Synthesis, characterization and antiglaucoma activity of some novel pyrazole derivatives of 5-amino-1,3,4-thiadiazole-2-sulfonamide

European Journal of Medicinal Chemistry

Volumn 45, Issue 11, 2010, Pages 4769-4773

  Kasmoullar, Rahmi ^a   Bülbül, Metin ^a   Arslan, B Sekin ^a   Göke, Baak ^a  

^a DUMLUPINAR UNIVERSITY   (Turkey)

Author keywords

1,3,4 Thiadiazole 2 sulfonamide; Carbonic anhydrase; Glaucoma; Inhibition; Pyrazole

Indexed keywords

5 AMINO 1,3,4 THIADIAZOLE 2 SULFONAMIDE; ANTIGLAUCOMA AGENT; BENZENESULFONAMIDE DERIVATIVE; CARBONATE DEHYDRATASE; DIETHYL 2 [2 [3 [4 (ETHOXYCARBONYL) 5 PHENYL 3 (5 SULFAMOYL 1,3,4 THIADIAZOL 2 YLCARBAMOYL) 1H PYRAZOL 1 YL]PHENYL]HYDRAZONO]MALONATE; ESTERASE; ETHYL 1 (2 METHYL 1 (2 OXOPROPYL) 1H INDOL 4 YL] 5 PHENYL 3 (5 SULFAMOYL 1,3,4 THIADIAZOL 2 YLCARBAMOYL) 1H PYRAZOLE 4 CARBOXYLATE; ETHYL 1 (3 IODOPHENYL) 5 PHENYL 3 (5 SULFAMOYL 1,3,4 THIADIAZOL 2 YLCARBAMOYL) 1H PYRAZOLE 4 CARBOXYLATE; ETHYL 1 [3 [(2 HYDROXYNAPHTHALEN 1 YL)DIAZENYL]PHENYL] 5 PHENYL 3 (5 SULFAMOYL 1,3,4 THIADIAZOL 2 YLCARBAMOYL) 1H PYRAZOLE 4 CARBOXYLATE; ETHYL 1 [3 [(4 HYDROXYPHENYL)DIAZENYL]PHENYL] 5 PHENYL 3 (5 SULFAMOYL 1,3,4 THIADIAZOL 2 YLCARBAMOYL) 1H PYRAZOLE 4 CARBOXYLATE; ETHYL 1 [3 [2 (1 ETHOXY 1,3 DIOXO3 PHENYLPROPAN 2 YLIDENE)HYDRAZINYL]PHENYL] 5 PHENYL 3 (5 SULFAMOYL 1,3,4 THIADIAZOL 2 YLCARBAMOYL) 1H PYRAZOLE 4 CARBOXYLATE; ETHYL 1 [3 [2 (1 ETHOXY 1,3 DIOXOBUTAN 2 YLIDENE)HYDRAZINYL]PHENYL] 5 PHENYL 3 (5 SULFAMOYL 1,3,4 THIADIAZOL 2 YLCARBAMOYL) 1H PYRAZOLE 4 CARBOXYLATE; ETHYL 1 [3 [2 (1 TERT BUTOXY 1,3 DIOXOBUTAN 2 YLIDENE)HYDRAZINYL]PHENYL] 5 PHENYL 3 (5 SULFAMOYL 1,3,4 THIADIAZOL 2 YLCARBAMOYL) 1H PYRAZOLE 4 CARBOXYLATE; ETHYL 1 [3 [2 (1,3 DIOXO 1 PHENYLBUTAN 2 YLIDENE)HYDRAZINYL]PHENYL] 5 PHENYL 3 (5 SULFAMOYL 1,3,4 THIADIAZOL 2 YLCARBAMOYL) 1H PYRAZOLE 4 CARBOXYLATE; ETHYL 1 [3 [2 (1,3 DIOXO 1,3 DIPHENYLPROPAN 2 YLIDENE)HYDRAZINYL]PHENYL] 5 PHENYL 3 (5 SULFAMOYL 1,3,4 THIADIAZOL 2 YLCARBAMOYL) 1H PYRAZOLE 4 CARBOXYLATE; ETHYL 1 [3 [2 (2,4 DIOXOPENTAN 3 YLIDENE)HYDRAZINYL]PHENYL] 5 PHENYL 3 (5 SULFAMOYL 1,3,4 THIADIAZOL 2 YLCARBAMOYL) 1H PYRAZOLE 4 CARBOXYLATE; HYDROLYASE; ISOENZYME; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; IC 50;

CARBONIC ANHYDRASE INHIBITORS; GLAUCOMA; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; SULFONAMIDES;

EID: 77957833394     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.07.041     Document Type: Article

References (37)

