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Synthesis and Antimicrobial Activity of 2-[5-(R-Benzyl)-4-oxo-1,3-thiazolidin-2-ylidene]-3-oxobutanenitrile and [2-(1-Cyano-2-oxopropylidene)-4-oxo-1,3-thiazolidin-5-ylidene]acetic Acid Derivatives

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The reactions of 2-cyano-3-oxobutanethioamide with ethyl 3-aryl-2-bromopropanoates and dialkyl acetylenedicarboxylates afforded a combinatorial library of new 2-[5-(R-benzyl)-4-oxo-1,3-thtiazolidin-2-ylidene]-3-oxobutanenitrile and [2-(1-cyano-2-oxopropylidene)-4-oxo-1,3-thiazolidin-5-ylidene]acetic acid derivatives. The synthesized compounds were evaluated for antimicrobial activity, and the activity of some derivatives against gram-positive Staphylococcus aureus ATCC 43300 exceeded the activity of ceftriaxone taken as a reference drug.

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  1. Tomasić, T. and Masic, L.P., Curr. Med. Chem., 2009, vol. 16, p. 1596.

    Article  PubMed  Google Scholar 

  2. Kaminskyy, D., Kryshchyshyn, A., and Lesyk, R., Expert Opin. Drug Discovery, 2017, vol. 12, p. 1233.

    Article  CAS  Google Scholar 

  3. Kaminskyy, D., Kryshchyshyn, A., and Lesyk, R., Eur. J. Med. Chem., 2017, vol. 140, p. 542.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Jain, A.K., Vaidya, A., Ravichandran, V., Kashaw, S.K., and Agrawal, R.K., Bioorg. Med. Chem., 2012, vol. 20, p. 3378.

    Article  CAS  PubMed  Google Scholar 

  5. Sittig, M., Pharmaceutical Manufacturing Encyclopedia, Park Ridge: Noyes Publications, 1988, 2nd ed.

  6. Riham, F., Eur. J. Med. Chem., 2012, vol. 47, p. 377.

    Article  CAS  Google Scholar 

  7. Ghorab, M.M., Al-Said, M.S., and Nissan, Y.M., Arzneim. Forsch., 2012, vol. 62, p. 497.

    Article  CAS  Google Scholar 

  8. Hanna, M.M. and George, R.F., Chem. Pharm. Bull., 2012, vol. 60, p. 1195.

    Article  CAS  Google Scholar 

  9. Salem, M.A., Croat. Chem. Acta, 2017, vol. 90, p. 7.

    Article  CAS  Google Scholar 

  10. Nasr, T., Bondock, S., and Eid, S., J. Enzyme Inhib. Med. Chem., 2016, vol. 31, p. 236.

    Article  CAS  PubMed  Google Scholar 

  11. Rostom, S.A., El-Ashmawy, I.M., Abd el Razik, H.A., Badr, M.H., and Ashour, H.M., Bioorg. Med. Chem., 2009, vol. 17, p. 882.

    Article  CAS  PubMed  Google Scholar 

  12. Helal, M.H., Salem, M.A., El-Gaby, M.S., and Aljahdali, M., Eur. J. Med. Chem., 2013, vol. 65, p. 517.

    Article  CAS  PubMed  Google Scholar 

  13. 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, p. 303.

    Article  CAS  Google Scholar 

  14. Zelisko, N., Atamanyuk, D., Ostapiuk, Y., Bryhas, A., Matiychuk, V., Gzella, A., and Lesyk, R., Tetrahedron, 2015, vol. 71, p. 9501.

    Article  CAS  Google Scholar 

  15. Pokhodylo, N.T. and Matiychuk, V.S., J. Heterocycl. Chem., 2010, vol. 47, p. 415.

    Article  CAS  Google Scholar 

  16. Obushak, N.D., Gorak, Yu.I., Matiichuk, V.S., and Lytvyn, R.Z., Russ. J. Org. Chem., 2008, vol. 44, p. 1689.

    Article  CAS  Google Scholar 

  17. Pokhodylo, N.T., Matiychuk, V.S., and Obushak, N.D., Chem. Heterocycl. Compd., 2009, vol. 45, p. 121.

    Article  CAS  Google Scholar 

  18. Tupys, A., Kalembkiewicz, J., Ostapiuk, Y., Matiichuk, V., Tymoshuk, O., Woźnicka, E., and Byczyński, Ł., J. Therm. Anal. Calorim., 2017, vol. 127, p. 2233.

    Article  CAS  Google Scholar 

  19. 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, p. 6822.

    Article  CAS  Google Scholar 

  20. Pokhodylo, N.T., Savka, R.D., Matiichuk, V.S., and Obushak, N.D., Russ. J. Gen. Chem., 2009, vol. 79, p. 309.

    Article  CAS  Google Scholar 

  21. Chaban, T.I., Ogurtsov, V.V., Matiychuk, V.S., Chaban, I.G., Demchuk, I.L., and Nektegayev, I.A., Acta Chim. Slov., 2019, vol. 66, p. 103.

    Article  CAS  Google Scholar 

  22. Tsyalkovsky, V.M., Kutsyk, R.V., Matiychuk, V.S., Obushak, N.D., and Klyufinskaya, T.I., Pharm. Chem. J., 2005, vol. 39, p. 245.

    Article  CAS  Google Scholar 

  23. Hao, J., Dehlinger, V., Fivush, A.M., Rudyk, H.C., Britton, T.C., Hollinshead, S.P., Vokits, B.P., Clark, B.P., Henry, S.S., Massey, S.M., Peng, L., Dressman, B.A., Heinz, B.A., Roberts, E.F., Bracey-Walker, M.R., Swanson, S., Catlow, J.T., Love, P.L., Tepool, A.D., Peters, S.C., Simmons, R.M., Iyengar, S., McKinzie, D.L., and Monn, J.A., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 1249.

    Article  CAS  PubMed  Google Scholar 

  24. Obushak, N.D., Matiichuk, V.S., and Ganushchak, N.I., Russ. J. Org. Chem., 1998, vol. 34, p. 239.

    CAS  Google Scholar 

  25. Obushak, N.D., Lesyuk, A.I., Gorak, Y.I., and Matiichuk, V.S., Russ. J. Org. Chem., 2009, vol. 45, p. 1375.

    Article  CAS  Google Scholar 

  26. Obushak, N.D., Lesyuk, A.I., Gorak, Y.I., and Matiichuk, V.S., Russ. J. Org. Chem., 2009, vol. 45, p. 1375.

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Correspondence to V. S. Matiichuk.

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Horishny, V.Y., Matiichuk, V.S. Synthesis and Antimicrobial Activity of 2-[5-(R-Benzyl)-4-oxo-1,3-thiazolidin-2-ylidene]-3-oxobutanenitrile and [2-(1-Cyano-2-oxopropylidene)-4-oxo-1,3-thiazolidin-5-ylidene]acetic Acid Derivatives. Russ J Org Chem 56, 1557–1561 (2020).

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