Abstract
The review presents and summarizes comprehensive data starting from 2006 on the synthesis of mono- and di-N-oxides of 2H-benzimidazoles and their chemical properties. Especial attention was paid to the chemical transformations of 2H-benzimidazole 1,3-dioxides upon heating to give 3H-2,1,4-benzoxadiazine 4-oxides and 2H-benzimidazole mono-N-oxides. The biological activity of compounds was covered.
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Y. Bansal, O. Silakari, Bioorg. Med. Chem., 2012, 20, 6208.
L. Zhang, X.-M. Peng, G. L. V. Damu, R.-X. Geng, Ch.-H. Zhou, Med. Res. Rev., 2014, 34, 340.
M. Gaba, Ch. Mohan, Med. Chem. Res., 2016, 25, 173.
K. E. Davies, G. E. Domany, M. Farhat, J. A. Z. Herbert, A. M. Jefferson, M. A. G. Martin, H. Suschizky, J. Chem. Soc., Perkin Trans. 1, 1984, 11, 2465.
H. M. Refaat, Eur. J. Med. Chem., 2010, 45, 2949.
S. Song, J. Kim, J. Shim, J. Kim, B. H. Lee, Y. **, I. Kim, L. Kwanghee, S. Hongsuk, Sol. Energy Mater. Sol. Cells, 2012, 98, 323.
B. Iddon, Bull. Soc. Chim. Belg., 1990, 99, 673.
K. Shah, S. Chhabra, S. K. Shrivastava, P. Mishra, Med. Chem. Res., 2013, 22, 5077.
D. M. Smith, in The Chemistry of Heterocyclic Compounds, Vol.40 Part 1, Ed. P. N. Preston, J. Wiley and Sons, New York, 1981, 287.
H. Cerecetto, M. González, Mini-Rev. Med. Chem., 2008, 8, 1355.
World Health Organization, World Health Organ. Tech. Rep. Ser., 2010, 949, 1.
E. Chatelain, Comput. Struct. Biotechnol. J., 2017, 15, 98.
M. J. Haddadin, C. H. Issidores, Tetrahedron Lett., 1965, 6, 3253.
Pat. GB 1215815; https://worldwide.espacenet.com.
Pat. GB 1305138; https://worldwide.espacenet.com.
Pat. US 4343942; https://worldwide.espacenet.com.
Pat. US 4866175; https://worldwide.espacenet.com.
M. J. Abu El-Haj, J. Org. Chem., 1972, 37, 2519.
D. W. S. Latham, O. Meth-Cohn, H. Suschitzky, J. Chem. Soc., Chem. Commun., 1972, 1040.
A. B. Bulacinski, E. F. V. Screven, H. Suschitzky, Tetrahedron Lett., 1975, 41, 3577.
D. W. S. Latham, O. Meth-Cohn, H. Suschitzky, J. A. L. Herbert, J. Chem. Soc., Perkin Trans. 1, 1977, 1, 470.
J. Herbert, D. W. S. Latham, O. Meth-Cohn, H. Suschitzky, J. Chem. Soc., Chem. Commun., 1972, 1302.
H. J. Keller, I. Leichtert, G. Uhlmann, J. Weiss, Chem. Ber., 1977, 110, 1684.
L. B. Volodarskii, V. A. Samsonov, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1978, 27, 844.
V. A. Samsonov, L. B. Volodarskii, Zhurn. Org. Khimii, 1982, 18, 656 [J. Org. Chem. USSR. (Engl. Transl.), 1982, 18].
V. A. Samsonov, L. B. Volodarskii, O. Shamirzaeva, Chem. Heterocycl. Compd., 1994, 30, 460.
L. I. Khmel’nitskii, S. S. Novikov, T. I. Godovikova, Khimia Furoksanov: Reaktsii i Primenenie [Chemistry of Furoxans: Reactions and Applications], 2nd ed., Nauka, Moscow, 1996 (in Russian).
C. Bern, S. Kjos, M. J. Yabsley, S. P. Montgomery, Clin. Microbiol. Rev., 2011, 24, 655.
W. Porcal, P. Hernández, L. Boiani, M. Boiani, A. Ferreira, A. Chidichimo, J. J. Cazzulo, C. Olea-Azar, M. González, H. Cerecetto, Bioorg. Med. Chem., 2008, 16, 6995.
M. Boiani, L. Boiani, A. Denicola, S. Torres de Ortiz, E. Serna, N. Vera de Bilbao, L. Sanabria, G. Yaluff, H. Nakayama, A. Rojas de Arias, C. Vega, M. Rolan, A. Gomez-Barrio, H. Cerecetto, M. González, J. Med. Chem., 2006, 49, 3215.
M. Boiani, L. Boiani, A. Merlino, P. Hernández, A. Chidichimo, J. J. Cazzulo, H. Cerecetto, M. González, Eur. J. Med. Chem., 2009, 44, 4426.
A. Merlino, M. Boiani, H. Cerecetto, M. González, Spectrochim. Acta A, 2007, 67, 540.
A. Gerpe, L. Boiani, P. Hernandez, M. Sortino, S. Zacchino, M. Gonzalez, H. Cerecetto, Eur. J. Med. Chem., 2010, 45, 2154.
