Synthesis and studying of antituberculosis activity of 5-arylidene-3-(benzothizol-2-ylamino)-2-thюхо-4- thiazolidones

  • L.M. Mosula -
  • R.B. Lesyk -
Keywords: synthesis, 2-thioxo-4-thiazolidones, Knoevenagel reaction, antituberculosis activity

Abstract

Following reaction of 2-hydrazinobenzthiazole and thiocarbonyl-bis-thioglicolic acid 3-(benzothiazol- 2-ylamino)-2-thioxo-4-thiazolidone was synthesized as starting compound for obtaining of new 5-ary- lidenederivatives in Knoevenagel condensation with aromatic aldehydes. Synthesized compounds displayed hydrazine-hydrazono tautomerism, which confirmed by NMR spectra. Antituberculosis activity screening allowed us to identify 5-phenylpropenylidene- and 5-(4-tret-butylphenylmethylidene)-3-(benzothiazol- 2-ylamino)-2-thioxo-4-thiazolidones as «hit-compounds», which are treated as a platform for novel directions for the purposeful synthesis of new molecules with «drug-like» properties.

References

Zimenkovsky BS, Dog RB 4-Thiazolidones. Chemistry, physiological action, prospects. - Vinnytsia: New book, 2004. - 106 p.

Popov-Pergal K., Chekovich J .. Pergal M. // JOH. - 1994. - T. 61, № 9. - S. 2112—2116.

Roman OM, Nektegaev IO, Horishniy VY, Lesyk RB // Pharmac. magazine. —2002. - № 3. - P. 56—59.

Babaoglu K., Page MA, Jones V.C. // Bioorg. Med. Chem. Lett. - 2003. - Vol. 13. ó P. 3227ó3230.

Brooke E.W., Davies S.G., Mulvaney A.W. // Bioorg. Med. Chem. Lett. - 2003. - Vol. 13. ó P. 2527ó2530.

Carlson E.E., May J.F., Kiessling L.L. // Chemistry & Biology. - 2006. - Vol. 13. ó P. 825ó837.

Carter P.H., Scherle P.A., Muckelbauer J.A. et al. // Proc. Natl. Acad. Sci. U.S.A. - 2001. - Vol. 98. P. 11879-11884.

Collins L.A., Franzblau S.G. // Antimicrob. Agents Chemother. - 1997. - Vol. 41. ó P. 1004ó1009.

Gvozdjokova A., Ivanovicova H. // Chem, Papers. - 1986. - Vol. 40, № 6. ó P. 797ó800.

Janin Y.L. // Bioorg. Med. Chem. - 2005. - Vol. 15. ó P. 2479ó2513

Lesyk R., Vladzimirska O., Holota S. et al, // Eur. J. Med. Chem. - 2007. - Vol. 42. ó P. 641ó648.

Lesyk R., Zimenkovsky V. // Current Organic Chemistry. - 2004. - Vol 8, № 16. - P. 1547—1578.

Lesyk R., Zimenkovsky B., Lukyanchuk V. et al. // Annales of the Polish Chemical Society. - 2003. - Vol. 2, part I. - P. 293-298.

Liu W., Bulgaru A., Haigentz M. et al. // Curr. Med. Chem .: Anti-Cancer Agents. - 2003. - Vol. 3. - P. 217-223.

Mahran A., El-Nasry S.M.F., Allam S.R. et al. // Pharmazie. - 2003. - Vol. 58. —P. 527—530.

Maymona K. 11 Phosphorus, Sulfur and Silicon and Related Elements. - 1992. —Vol. 71, № 1—4. - P. 212-223.

Nektegayev I., Lesyk R. // Sci. Pharm. - 1999. - Vol. 67. ó P. 227ó230.

Singh T., Srivastava VK, Saxena KK. et al. // Arch. Pharm. Chem. Sci. - 2006. - Vol. 339. ó P. 466ó472.

Theocharis S., Margeli, A., Kouraklis G. et al. // Curr. Med. Chem .: Anti-Cancer Agents. - 2003. - Vol. 3. - P. 239-251.

Zimenkovsky B., Kazmirchuk G., Zaprutko L. et al. // Annales of the Polish Chemical Society. - 2005. - Vol. 1. - P. 69-72.

Yoshida M., Hayakawa M., Hayashy N. et al. The Bioorg. Med. Chem. Lett. - 2005. - Vol. 58. P. 527-530.

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Published
2008-02-20
How to Cite
Mosula, L., & Lesyk, R. (2008). Synthesis and studying of antituberculosis activity of 5-arylidene-3-(benzothizol-2-ylamino)-2-thюхо-4- thiazolidones. Farmatsevtychnyi Zhurnal, (1), 56-61. Retrieved from https://pharmj.org.ua/index.php/journal/article/view/1211
Section
Original Articles

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