGENTS; AZOLES; CELL LINE, TUMOR; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORGANOSELENIUM COMPOUNDS; SELENIUM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFUR COMPOUNDS; VIRUSES;

EID: 78649474728     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15118214     Document Type: Article

References (41)

1. Mugesh, G.; du Mont, W.W.; Sies, H. Chemistry of biologically important synthetic organoselenium compounds. Chem. Rev. 2001, 101, 2125-2179.
2. Wojtowicz, H.; Chojnacka, M.; Mlochowski, J.; Palus, J.; Syper, L.; Hudecova, D.; Uher, M.; Piasecki, E.; Rybka, M. Functionalized alkyl and aryl diselenides as antimicrobial and antiviral agents: synthesis and properties. Farmaco. Sci. 2003, 58, 1235-1242.
3. Wojtowicz, H.; Kloc, K.; Maliszewska, I.; Mlochowski, J.; Pietka, M.; Piasecki, E. Azaanalogues of ebselen as antimicrobial and antiviral agents: synthesis and properties. Farmaco. Sci. 2004, 59, 863-868.
4. Pietka-Ottlik, M.; Wojtowicz-Mlochowska, H.; Kolodziejczyk, K.; Piasecki, E.; Mlochowski, J. New organoselenium compounds active against pathogenic bacteria, fungi and viruses. Chem. Pharm. Bull. (Tokyo) 2008, 56, 1423-1427.
5. Bhabak, K.P.; Mugesh, G. Amide-based glutathione peroxidase mimics: effect of secondary and tertiary amide substituents on antioxidant activity. Chem. Asian J. 2009, 4, 974-983.
6. Bhabak, K.P.; Mugesh, G. Synthesis and structure-activity correlation studies of secondary- and tertiary-amine-based glutathione peroxidase mimics. Chem. Eur. J. 2009, 15, 9846-9854.
7. Mlochowski, J.; Kloc, K.; Syper, L.; Inglot, A.D.; Piasecki, E. Aromatic and azaaromatic diselenides, benzisoselenazolones and related compounds as immunomodulators active in humans: synthesis and properties. Liebigs Ann. Chem. 1993, 1239-1244.
8. Palus, J.; Mlochowski, J.; Juchniewicz, L. 2,2′- Diselenobisbenzoates ans 2,2′-diselenobisbenzenesulfonates: new chiral aryl diselenides. Pol. J. Chem. 1998, 72, 1931-1936.
9. Kloc, K.; Mlochowski, J. Selenenylation-acylation of ketones with 2-chloroselenobenzoyl chloride. A novel route to benzo[b]selenophenes, Tetrahedron Lett. 2001, 42, 4899-4902.
10. Osajda, M.; Mlochowski, J. The reactions of 2-(chloroseleno)benzoyl chloride with nucleophiles. Tetrahedron 2002, 58, 7531-7537.
11. Honek, J.F.; Manchini, M.L.; Belleau, B. O-Chlorosulfenylbenzoyl chloride: a useful reagent in the synthesis of thioxanthones. Synth. Commun. 1983, 13, 997-984.
12. Baggaley, K.H.; English, P.D.; Jennings, J.A.; Morgan, B.; Nunn, B. Inhibitors of blood platelet aggregation. Effects of some 1,2-benzisothiazol-3- ones on platelet responsiveness to adenosine diphosphate and collagen. J. Med. Chem. 1985, 28, 1661-1667.
13. Vicini, P.; Amoretti, L.; Ballabeni, V.; Tognolini, M.; Barocelli, E. 2-Amino-Benzo[d]isothiazol- 3-one derivatives: synthesis and assessment of their antiplatelet/spasmolytic effects. Bioorg. Med. Chem. 2000, 8, 2355-2358.
14. Maggiali, C.A.; Mingiardi, M.R.; Branca C. Imidazopyrimidines with cytokinin activity. Farmaco. Sci. 1983, 38, 935-939.
15. Bordi, F.; Catellani, P.L.; Morini, G.; Plazzi, P.V.; Silva, C.; Barocelli, E.; Chiavarini, M. [4-(3- Oxo-1,2-benzisothiazolin-2-yl)alkanoic, phenyl and phenoxyalkanoic acids: synthesis and antiinflammatory, analgesic, and antipyretic properties. Farmaco. Sci. 1989, 44, 795-807.
16. Mlochowski, J.; Potaczek, P. A simple route to benzo[b]thiophenes: sulfanylation-acylation of C-H acids with 2-(chlorosulfanyl)benzoyl chloride. Phosphor. Sulfur. Silicon 2009, 184, 1115-1123.
17. Jamil, H.; Gordon, D.A.; Eustice, D.C.; Brooks, C.M.; Dickson, J.K., Jr.; Chen, Y.; Ricci, B.; Chu, C.H.; Harrity, T.W.; Ciosek, C.P.; Biller, S.A.; Gregg, R.E.; Wetterau, J.R. An inhibitor of the microsomal triglyceride transfer protein inhibits apoB secretion from HepG2 cells. Proc. Natl. Acad. Sci. USA 1996, 93, 11991-11995.
18. Guo, Z.; Shultz, A.G. Organic synthesis methodology. Preparation and diastereoselective birch reduction-alkylation of 3-substituted 2-methyl-2,3-dihydroisoindol-1-ones. J. Org. Chem. 2001, 66, 2154-2157.
