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Synthesis of 5-(Het)arylidene-3-[2-(4-hydroxyphenyl)ethyl]-2-thioxothiazolidine-4-one Derivatives and Study of Their Antitumor and Anti-Inflammatory Activity

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Abstract

The reaction of aromatic and heteroaromatic aldehydes with 3-[2-(4-hydroxyphenyl)ethyl]-2-thioxothiazolidine-4-one was studied. A series of new 5-(het)arylidene-3[2-(4-hydroxyphenyl)ethyl]-2-thioxothiazolidine-4-ones was obtained. For synthesized compounds, antitumor and anti-inflammatory activity was studied. Hit-compounds were identified that exceeded the known comparison drugs in their action.

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REFERENCES

  1. Xu, L.L., Zheng, C.J., Sun, L.P., Miao, J., and Piao, H.R., Eur. J. Med. Chem., 2012, vol. 48, p. 174. https://doi.org/10.4172/2161-0444.1000177

    Article  CAS  PubMed  Google Scholar 

  2. Jin, X., Zheng, C.J., Song, M.X., Wu, Y., Sun, L.P., Li, Y.J., Yu, L.J, and Piao, H.R., Eur. J. Med. Chem., 2012, vol. 56, p. 203. https://doi.org/10.2174/1874842201502010040

    Article  CAS  PubMed  Google Scholar 

  3. Zimenkovskii, B.S., Kutsyk, R.V., Lesyk, R.B., Matyichuk, V.S., Obushak, N.D., and Klyufinska, T.I., Pharm. Chem. J., 2006, vol. 40, no. 6, p. 303. https://doi.org/10.1007/s11094-006-0115-6

    Article  CAS  Google Scholar 

  4. Sawaguchi, Y., Yamazaki, R., Nishiyama, Y., Sasai, T., Mae, M., Abe, A., Yaegashi, T., Nishiyama, H., and Matsuzaki, T., Anticancer Res., 2017, vol. 37, no. 8, p. 4051. https://doi.org/10.18632/oncotarget.3139

    Article  CAS  PubMed  Google Scholar 

  5. Vatolin, S., Phillips, J.G., Jha, B.K, Govindgari, S., Hu, J., Grabowski, D., Parker, Y., Lindner, D.J., Zhong, F., Distelhorst, C.W., Smith, M.R., Cotta, C., Xu, Y., Chilakala, S., Kuang, R.R., Tall, S., and Reu, F.J., Cancer Res., 2016, vol. 76, no. 11, p. 3340. https://doi.org/10.1158/0008-5472

    Article  PubMed  Google Scholar 

  6. Huang, M.J., Cheng, Y.C., Liu, C.R., Lin, S., and Liu, H.E., Exp. Hematol., 2006, vol. 34, no. 11, p. 1480. https://doi.org/10.3892/ol.2014.2277

    Article  CAS  PubMed  Google Scholar 

  7. Dago, C.D., N’ta Ambeu, C., Coulibaly, W.K., Békro, Y.A., Mamyrbekova-Bekro, J.A., Le Guével, R., Corlu, A., and Bazureau, J.P., Chem. Heterocycl. Compd., 2017, vol. 53, no. 3, p. 341. https://doi.org/10.1007/s10593-017-2056-2

    Article  CAS  Google Scholar 

  8. Song, Y., Connor, D.T., Doubleday, R., Sorenson, R.J., Sercel, A.D. Unangst, P.S., Roth, B.D., Gilbertsen, R.B., Chan, K., Schrier, D.J., Guglietta, A., Bornemeier, D.A., and Dyer, R.D., J. Med. Chem., 1999, vol. 42, p. 1151. https://doi.org/10.1021/jm9805081

    Article  CAS  PubMed  Google Scholar 

  9. El-Miligy, M.M., Hazzaa, A.A., El-Messmary, H., Nassra, R.A., and El-Hawash, S.A.M., Bioorg. Chem. Lett., 2017, vol. 72, p. 102. https://doi.org/10.1016/j.bmcl.2016.10.022

    Article  CAS  Google Scholar 

  10. Powers, J.P., Piper, D.E., Li, Y., Mayorga, V., Anzola, J., Chen, J.M., Jaen, J.C., Lee, G., Liu, J., Peterson, M.G., Tonn, G.R., Ye, O., Walker, N.P., and Wang, Z.J., J. Med. Chem., 2006, vol. 49, p. 1034. https://doi.org/10.1021/jm050859x

