Search of new anticancer agent among 2,3-disubstituted 5-ylidene-1.3- thiazolidinones-4
Keywords:
synthesis, 2,3-diaryl-4-thiazolidones, l-thio-4-azaspiro[4,5]dekan-3-ones, 5-ilydene derivatives, Knoevenagel condensation, anticancer activity
Abstract
The synthetic method of difficulty accessible 5-ylidene-2,3-diaryl-4-thiazolidones was worked out base on the utilization of 2,3-diaryl-4-thiazolidones in Knovenagel condensation using potassium tert- butylat as base-catalyst. The mentioned compounds were synthesized in one-pot tricomponent reaction. The efficiency of proposed approach for synthesis of 4-substituted l-thio-4-azaspiro[4,5]dekan-3-ones and their ylidene derivatives was shown. Investigation of anticancer activity newly synthesized compounds showed that ylidene derivatives (II, IV) possessed higher activity level in comparison with their synthetic precursors (I, III).
References
1. Allen S., Newhouse B., Anderson A.S. et al. // Bioorg. Med. Chem. Let. - 2004. - Vol. 14. P. 1619-1624.
2. Alley M.C., Scudiero D.A., Monks P.A. et al. / / Cancer Research. —1988. “Vol. 48. P. 589-601.
3. Babaoglu K., Page M., Jones V. et al. // Bioorg. Med. Chem. - 2003. - Vol. 11. ó P. 3227ó3230.
4. Barreca M., Balzarini J., Chimirri A. et al. J. Med. Chem. - 2002. - Vol. 45. P. 5410-5 413.
5. Brown F.C., Jones R.S., Kent M. // Can. J. Chem. - 1963 - Vol. 41. ó P. 817ó820.
6. Boyd M.R., Paull K.D. / / Drug Development. Research. —1995. “Vol. 34. P. 91-109.
7. GreverM.R., Schepartz S.A., ChabnerB.A. // Semin. and Oncol. - 1992 - Vol. 19. ó P. 622ó638.
8. Gududuru V., Hurh E., Dalton J. et al. // Bioorg. Med. Chem. Lett. - 2004. - Vol. 14. P. 5289-5293.
9. Holmes C.P., Chinn J.P., Look G.C. et al. J. Org. Chem. - 1995 - Vol. 60. ó P. 7328ó7333.
10. Kaminskyy D., Zimenkovsky B., Lesyk R. // Eur. J. Med. Chem. - 2009. - Vol. 44. P. 3627-3636.
11. Kaminskyy D.V., Lesyk R.B. / / Biopolymers and Cell. - 2010. - Vol. 26. ó P. 136ó145.
12. Kavitha C.V., Basappa S., Swamy N. et al. // Bioor. Med. Client - 2006 - Vol. 14. - P.2290—2299.
13. Kumar A., Sharma S., Arhana R. et al. // Bioor. Med. Chem. - 2003. - Vol. 11. P. 5293-5299.
14. Lesyk R., Zimenkovsky B. // Curr. Org. Chem. - 2004. - Vol. 8. P. 1547-1578.
15. Monitor: molecules and profiles / ed. D.Tranter // Drug Descover. Tod. - 2001. - Vol. 21. P. 1127-1130.
16. Ottana R., Carotti S., Maccari R. et al. // Bioorg. Med. Chem. Let. - 2005. - Vol. 15. P. 3930-3933.
17. Prabhaka Y.S., Solomon V.R .. Gupta M.K., Katti S.B. // Topics in Heterocyclic Chemistry (QSAR and Molecular Modeling Studies in Heterocyclic Drugs II). - 2006. - Vol. 4. P. 161-249.