19. Kreher, R.P.; Henriqe, H.; Jelitto, F.; Preut, J. Untersuchungen zur chemie von isoindolen und isoindoleninen. XXXV: 1-Alkoxy-2-alkyl-2H-isoindole - o-chinoide hetarene mit unsymmetrischer struktur. Z. Naturforsch B 1989, 44, 1132-1148.
20. Valenti, P.; Montanari, P.; Da Re, P.; Soldani, G.; Bertelli, A. Synthesis and pharmacological properties of three lidocaine cyclovinylogues. Arch. Pharm. (Weinheim) 1980, 313, 280-284.
21. Berube, D.; Lessard, J. The mechanism of electrochemical reduction of N-haloamides in acetonitrile: trapping of intermediate amide anions and father-son protonation1,2. Can. J. Chem. 1982, 60, 1127-1142.
22. Weber, R.; Renson, M. Les chlorures de chloro-3 benzisosélé nazolium-1,2: synthèse, hydrolyse, thiolation, ammonolyse. Bull. Soc. Chim. France 1976, 2, 1124-1126.
23. Mhizha, S.; Mlochowski, J. Synthesis of 2-acyl- and 2- sulfonylbenzisoselenazol-3(2H)-ones. Synth. Commun. 1997, 27, 283-292.
24. Kamigata, N.; Satoshi, H.; Michio, K.; Hiroshi, N. Photochemical ring-expansion reaction of 1,2- benzisothiazolinones. Bull. Chem. Soc. Jpn. 1985, 58, 3131-3136.
25. Correa, A.; Tellitu, I.; Dominguez, E.; SanMartin, R. Novel alternative for the N-S bond formation and its application to the synthesis of benzisothiazol-3-ones. Org. Lett. 2006, 8, 4811-4813.
26. Uchida, Y.; Kozuka, S. The thermal decomposition of N,O-diacyl-N-t- butylhydroxylamines. III. Novel routes to 2-substituted 1,2-benzoisothiazol-3- (2H)-ones. Bull. Chem. Soc. Jpn. 1982, 55, 1183-1187.
27. Kamigata, N.; Iizuka, H.; Kobayashi, M. Photochemical isomerization of 2-pyridyl- and 2-pyrazinyl-1,2-benzisothiazol-3(2H)-ones. Bull. Chem. Soc. Jpn. 1986, 59, 1601-1602.
28. Burton, D.J.; Koppes W.M. Cleavage of carboxylic acid esters to acid chlorides with dichlorotriphenylphosphorane. J. Org. Chem. 1975, 40, 3026-3032.
29. Broadus, K.M.; Kass, S.R. Benzocyclobutadienyl anion: formation and energetics of an antiaromatic molecule. J. Org. Chem. 2000, 65, 6566-6571.
30. Anderson, P.S.; Christy, M.E.; Colton, C.D.; Shepard, K.L. A useful synthesis of 3- oxodihydroisoindoles. J. Org. Chem. 1978, 43, 3719-3723.
31. Orito, K.; Horibata, A.; Nakamura, T.; Ushito, H.; Nagasaki, H.; Yuguchi, M.; Yamashita, S.; Tokuda, M. Preparation of benzolactams by Pd(OAc)2-catalyzed direct aromatic carbonylation. J. Am. Chem. Soc. 2004, 126, 14342-14343.
32. Aubert, T.; Farnier, M.; Guilard, R. Nouvelle voie de synthèse d'isoindolones et d'isoquinoléines par condensation d'iminophosphoranes avec l'ortho-phtalaldéhyde: réactions, mécanismes et étude structurale. Can. J. Chem. 1990, 68, 842-851.
33. Lessel, J. Benzodiazepine und isoindole durch acylierung von amidinen benzodiazepines and isoindoles by acylation of amidines. Pharmazie 1993, 48, 812-816.
34. Hartmann, K.H.; Troll, T. Preparation of naphthoquinone imines as nir dyes. Tetrahedron 1995, 51, 4655-4664.
35. Chapman, J.M., Jr.; Cocolas, G.H.; Hall, I.H. Hypolipidemic activity of phtalimide derivatives. 1. N-substituted phtalimide derivatives. J. Med. Chem. 1979, 22, 1399-1401.
36. Parham, J. Elaboration of bromoarylnitriles. J. Org. Chem. 1976, 41, 1187-1189.
37. Fischer, H.; Dereu, N. Mechanism of the catalytic. reduction of hydroperoxides by ebselen: A selenium - 77 NMR study. Bull. Soc. Chim. Belg. 1987, 96, 757-768.
38. Nagy, P.; Csampai, A.; Szabo, D.; Varga, J.; Harmat, V.; Ruff, F.; Kucsman, A. Structure and mechanism of hydrolysis of diaryl(acylamino)(chloro)- λ4-sulfanes and diaryl(acylamino)- sulfonium salts. J. Chem. Soc., Perkin Trans. 2001, 2, 339-349.
39. Domagala, J.M.; Bader, J.P.; Gogliotti, R.D.; Sanchez, J.P.; Stier, M.A.; Song, Y.; Prasad, J.V.; Tummino, P.J.; Scholten, J.; Harvey, P.; Holler, T.; Gracheck, S.; Hupe, D.; Rice, W.G.; Schultz, R. A new class of anti-HIV-1 agents targeted toward the nucleocapsid protein NCp7: the 2,2′- dithiobisbenzamides. Bioorg. Med. Chem. 1997, 5, 569-579.
40. Gialdi, F.; Ponci, R.; Baruffini, A. Preparation and study of the antifungal activity of o, o'-m, m'- p,p'-substituted diphenyl disulfides and the corresponding thiophenols. Farmaco. Sci. 1959, 14, 216-239.
41. Lesser, R.; Weiss, R. Über selenhaltige aromatische verbindungen. II. Chem. Ber. 1913, 46, 2640-2658.