    Article  CAS  PubMed  Google Scholar 

  11. Lee, G., Piper, D.E., Wang, Z., Anzola, J., Powers, J., Walker, N., and Li, Y., J. Mol. Biol., 2006, vol. 357, p. 1051. https://doi.org/10.1016/j.jmb.2006.01.032

    Article  CAS  PubMed  Google Scholar 

  12. Talele, T.T., Arora, P., Kulkarni, S.S., Patel, M.R., Singh, S., Chudayeu, M., and Kaushik-Basu, N., Bioorg. Med. Chem., 2010, vol. 18, p. 4630. https://doi.org/10.1021/jm050855s

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Ramirez, M.A. and Borja, N.L., Pharmacotherap., 2008, vol. 28, p. 646. https://doi.org/10.1592/phco.28.5.646

    Article  CAS  Google Scholar 

  14. Bulic, B., Pickhardt, M., Khlistunova, I., Biernat, J., Mandelkow, E.M., Mandelkow, E., and Waldmann, H., Angew. Chem. Int. Ed., 2007, vol. 119, no. 48, p. 9375. https://doi.org/10.1002/ange.200704051

    Article  Google Scholar 

  15. Tomasic, T. and Masic, L., Curr. Med. Chem., 2009, vol. 16, no. 13, p. 1596. https://doi.org/10.2174/092986709788186200

    Article  CAS  PubMed  Google Scholar 

  16. Kaminskyy, D., Kryshchyshyn, A., and Lesyk, R., Drug. Discov., 2017, vol. 12, no. 12, p. 1233. https://doi.org/10.1080/17460441

    Article  CAS  Google Scholar 

  17. Kaminskyy, D., Kryshchyshyn, A., and Lesyk, R., Eur. J. Med. Chem., 2017, vol. 140, p. 542. https://doi.org/10.1016/j.ejmech.2017.09.031

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Pokhodylo, N., Shyyka, O., and Matiychuk, V., Med. Chem. Res., 2014, vol. 23, no. 5, p. 2426. https://doi.org/10.1007/s00044-013-0841-8

    Article  CAS  Google Scholar 

  19. Chaban, T., Klenina, O., Harkov, S., Ogurtsov, V., Chaban, I., and Nektegaev, I., Pharmacia, 2017, vol. 64, no. 4, p. 16.

    Google Scholar 

  20. Klenina, O., Chaban, T., Zimenkovsky, B., Harkov, S., Ogurtsov, V., Chaban, I., and Myrko, I., Pharmacia, 2017, vol. 64, no. 4, p. 49.

    Google Scholar 

  21. Chaban, T.I., Ogurtsov, V.V., Matiychuk, V.S., Chaban, I.G., Demchuk, I.L., and Nektegayev, I.A., Acta Chim. Slovenica, 2019, vol. 66, no. 1, p. 103. https://doi.org/10.17344/acsi.2018.4570

    Article  CAS  Google Scholar 

  22. Pokhodylo, N.T., Savka, R.D., Matiichuk, V.S., and Obushak, N.D., Russ. J. Gen. Chem., 2009, vol. 79, no. 2, p. 309. https://doi.org/10.1134/S1070363209020248

    Article  CAS  Google Scholar 

  23. Zelisko, N., Atamanyuk, D., Ostapiuk, Y., Bryhas, A., Matiychuk, V., Gzella, A., and Lesyk, R., Tetrahedron, 2015, vol. 71, no. 50, p. 9501. https://doi.org/10.1016/j.tet.2015.10.019

    Article  CAS  Google Scholar 

  24. Chaban, T., Klenina, O., Chaban, I., Ogurtsov, V., Harkov, S., and Lelyukh, M., Pharmacia, 2018, vol. 65, no. 2, p. 54.

    Google Scholar 

  25. Zubkov, F.I., Ershova, J.D., Zaytsev, V.P., Obushak, M.D., Matiychuk, V.S., Sokolova, E.A., Khrustalev, V.N., and Varlamov, A.V., Tetrahedron Lett., 2010, vol. 51, no. 52, p. 6822. https://doi.org/10.1016/j.tetlet.2010.10.046

    Article  CAS  Google Scholar 

  26. Pokhodylo, N.T., Matiychuk, V.S., and Obushak, M.D., Tetrahedron, 2009, vol. 65, no. 13, p. 2678. https://doi.org/10.1016/j.tet.2009.01.086

    Article  CAS  Google Scholar 

  27. Chaban, T.I., Klenina, O.V., Zimenkovsky, B.S., Chaban, I.G., Ogurtsov, V.V., and Shelepeten, L.S., Der Pharma Chemica, 2016, vol. 8, no. 19, p. 534.

