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Synthesis and pharmacological activity of 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles

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Abstract

An efficient method for the synthesis of novel 9H-imidazo[1,2-a]benzimidazole derivatives containing a biphenyl substituent at position 2 was developed. These compounds, belonging to the privileged substructures, have been tested for a wide range of pharmacological activities in the in vitro test panel. It was shown that the synthesized derivatives demonstrated high antioxidant activity, some of them inhibit type 1B protein tyrosine phosphatase, activate AMP-activated protein kinase, possess antiplatelet properties, and a rare and very interesting kind of activity, the ability to break cross-links of glycated proteins. The most active compounds can be suggested for further optimization.

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References

  1. Y. Bansal, O. Silakari, Eur. J. Med. Chem., 2014, 76,31.

    Article  CAS  Google Scholar 

  2. R. DeSimone, K. Currie, S. Mitchell, J. Darrow, D. Pippin, Comb. Chem. High Throughput Screen., 2004, 7,473.

    Article  CAS  Google Scholar 

  3. R. P. Bywater, in GPCRs: From Deorphanization to Lead Structure Identification, Ed. H. Bourne, R. Horuk, J. Kuhnke, H. Michel, Springer, Berlin, 2007, pp. 75–92.

  4. J. Kim, H. Kim, S. B. Park, J. Am. Chem. Soc., 2014, 136, 14629.

    Article  CAS  Google Scholar 

  5. D. A. Horton, G. T. Bourne, M. L. Smythe, Chem. Rev., 2003, 103,893.

    Article  CAS  Google Scholar 

  6. J. L. Izzo, Jr., A. S. Zion, J. Clin. Hypertens., 2011, 13,290.

    Article  CAS  Google Scholar 

  7. G. V. Kovalev, V. A. Anisimova, A. M. Simonov, S. M. Gofman, V. I. Petrov, I. N. Tyurenkov, Yu. K. Fomin, Pharm. Chem. J., 1979, 13,829.

    Article  Google Scholar 

  8. G. Cheng, L. Wang, W. Qu, L. Long, H. Cui, H. Liu, Y. Cao, S. Li, Acta Pharmacol. Sin., 2005, 26, 1460.

    Article  CAS  Google Scholar 

  9. O. N. Zhukovskaya, V. A. Anisimova, A. A. Spasov, P. M. Vasil´ev, V. A. Kosolapov, A. F. Kucheryavenko, N. A. Gurova, L. V. Naumenko, V. A. Kuznetsova, D. V. Sorotskii, O. A. Solov´eva, E. V. Reznikov, V. V. Gurova, V. S. Sirotenko, Pharm. Chem. J., 2016, 49,735.

    Article  CAS  Google Scholar 

  10. A. A. Spasov, P. M. Vassiliev, K. V. Lenskaya, V. A. Anisimova, T. A. Kuzmenko, A. S. Morkovnik, V. A. Kosolapov, D. A. Babkov, Pure Appl. Chem., 2017, 89, 1007.

    Article  CAS  Google Scholar 

  11. V. A. Anisimova, O. N. Zhukovskaya, A. A. Spasov, V. A. Kuznetsova, V. A. Kosolapov, D. S. Yakovlev, O. A. Solov´eva, D. V. Sorotskii, A. A. Brigadirova, E. S. Vorob´ev, Pharm. Chem. J., 2016, 49,653.

    Article  CAS  Google Scholar 

  12. O. N. Zhukovskaya, V. A. Anisimova, A. A. Spasov, D. S. Yakovlev, N. A. Gurova, A. F. Kucheryavenko, O. A. Salaznikova, V. A. Kuznetsova, D. V. Mal´tsev, A. A. Brigadirova, Ya. V. Morkovina, O. A. Solov´eva, V. V. Gurova, E. V. Reznikov, Pharm. Chem. J., 2017, 51,182.

    Article  CAS  Google Scholar 

  13. A. M. Simonov, V. A. Anisimova, Chem. Heterocycl. Compd., 1968, 4,801.

    Article  Google Scholar 

  14. V. A. Anisimova, I. E. Tolpygin, Russ. J. Org. Chem., 2011, 47, 1354.

    Article  CAS  Google Scholar 

  15. Yu. A. Zhdanov, E. A. Zvezdina, S. M. Statsenko, V. A. Anisimova, A. N. Maksimova, V. V. Korsun, Chem. Heterocycl. Compd., 1987, 23,256.

    Article  Google Scholar 

  16. R. Nagai, D. B. Murray, T. O. Metz, J. W. Baynes, Diabetes, 2012, 61,549.

    Article  CAS  Google Scholar 

  17. F. Giordanetto, D. Karis, Expert Opin. Ther. Pat., 2012, 22, 1467.

    Article  CAS  Google Scholar 

  18. D. M. Schnur, M. A. Hermsmeier, A. J. Tebben, J. Med. Chem., 2006, 49, 2000.

    Article  CAS  Google Scholar 

  19. N. E. Gel´man, E. A. Terent´yeva, T. M. Shanina, L. M. Kiparenko, Metody kolichestvennogo organicheskogo elementnogo analiza [Quantitative Organic Elemental Analysis Methods], Khimiya, Moscow, 1987 (in Russian).

    Google Scholar 

  20. A. S. Morkovnik, L. N. Divayeva, A. A. Zubenko, O. N. Podladchikova, L. N. Fetisov, A. R. Akopova, Pat. RU 2423355, Byul. isobret. [Invention Bull.], 2011, No. 9 (in Russian).

