Synthesis, genotoxicity and uv-protective activity of new benzofuroxans substituted by aromatic amines

Letters in Drug Design and Discovery

Volumn 10, Issue 2, 2013, Pages 145-154

  Chugunova, Elena Alexandrovna ^b   Sazykina, Marina Alexandrovna ^c   Gibadullina, Elmira Mingaleevna ^b   Burilov, Alexander Romanovich ^b   Sazykin, Ivan Sergeevich ^c   Chistyakov, Vladimir Anatolevich ^c   Timasheva, Rezeda Eduardovna ^d   Krivolapov, Dmitry Borisovich ^b   Goumont, Regis ^a  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

^b A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

^c SOUTHERN FEDERAL UNIVERSITY   (Russian Federation)

^d KAZAN NATIONAL RESEARCH TECHNOLOGICAL UNIVERSITY   (Russian Federation)

Author keywords

Antioxidant; Benzofuroxan; Genotoxicity; Lux biosensor; SNAr; UV radiation

Indexed keywords

1,1 BIS[N (5 NITRO 6 CHLOROBENZO[1,2 C][1,2,5]OXADIAZOL 1 OXIDE 4 YL) 4 AMINOPHENYL]METHANE; 4 (4 AMINOPHENYLAMINO) 5 NITRO 6 CHLOROBENZO[1,2 C][1,2,5]OXADIAZOL 1 OXIDE; 4 ACETANISIDINE; ALPHA TOCOPHEROL; ANILINE; ANTIOXIDANT; AROMATIC AMINE; DIAMINE; N [4 (4 AMINOPHENYL)ETHYL)PHENYL] 4 AMINO 5 NITRO 6 CHLOROBENZO[1,2 C][1,2,5]OXADIAZOL 1 OXIDE; N[4 (4 AMINOPHENYL)METHYL)PHENYL] 4 AMINO 5 NITRO 6 CHLOROBENZO[1,2 C][1,2,5]OXADIAZOL 1 OXIDE; TROLOX C; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; BACTERIAL CELL; CHEMICAL INTERACTION; CONTROLLED STUDY; DRUG SYNTHESIS; GENOTOXICITY; NONHUMAN; PRIORITY JOURNAL; ULTRAVIOLET RADIATION;

EID: 84875474410     PISSN: 15701808     EISSN: 1875628X     Source Type: Journal    
DOI: 10.2174/2212797611306010007     Document Type: Article

References (38)