    CAS  Google Scholar 

  28. Matiichuk, V.S., Potopnyk, M.A., and Obushak, N.D., Russ. J. Org. Chem., 2008, vol. 44, no. 9, p. 1352. https://doi.org/10.1134/S1070428008090182

    Article  CAS  Google Scholar 

  29. Chaban, T., Matiychuk, V., Ogurtsov, V., Chaban, I., Harkov, S., and Nektegaev, I., Pharmacia, 2018, vol. 65, no. 4, p. 51.

    Google Scholar 

  30. Zelisko, N., Atamanyuk, D., Vasylenko, O., Bryhas, A., Matiychuk, V., Gzella, A., and Lesyk, R., Tetrahedron, 2014, vol. 70, no. 3. Р. 720. https://doi.org/10.1016/j.tet.2013.11.083

  31. Chaban, Z., Harkov, S., Chaban, T., Klenina, O., Ogurtsov, V., and Chaban, I., Pharmacia, 2017, vol. 64, no. 3, p. 52.

    Google Scholar 

  32. Gorak, Yu.I., Obushak, N.D., Matiichuk, V.S., and Lytvyn, R.Z., Russ. J. Org. Chem., 2009, vol. 45, no. 4, p. 541. https://doi.org/10.1134/S1070428009040125

    Article  CAS  Google Scholar 

  33. Obushak, N.D., Lesyuk, A.I., Gorak, Y.I., and Matiichuk, V.S., Russ. J. Org. Chem., 2009, vol. 45, no. 9, p. 1375. https://doi.org/10.1134/S1070428009090103

    Article  CAS  Google Scholar 

  34. Obushak, N.D., Gorak, Yu.I., Matiichuk, V.S., and Lytvyn, R.Z., Russ. J. Org. Chem., 2008, vol. 44, no. 11, p. 1689. https://doi.org/10.1134/S1070428008110213

    Article  CAS  Google Scholar 

  35. Developmental Therapeutics Program. https://dtp.cancer.gov

  36. Monks, A., Scudiero, D., Skehan, P., Shoemaker, R., Paull, K., Vistica, D., Hose, C., Langley, J., Cronise, P., and Vaigro-Wolff, A.J., Nat. Cancer Inst., 1991, vol. 83, p. 757. https://doi.org/10.1093/jnci/83

    Article  CAS  Google Scholar 

  37. Boyd, M.R. and Paull, K.D., Drug Dev. Res. 1995, vol. 34, p. 91. https://doi.org/10.1002/ddr.430340203

  38. Boyd, M.R. and Teicher, B.A., Humana Press., 1997, vol. 2, p. 23. https://doi.org/10.1007/s12028-015-0160-7

    Article  Google Scholar 

  39. Shoemaker, R.H., Nature Rev. Cancer, 2006, vol. 6, p. 813. https://doi.org/10.11603/2312-0967

    Article  CAS  Google Scholar 

  40. Pillai, A.D., Rathod, P.D., Franklin, P.X., Padh, H., Vasu, K.K., and Sudarsanam, V., Biochem. Biophys. Res. Commun., 2004, vol. 317, p. 1067. https://doi.org/10.1016/j.bbrc.2004.03.148

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. Danilo Halytsky Lviv National Medical University, 79010, Lviv, Ukraine

    V. Ya. Horishny & T. I. Chaban

  2. Ivan Franko National University of Lviv, 79005, Lviv, Ukraine

    V. S. Matiychuk

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  1. V. Ya. Horishny
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Horishny, V.Y., Chaban, T.I. & Matiychuk, V.S. Synthesis of 5-(Het)arylidene-3-[2-(4-hydroxyphenyl)ethyl]-2-thioxothiazolidine-4-one Derivatives and Study of Their Antitumor and Anti-Inflammatory Activity. Russ J Gen Chem 90, 1207–1215 (2020). https://doi.org/10.1134/S1070363220070063

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