Skip to main navigation menu Skip to main content Skip to site footer
##common.pageHeaderLogo.altText##

Articles

Vol. 1 No. 2 (2010): April– June 2010

Design, Synthesis and Biological Evaluation of Some Dual Acting Novel Thiazolidindione Derivatives

DOI
https://doi.org/10.37285/ijddd.1.2.3
Submitted
November 19, 2024
Published
2010-05-15

Abstract

In the present study, we attempted to design and synthesize some novel dual acting 3-benzyl-5-benzylidene-thiazolidine-2,4-dione derivatives possessing antihyperglycemic as well as aldose reductase inhibitory action. The designed compounds were docked on different X-ray crystal structures of human aldose reductase 2 (ALR2) and peroxisome proliferator-activated receptor γ (PPARγ). The antihyperglycemic action of the compounds was evaluated using sucrose loaded model (SLM) and alloxan induced diabetic model (AIDM). Some of the synthesized compound demonstrated antihyperglycemic action better than that of metformin and also scores well when docked on different X-ray crystal structures of human ALR2 and were expected to be dual acting.

References

  1. [1] Wild, S.; Roglic, G.; Green, A.; Sicree, R.; King, H. Diabetes Care 2004, 27, 1047.
  2. [2] Madhavan, G.R.; Chakrabarti, R.; Reddy, K.A.; Rajesh,
  3. B. M.; Balraju, V.; Rao, P.B.; Rajagopalan, R.; Iqbal, J. Bioorg. Med. Chem. 2006, 14, 584.
  4. [3] Azukizawa, S.; Kasai, M.; Takahashi, K.; Miike, T.; Kunishiro, K.; Kanda, M.; Mukai, C.; Shirahase, H. Chem. Pharm. Bull. 2008, 56, 335.
  5. [4] Willson, T.M.; Brown, P.J.; Sternbach, D.D.; Henke, B.R.J. Med. Chem. 2000, 43, 527.
  6. [5] Kador, P.F.; Terubayashi, H.; Millen, J.; Kinoshita, J.H. The role of aldose reductase in the development of diabetic complications. In Sakamoto, N. et al. Ed., Polyol Pathway and its Role in Diabetic Complications. Elsevier Netherlands: Amsterdam, 1988; pp760.
  7. [6] Turner, A.J.; Flynn, T.G. Prog. Clin. Biol. Res. 1982, 114, 401.
  8. [7] Kador P.F. Med. Res. Rev. 1988, 8, 325.
  9. [8] Sato, S.; Kador, P.F. Biochem. Pharmacol. 1990, 40, 1033.
  10. [9] Yabe-Nishimura, C. Pharmacol. Rev. 1998, 50, 21.
  11. [10] Pingali, H.; Jain, M.; Shah, S.; Makadia, P.; Zaware, P.; Goel, A.; Patel, M.; Giri, S.; Patel, H.; Patel, P. Bioorg. Med. Chem. 2008, 16(15), 7117.
  12. [11] Rudolph, J.; Chen, L.; Majumdar, D.; Bullock, W.H.; Burns, M.; Claus, T.; Dela Cruz, F.E.; Daly, M.; Ehrgott,
  13. F. J.; Johnson, J.S.; Livingston, J.N.; Schoenleber, R.W.; Shapiro, J.; Yang, L.; Tsutsumi, M.; Ma, X. J. Med. Chem. 2007, 50, 984.
  14. [12] Caijo, F.; Mosset, P.; Grée, R.; Audinot-Bouchez, V.; Boutin, J.; Renard, P.; Caignard, D.H.; Dacquet, C.; Bioorg. Med. Chem. Lett. 2005, 15, 4421.
  15. [13] Bruno, G.; Costantino, L.; Curinga, C.; Maccari, R.; Monforte, F.; Nicolo, F.; Ottana R.; Vigoritac, M.G. Bioorg. Med. Chem. 2002, 10, 1077.
  16. [14] Sarges, R. Adv. Drug Res. 1989, 18, 139.
  17. [15] Humber, L.G. Prog. Med. Chem. 1987, 24, 299.
  18. [16] Costantino, L.; Rastelli, G.; Cignarella, G.; Vianello, P.; Barlocco, D. Exp. Opin. Ther. Pat. 1997, 7, 843.
  19. [17] Berman, H.M.; Westbrook, J.; Fenz, Z.; Gilliland, G.; Bhat, T.N.; Weissig, H.; Shindyalov, I.N.; Bourne, P.E. Nucleic Acid Res. 2000, 28, 235.
  20. [18] Zentgraf, M.; Steuber, H.; Koch, C.; La Motta, C.; Sartini, S.; Sotriffer, C.A.; Klebe, G. Angew. Chem. 2007, 46, 3575.
  21. [19] El-Kabbani, O.; Podjarny, A. Cell Mol. Life Sci. 2007, 64, 1970.
  22. [20] Steuber, H.; Zentgraf, M.; Gerlach, C.; Sotriffer, C.A.; Heine, A.; Klebe, G. J. Mol. Biol. 2006, 363, 174.
  23. [21] Van Zandt, M.C.; Jones, M.L.; Gunn, D.E.; Geraci, L.S.; Jones, J.H.; Sawicki, D.R.; Sredy, J.; Jacot, J.L.; Dicioccio, A.T.; Petrova, T.; Mitschler, A.; Podjarny,A. D. J. Med. Chem. 2005, 48, 3141.
  24. [22] Lee, Y.S.; Chen, Z.; Kador, P.F. Bioorg. Med. Chem. 1998, 6, 1811.
  25. [23] Ali, A.M.; Saber, G.E.; Mahfouz, N.M.; El-Gendy, M.A.; Radwan, A.A.; El. Hamid, M.A. Arch. Pharm. Res. 2007, 30, 1186.
  26. [24] Lo, C.P.; Shropshire, E.Y. J. Org. Chem. 1957, 22, 999.

Similar Articles

You may also start an advanced similarity search for this article.