18. Ranjana S., Devendra P.N., Ganpat L.T. // ARKIVOC. - 2006. - Part. I. - P. 1-12.
19. Rawal R., Prabhakar Y., Katti S., Clercq E. // Bioorg. Med. Chem. - 2005. - Vol. 13. P. 6771-6776.
20. Sayyed M., Mokle S., Bokhare M. et al. // ARKIVOC. - 2006. - Part. II. - P. 187—192.
21. Shaker R.M. // Phosphor. Sulf. and Sill. - 1999. - Vol. 149 - P. 7-14.
22. Smith L, Lee T., Gould N.P., Cragoe E.J. // J. Med. Chem. - 1977 - Vol. 20. ó P. 1292ó1299.
23. Vigorita M.G, Ottana R., Monforte F. et al. // Bioorg. Med. Chem. - 2003. - Vol. 11. P. 999-1006.
2. Alley M.C., Scudiero D.A., Monks P.A. et al. / / Cancer Research. —1988. “Vol. 48. P. 589-601.
3. Babaoglu K., Page M., Jones V. et al. // Bioorg. Med. Chem. - 2003. - Vol. 11. ó P. 3227ó3230.
4. Barreca M., Balzarini J., Chimirri A. et al. J. Med. Chem. - 2002. - Vol. 45. P. 5410-5 413.
5. Brown F.C., Jones R.S., Kent M. // Can. J. Chem. - 1963 - Vol. 41. ó P. 817ó820.
6. Boyd M.R., Paull K.D. / / Drug Development. Research. —1995. “Vol. 34. P. 91-109.
7. GreverM.R., Schepartz S.A., ChabnerB.A. // Semin. and Oncol. - 1992 - Vol. 19. ó P. 622ó638.
8. Gududuru V., Hurh E., Dalton J. et al. // Bioorg. Med. Chem. Lett. - 2004. - Vol. 14. P. 5289-5293.
9. Holmes C.P., Chinn J.P., Look G.C. et al. J. Org. Chem. - 1995 - Vol. 60. ó P. 7328ó7333.
10. Kaminskyy D., Zimenkovsky B., Lesyk R. // Eur. J. Med. Chem. - 2009. - Vol. 44. P. 3627-3636.
11. Kaminskyy D.V., Lesyk R.B. / / Biopolymers and Cell. - 2010. - Vol. 26. ó P. 136ó145.
12. Kavitha C.V., Basappa S., Swamy N. et al. // Bioor. Med. Client - 2006 - Vol. 14. - P.2290—2299.
13. Kumar A., Sharma S., Arhana R. et al. // Bioor. Med. Chem. - 2003. - Vol. 11. P. 5293-5299.
14. Lesyk R., Zimenkovsky B. // Curr. Org. Chem. - 2004. - Vol. 8. P. 1547-1578.
15. Monitor: molecules and profiles / ed. D.Tranter // Drug Descover. Tod. - 2001. - Vol. 21. P. 1127-1130.
16. Ottana R., Carotti S., Maccari R. et al. // Bioorg. Med. Chem. Let. - 2005. - Vol. 15. P. 3930-3933.
17. Prabhaka Y.S., Solomon V.R .. Gupta M.K., Katti S.B. // Topics in Heterocyclic Chemistry (QSAR and Molecular Modeling Studies in Heterocyclic Drugs II). - 2006. - Vol. 4. P. 161-249.
18. Ranjana S., Devendra P.N., Ganpat L.T. // ARKIVOC. - 2006. - Part. I. - P. 1-12.
19. Rawal R., Prabhakar Y., Katti S., Clercq E. // Bioorg. Med. Chem. - 2005. - Vol. 13. P. 6771-6776.
20. Sayyed M., Mokle S., Bokhare M. et al. // ARKIVOC. - 2006. - Part. II. - P. 187—192.
21. Shaker R.M. // Phosphor. Sulf. and Sill. - 1999. - Vol. 149 - P. 7-14.
22. Smith L, Lee T., Gould N.P., Cragoe E.J. // J. Med. Chem. - 1977 - Vol. 20. ó P. 1292ó1299.
23. Vigorita M.G, Ottana R., Monforte F. et al. // Bioorg. Med. Chem. - 2003. - Vol. 11. P. 999-1006.
Published
2019-10-29
How to Cite
Kaminskyy, D., Khyluk, D., & Lesyk, R. (2019). Search of new anticancer agent among 2,3-disubstituted 5-ylidene-1.3- thiazolidinones-4. Farmatsevtychnyi Zhurnal, (6), 36-43. Retrieved from https://pharmj.org.ua/index.php/journal/article/view/744
Section
Original Articles
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