  21. A. F. Pozharskiy, V. A. Anisimova, Ye. B. Tsupak, Prakticheskiye raboty po khimii geterotsiklov [Practical Works on Heterocycle Chemistry], Rostov Univ. Publ., Rostov-on-Don, 1988, 159 pp. (in Russian).

    Google Scholar 

  22. A. A. Spasov, D. S. Yakovlev, T. M. Bukatina, A. A. Brigadirova, Bull. Exp. Biol. Med., 2014, 158,115.

    Article  CAS  Google Scholar 

  23. A. A. Spasov, D. S. Yakovlev, A. A. Brigadirova, Ros. Fiziol. Zh. im. I. M. Sechenova [I. M. Sechenov Russ. Physiol. J.], 2016, 102, 167 (in Russian).

    CAS  Google Scholar 

  24. Z. A. Gabbasov, E. G. Popov, I. Yu. Gavrilova, E. Ya. Pozin, R. A. Markosyan, Lab. delo [Lab. Work], 1989, 15 (in Russian).

    Google Scholar 

  25. W. W. D. Ratnasooriya, W. W. K. S. M. Abeysekera, T. T. B. S. T. Muthunayake, C. C. D. T. Ratnasooriya, Trop. J. Pharm. Res., 2014, 13,567.

    Article  Google Scholar 

  26. A. A. Spasov, A. I. Rashchenko, A. A. Brigadirova, Vestn. VolgGMU [Volgograd State Med. Univ. Lett.], 2016, 57, 30 (in Russian).

    Google Scholar 

  27. S. Vasan, P. Foiles, H. Founds, Arch. Biochem. Biophys., 2003, 419,89.

    Article  CAS  Google Scholar 

  28. V. Matheeussen, A.-M. Lambeir, W. Jungraithmayr, N. Gomez, K. Mc Entee, P. Van der Veken, S. Scharp, I. De Meester, Clin. Chim. Acta, 2012, 413,456.

    Article  CAS  Google Scholar 

  29. F. X. Pi-Sunyer, A. Schweizer, D. Mills, S. Dejager, Diabetes Res. Clin. Pract., 2007, 76,132.

    Article  CAS  Google Scholar 

  30. H. H. Hess, J. E. Derr, Anal. Biochem., 1975, 63,607.

    Article  CAS  Google Scholar 

  31. S. W. Suh, J. P. Bergher, C. M. Anderson, J. L. Treadway, K. Fosgerau, R. A. Swanson, J. Pharmacol. Exp. Ther., 2007, 321,45.

    Article  CAS  Google Scholar 

  32. M. Lu, P. Li, G. Bandyopadhyay, W. Lagakos, W. E. DeWolf, T. Alford, M. J. Chicarelli, L. Williams, D. A. Anderson, B. R. Baer, M. McVean, M. Conn, M. M. Veniant, P. Coward, PLoS One, 2014, 9, e88431.

    Article  Google Scholar 

  33. J. C. Pettersen, J. Litchfield, N. Neef, S. P. Schmidt, N. Shirai, K. M. Walters, B. E. Enerson, L. A. Chatman, J. A. Pfefferkorn, Toxicol. Pathol., 2014, 42,696.

    Article  Google Scholar 

  34. K. Hsiao, H. Zegzouti, J. Vidugiriene, S. A. Goueli, Promega Corp., 2015, 1.

    Google Scholar 

  35. J. M. Corton, J. G. Gillespie, S. A. Hawley, D. G. Hardie, Eur. J. Biochem., 1995, 229,558.

    Article  CAS  Google Scholar 

  36. T. Lubben, J. Clampit, M. Stashko, J. Trevillyan, M. R. Jirousek, Curr. Protoc. Pharmacol., 2001, Chapter 3, Unit 3.8.aa

    Google Scholar 

  37. M. Song, J. E. Park, S. G. Park, D. H. Lee, H. K. Choi, B. C. Park, S. E. Ryu, J. H. Kim, S. Cho, Biochem. Biophys. Res. Commun., 2009, 381,491.

    Article  CAS  Google Scholar 

  38. A. Jedsadayanmata, Naresuan Univ. J., 2005, 13,35.

    Google Scholar 

  39. P. J. Thornalley, Arch. Biochem. Biophys., 2003, 419,31.

    Article  CAS  Google Scholar 

  40. D. L. Price, P. M. Rhett, S. R. Thorpe, J. W. Baynes, J. Biol. Chem., 2001, 276, 48967.

    Article  CAS  Google Scholar 

  41. V. Z. Lankin, S. M. Gurevich, E. B. Burlakova, Trudy moskovskogo obshchestva ispytateley prirody [Transactions of the Moscow Society of Naturalists], 1975, 52, 73 (in Russian).

    CAS  Google Scholar 

  42. C. Rice-Evans, N. J. Miller, Methods Enzymol., 1994, 234,279.

    Article  CAS  Google Scholar 

  43. Yu. O. Teselkin, I. V. Babenkova, O. B. Lyubitskiy, G. I. Klebanov, Yu. A. Vladimirov, Vopr. Med. Khim. [Problems Med. Chem.], 1997, 43, 87 (in Russian).

    CAS  Google Scholar 

  44. D. J. Finney, Ann. Appl. Biol., 1949, 36, 187.

    Article  CAS  Google Scholar 

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Correspondence to A. A. Spasov or A. S. Morkovnik.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1905—1912, October, 2017.

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Spasov, A.A., Zhukovskaya, O.N., Brigadirova, A.A. et al. Synthesis and pharmacological activity of 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles. Russ Chem Bull 66, 1905–1912 (2017). https://doi.org/10.1007/s11172-017-1965-7

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  • DOI: https://doi.org/10.1007/s11172-017-1965-7

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