The New 1,2,3-Triazolylantracene-9,10-Diones: Synthesis and ComputerBioactivity Screening

2017;
: pp. 1 – 9
https://doi.org/10.23939/chcht11.01.001
Received: May 18, 2016
Revised: July 26, 2016
Accepted: December 12, 2017
Автори: 
Maryna Stasevych, Viktor Zvarych, Volodymyr Lunin, Mykhailo Vovk and Volodymyr Novikov

Maryna Stasevych-1, Viktor Zvarych-1, Volodymyr Lunin-1, Mykhailo Vovk-2 and Volodymyr Novikov-1

  1. Lviv Polytechnic National University, 12, Bandera St., 79013 Lviv, Ukraine; vnovikov@polynet.lviv.ua
  2. Institute of Organic Chemistry of National Academy of Sciences of Ukraine, 5, Murmanska St., 02660 Kyiv,Ukraine; mvovk@i.com.ua

The reactions of 1,4(1,5)-diazido-9,10-anthracenediones with phenylacetylene and methyl propiolate under copper(I)-catalyzed reaction of the azide-alkyne cycloaddition conditions have been studied and a series of new 1,2,3-triazole derivatives of 9,10-anthracendione have been obtained. The computer screening of synthesized compounds was carried out using the PASS Online software to identify areas of experimental biomedical researches. Compounds with high affinity to the receptors family of tyrosine kinases of the epidermal growth factor EGFR have been found among the newly synthesized 1,2,3-triazoles of 9,10-anthracenedione using molecular docking. The results of molecular docking indicate a probable mechanism for the realization of antitumor activity.

[1] Krivopalov V. and Shkurko O.: Russ. Chem. Rev., 2005, 74, 339.
[2] Agalave S., Maujan S. and Pore V.: Chem. Asian J., 2011, 6, 2696.
[3] Kolb H. and Sharpless K.: Drug Discov. Today, 2003, 8, 1128.
[4] Breinbauer R., Kohn M.: Chembiochem, 2003, 4, 1147.
[5] Tornоe C. W., Christensen C. and Meldal M.: J. Org. Chem., 2002, 67, 3057.
[6] Rostovtsev V., Green L., Fokin V. and Sharpless K.: Angew. Chem. Int. Ed., 2002, 41, 2596.
[7] Kolb H., Finn M. and Sharpless K.: Angew. Chem. Int. Ed., 2001, 40, 2004.
[8] Stasevych M., Zvarych V., Lunin V. et al.: Ind. J. Pharm. Sci., 2015, 77, 634.
[9] Stasevych M., Zvarych V., Musyanovych R. et al.: Chem. Chem. Technol., 2014, 8, 135.
[10] Zvarych V., Stasevych M., Stan’ko O. et al.: Rus. J. Org. Chem., 2014, 50, 306.
[11] Stasevych M., Zvarych V., Stan’ko O. et al.: Chem. Heterocycl. Comp., 2014, 49, 1831.
[12] Zvarych V., Stasevych M., Stan’ko O. et al.: Pharm. Chem. J., 2014, 48, 582.
[13] Hornostaev M. and Sakylydy B., Zh. Org. Khim., 1981, 17, 2217.
[14] Iden H., Fontaine F.-G. and Morin J.-F.: Org. Biomol. Chem., 2014, 12, 4117.
[15] Brass K. and Albercht F.: Chem. Ber., 1928, 61, 983.
[16] Rostovtsev V., Green L., Fokin V. and Sharpless K.: Angew. Chem. Int. Ed., 2002, 41, 2596.
[17] Fazio F., Bryan M., Blixt O. et al.: J. Am. Chem. Soc., 2002, 124, 14397.
[18] Sonogashira K., Tohda Y. and Hagihara N.: Tetrahedron Lett., 1975, 16, 4467.
[19] Wu P. and Fokin V.: Aldrichimica Acta, 2007, 40, 7.
[20] Rodionov V., Fokin V. and Finn M.: Angew. Chem. Int. Ed., 2005, 44, 2210.
[21] Lagunin A., Stepanchikova A., Filimonov D. and Poroikov V.: Bioinformatics, 2000, 16, 747.
[22] Friesner R., Murphy R., Repasky M. et al.: J. Med. Chem., 2006, 49, 6177.
[23] Berman H., Westbrook J., Feng Z. et al.: Nucleic Acids Res., 2000, 28, 235.