G. Álvarez, A. Gerpe, D. Benitez, F. Garibotto, S. Zacchino, C. S. Graebin, R. Gomes da Rosa, V. L. Eifler-Lima, M. González, H. Cerecetto, Lett. Drug Des. Discovery, 2010, 7, 452.
A. Merlino, D. Benitez, S. Chavez, J. Da Cunha, P. Hernández, L. W. Tinoco, N. E. Campillo, J. A. Paez, H. Cerecetto, M. González, Med. Chem. Commun., 2010, 1, 216.
A. Merlino, D. Benitez, N. E. Campillo, J. A. Páez, L. W. Tinoco, M. González, H. Cerecetto, Med. Chem. Commun., 2012, 3, 90.
V. A. Samsonov, Yu. V. Gatilov, V. A. Savel’ev, S. S. Baranova, Russ. J. Org. Chem., 2012, 48, 399.
V. A. Samsonov, Yu. V. Gatilov, V. A. Savel’ev, Russ. J. Org. Chem., 2013, 49, 1208.
E. Chugunova, V. Samsonov, T. Gerasimova, T. Rybalova, I. Bagryanskaya, Tetrahedron, 2015, 71, 7233.
N. Zhang, K. Scorsone, G. Ge, C. C. Kaffes, L. E. Dobrolecki, M. Mukherjee, M. T. Lewis, S. Berg, C. C. Stephan, D. Pati, J. Biomol. Screen., 2014, 9, 878.
Pat. WO 2015/058185 A1; https://worldwide.espacenet.com.
Pat. US 2016/0250191 A1; https://worldwide.espacenet.com.
H. T. Do, N. Zhang, D. Pati, S. R. Gilbertson, Bioorg. Med. Chem. Lett., 2016, 26, 4446.
Y. Mace, E. Bony, D. Delvaux, A. Pinto, V. Mathieu, R. Kiss, O. Feron, J. Quetin-Leclercq, O. Riant, Med. Chem. Res., 2015, 24, 3143.
E. Chugunova, V. Samsonov, N. Akylbekov, D. Mazhukin, Tetrahedron, 2017, 73, 3986.
E. A. Chugunova, N. I. Akylbekov, M. R. Gaziev, V. A. Samsonov, A. B. Dobrynin, A. R. Burilov, Russ. J. Org. Chem., 2017, 53, 1896.
J. P. Dirlam, B. W. Cue, Jr., K. J. Gombatz, J. Org. Chem., 1978, 43, 76.
K. Volkamer, H. W. Zimmermann, Chem. Ber., 1969, 102, 4177.
V. A. Samsonov, I. Yu. Bagryanskaya, Yu. V. Gatilov, V. A. Savel’ev, Russ. Chem. Bull., 2011, 60, 1723.
E. A. Chugunova, N. I. Akylbekov, N. V. Gavrilov, V. A. Samsonov, S. A. Sitnov, A. B. Dobrynin, M. A. Pudovik, A. R. Burilov, Russ. J. Gen. Chem., 2016, 86, 2548.
E. A. Chugunova, N. I. Akylbekov, V. A. Samsonov, S. A. Sitnov, A. B. Dobrynin, A. R. Burilov, Russ. J. Gen. Chem., 2017, 87, 2884.
E. A. Chugunova, N. I. Akylbekov, M. R. Gaziev, V. A. Samsonov, A. R. Burilov, Russ. J. Org. Chem., 2017, 53, 637.
G. Aguirre, M. Boiani, H. Cerecetto, A. Gerpe, M. González, Y. F. Sainz, A. Denicola, C. O. de Ocáriz, J. J. Nogal, D. Montero, J. A. Escario, Arch. Pharm. Pharm. Med. Chem., 2004, 337, 259.
Pat. US 3265706; https://worldwide.espacenet.com.
K. Blaszczak-Swiatkiewicz, M. Mirowski, K. Kaplinska, R. Kruszynski, A. Trzesowska-Kruszynska, E. Mikiciuk-Olasik, Acta Biochim. Pol., 2012, 59, 279.
G. V. Garner, H. Suschitzky, Tetrahedron Lett., 1971, 2, 169.
J. C. Hazelton, B. Iddon, A. D. Redhouse, H. Suschitzky, Tetrahedron, 1995, 51, 5597.
B. V. Glahn, W. Kramer, R. Neidlein, J. Heterocyclic Chem., 1999, 36, 1001.
M. Kaftory, V. Steiman, M. Botoshansky, Acta Crystallogr., 2002, 58, o183.
V. A. Samsonov, L. B. Volodarskii, I. Yu. Bagryanskaya, Yu. V. Gatilov, M. M. Shakirov, Chem. Heterocycl. Compd., 1995, 31, 344.
I. V. Serkov, V. V. Bezuglov, Russ. Chem. Rev., 2009, 78, 407.
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Dedicated to Academician of the Russian Academy of Sciences B. A. Trofimov on the occasion of his 80th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 1955–1970, November, 2018.
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Chugunova, E.A., Samsonov, V.A., Gazizov, A.S. et al. 2H-Benzimidazole N-oxides: synthesis, chemical properties, and biological activity. Russ Chem Bull 67, 1955–1970 (2018). https://doi.org/10.1007/s11172-018-2315-0
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DOI: https://doi.org/10.1007/s11172-018-2315-0