1. Gasco, A.; Boulton, A.J. Furoxans and Benzofuroxans. Adv. Heterocycl. Chem., 1981, 29, 251-340.
2. Katritzky, A.R.; Gordeev, M.F. Heterocyclic Rearrangements of Benzofuroxans and Related Compounds. Heterocycles, 1993, 35, 483-518.
3. Ghosh, P., Ternai, B.; Whitehouse, M. Benzofurazans and benzofuroxans: Biochemical and pharmacological properties. Med. Res. Rev. 1981, 1, 159-187.
4. Ghosh, P.; Ternai, B.; Whitehouse, M. Benzofurazans and benzofuroxans: Biochemical and pharmacological properties. Med. Res. Rev., 1981, 1, 159-187.
5. Cerecetto, H.; Porcal, W. Pharmacological properties of furoxans and benzofuroxans: recent developments. Mini-Rev. Med. Chem., 2005, 5, 57-71.
6. Cerecetto, H. and Gonzalez, M. Benzofuroxan and Furoxan. Chemistry and Biology. Top. Heterocycl. Chem., 2007, 10, 265-308.
7. Olea-Azar, C.; Rigol, C.; Mendizabal, F.; Cerecetto, H.; Di Maio, R.; González, M.; Porcal, W.; Morello, A.; Repetto, Y.; Maya, J.D. Novel benzo[1,2-c]1,2,5-oxadiazole N-oxide derivatives as antichagasic agents: chemical and biological studies. Lett. Drug. Des. Discovery, 2005, 2, 294-301.
8. Porcal, W.; Hernandez, P.; Aguirre, G.; Boiani, L.; Boiani, M.; Merlino, A.; Ferreira, A.; Di Maio, R.; Castro, A.; González, M.; Cerecetto, H. Second generation of 5-ethenylbenzofuroxan derivatives as inhibitors of Trypanosoma cruzi growth: Synthesis, biological evaluation, and structure-activity relationships. Bioorg. Med. Chem., 2007, 15, 2768-2781.
9. Jorge, S.D.; Masunari, A.; Rangel-Yagui, C.O.; Pasqualotoa, K.F.M.; Tavares, L.C. Design, synthesis, antimicrobial activity and molecular modeling studiesof novel benzofuroxan derivatives against Staphylococcus aureus. Bioorg. Med. Chem., 2009, 17, 3028-3036.
10. Medana, C.A.; Stilo, Di; Visentin, S.; Fruttero, R.; Gasco, A.; Ghigo, D.; Bosia, A. NO donor and biological properties of different benzofuroxans. Pharm. Res., 1999, 16, 956-960.
11. Hervé R.; Bernadette L. Amine, amide, sulphonamide and carbamate derivatives of benzalmalonic salts and photoprotective cosmetic composition comprised thereof. US Patent No 7326407, 2006.
12. Farng, L.O.; Horodysky A.G. Amine-containing hindered phenolic antioxidant lubricant additives and compositions thereof, US Patent No 5169547, 1978.
13. Sazykina, M.A.; Chistyakov, V.A.; Kolenko, M.A.; Azarin, K.V. Allantoin and urate as suppressors of genotoxic effect of ultraviolet radiation with wavelength 300 -400 nm. Ecological genetics, 2009, 7,44-46.
14. Macie, B.S.; Macie, L.E. The PABA story, Australas J. Dermatol, 1999, 40, 51-53.
15. Ambrosio, M. I prodotti solari, Cosmesi Dermatologica, 1992, 41, 7-41.
16. Cantrell, T.; Jussel, N.; Morris, S. Sun damage and skin protection, Pharmaceutics, 2002, 425, 1-8.
17. Zavilgelsky, G.B.; Kotova, V. Yu; Manukhov, I.V. Action of 1,1-dimethylhydrazine on bacterial cells is determined by hydrogen peroxide. Mutation Res., 2007, 634, 172-176.
18. Ptitsyn, L.R.;, Horneck, G.; Komova, O.; Kozubek, S.; Krasavin, E.A.; Bonev, M.; Rettberg, P. A biosensor for envi-ronmental genotoxin screening based on an SOS lux assay in recombinant Escherichia coli cells. Appl. Environ. Microbiol. 1997, 63, 4377-4384.
19. Frey, J.; Ghersa, P.; Palacios, P.G.; Belet, M. Physical and genetic analysis of the ColD plasmid. J. Bacteriol., 1986, 166, 15-19.
20. Timares, L.; Katiyar, S.K.; Elmets, C.A. DNA damage, apoptosis and langerhans cells - activators of UV-induced immune tolerance. Photochem. Photobiol., 2008, 84, 422-436.
21. Pfeifer, G.P.; You, Y.H.;Besaratinia, A. Mutations induced by ultraviolet light. Mutat. Res., 2005, 571(1-2),19-31.
22. Rünger, T.M.; Epe, B.; Möller, K. Processing of directly and indirectly ultraviolet-induced DNA damage in human cells. Recent Results Cancer Res., 1995, 139, 31-42.
23. Cadet, J.; Berger, M.; Douki, T.; Morin, B.; Raoul, S.; Ravanat, J.L.; Spinelli, S. Effects of UV and visible radiation on DNA-final base damage. Biol Chem., 1997, 378, 1275-1286.
24. Mouret, S.; Baudouin, C.; Charveron, M.; Favier, A.; Cadet, J.; Douki, T. Cyclobutane pyrimidine dimers are predominant DNA lesions in whole human skin exposed to UV-A radiation. Proc. Nat. Acad. Sci. USA, 2006, 103, 13765-13770.
25. Jiang, Y.; Ke, C.; Mieczkowskiy, P.A.; Marszalek, P.E. Detecting Ultraviolet Damage in Single DNA Molecules by Atomic Force Microscopy. Biophys. J. 2007, 93, 1758-1767.
26. Sheldrick, G.M. SADABS. Bruker AXS Inc, Madison, WI-53719, USA, 1997.
27. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Viterbo, D. E-map improvement in direct procedures. Acta Crystallogr. Sec. A., 1991, 47, 744-748.
28. Sheldrick, G.M. SHELX-97. Programs for crystal structure analysis Germany: University of Gottingen. 1, 2, 1997.
29. Farrugia, L.J. WinGX suite for small-molecule single-crystal crystallography. J. Appl. Crystallogr., 1999, 32, 837-838.
30. APEX2 (Version 2.1), SAINTPlus. Data Reduction and Correction Program (Version 7.31A, Bruker Advansed X-ray Solutions, BrukerAXS Inc., Madison, Wisconsin, USA, 2006.
31. Weissberger, A.; Proskauer, E.S.; Riddick, J.A.; Toops, E.E. Organic solvents. Physical properties and methods of purification. Interscience publishers, Inc. New York Interscience publishers LTD., London, 1955.
32. Burilov, A.R.; Kasymova, E.M.; Chugunova, E.A.; Yusupova, L.M.; Zobov, V.V. New benzofuroxans possessing fungicidal and bactericidal activities. RU Patent No. 228419, 2009.
33. Yusupova, L.M.; Molodykh, Z.V.; Buzykin, B.I.; Falyakhov, I.F.; Anisimova, N.N.; Sharnin, G.P.; Bulidorov, V.V.; Sviridov, S.I.; Levinson, F.S. 4-or 6-nitro-5,7-dichlorobenzofuroxan having fungicidal activity. RU Patent 2032678, 1955.
34. Maniatis, T.; Fritsch, E.F.; Sambrook, J. Molecular Cloning: a Laboratory Manual. 4th Edition Cold Spring Harbor Laboratory, New York, 1992.
35. Chistiakov, V.A.; Sazykina, M.A.; Kolenko, M.A.; Cherviakov, G.G.; Usatov, A.V. Methylene blue as a supressor of the genotoxic effect of ultraviolet radiation with a wavelength of 300-400 nm. Genetika. 2009, 45(3), 349-353.
36. Ohnaka, T. Health effects of ultraviolet radiation. Ann. Physiol. Anthropol., 1993, 12, 1-10.
37. Chugunova, E.A.; Kasymova, E.M.; Burilov, A.R.; Krivolapov, D.B.; Yusupova, L.M.; Pudovik, M.A. Reaction of dichloronitrobenzofuroxanes with amines and their derivatives. Russ. J. Gen. Chem., 2009, 79, 2207-2211.
38. Terrier, F. Nucleophilic Aromatic Displacement"; Feuer, H, Ed.; VCH: New York, 1991.