1. C.T. Supuran Nat. Rev. Drug Discov. 7 2008 168 181
2. M. Bülbül, N. Saraolu, Ö.. Küfreviolu, and M. ifti Bioorg. Med. Chem. 10 2002 2561 2567
3. M. Bülbül, R. Kasmoullar, and Ö.. Küfreviolu J. Enz. Inhib. Med. Chem. 23 2008 895 900
4. Ö Özensoy, F. Kockar, O. Arslan, S. Isk, C.T. Supuran, and M. Lyon Clin. Biochem. 39 2006 804 809
5. C.T. Supuran, F. Mincione, A. Scozzafava, F. Briganti, G. Mincione, and M.A. Ilies Eur. J. Med. Chem. 33 1998 247 254
6. V.K. Agrawal, M. Banerji, M. Gupta, J. Singh, P.V. Khadikar, and C.T. Supuran Eur. J. Med. Chem. 40 2005 1002 1012
7. A. Thiry, S. Rolin, D. Vullo, A. Frankart, A. Scozzafava, J.-M. Dogne, J. Wouters, C.T. Supuran, and B. Masereel Eur. J. Med. Chem. 43 2008 2853 2860
8. A. Thiry, A. Delayen, L. Goossens, R. Houssin, M. Ledecq, A. Frankart, J.-M. Dogne, J. Wouters, C.T. Supuran, J.-P. Hénichart, and B. Masereel Eur. J. Med. Chem. 44 2009 511 518
9. J.Y. Winum, A. Thiry, K.E. Cheikh, J.M. Dogné, J.L. Montero, D. Vullo, A. Scozzafava, B. Masereel, and C.T. Supuran Bioorg. Med. Chem. Lett. 17 2007 2685 2691
10. A. Scozzafava, M.D. Banciu, A. Popescu, and C.T. Supuran J. Enz. Inhib. Med. Chem. 15 2000 443 453
11. J.S. Schuman Clin. Therap. 22 2000 167 208
12. B.L. Wilkinson, L.F. Bornaghi, T.A. Houston, A. Innocenti, D. Vullo, C.T. Supuran, and S.A. Poulsen Bioorg. Med. Chem. Lett. 17 2007 987 992
13. M.A. Santos, S. Marques, D. Vullo, A. Innocenti, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 17 2007 1538 1543
14. F.A. Ashour, N.S. Habib, M. Taibbi, S. Dine, and A. Dine Farmaco 45 1990 1341 1349
15. E. Akbas, and I. Berber Eur. J. Med. Chem. 40 2005 401 405
16. D. Aggarwal, D. Pal, A.K. Mitra, and I.P. Kaur Int. J. Pharm. 338 2007 21 26
17. M.F. Sugrue Prog. Ret. Eye Res. 19 2000 87 112
18. C.J. Ingram, and R.F. Brubaker Am. J. Ophthalmol. 128 1999 292 296
19. A. Konowal, J.C. Morrison, S.V.L. Brown, D.L. Cooke, L.J. Maguire, D.V. Verdier, F.T. Fraunfelder, R.F. Dennis, and R.J. Epstein Am. J. Ophthalmol. 127 1998 403 406
20. A. ener, R. Kasmoullar, M.K. ener,. Bildirici, and Y. Akamur J. Heterocyclic Chem. 39 2002 869 875
21. A. ener, R. Kasmoullar, M.K. ener, and H. Gen Chem. Heterocyclic Compd. 8 2004 1201 1208
22. B.K. Kaymakolu, and S. Rollas Farmaco 57 2002 595 599
23. H.R. Stevens, and F.W. Ward J. Chem. Soc. 125 1924 1324 1329
24. P.G. Baraldi, S. Manfredini, R. Romagnoli, L. Stevanato, A.N. Zaid, and R. Manservigi Nucleos. Nucleot. 17 1998 2165 2173
25. G.J. Hatheway, C. Hansch, K.H. Kim, S.R. Milstein, C.L. Schimidt, R.N. Smith, and F.R. Quinn J. Med. Chem. 21 1978 563 574
26. J.A. Secrist, and P.S. Liu J. Org. Chem. 43 1978 3937 3941
27. R. Kasmoullar, M. Bülbül, H. Günhan, and H. Güleryüz Bioorg. Med. Chem. 17 2009 3295 3301
28. O. Arslan, B. Nalbantolu, N. Demir, H. Özdemir, and Ö.. Küfreviolu Turk. J. Med. Sci. 26 1996 163 166
29. E.E. Rickli, S.A. Ghazanfar, B.H. Gibbson, and J.T. Edsall J. Biol. Chem. 239 1964 1065 1078
30. M.M. Bradford Anal. Biochem. 72 1976 248 251
31. U.K. Laemmli Nature 227 1970 680 685
32. K.M. Wilbur, and N.G. Anderson J. Biol. Chem. 176 1948 147 154
33. C. Landolfi, M. Marchetti, G. Ciocci, and C. Milanese J. Pharmac. Toxic. Meth. 38 1997 169 172
34. M. Bülbül, O. Hisar,. Beydemir, M. ifti, and Ö.. Küfreviolu J. Enz. Inhib. Med. Chem. 18 2003 371 375
35. M. ifti, M. Bülbül, M. Gül, K. Gümütekin,. Dane, and H. Süleyman J. Enz. Inhib. Med. Chem. 20 2005 103 108
36. O. Hisar,. Beydemir, M. Bülbül, and T.J. Yank J. Appl. Anim. Res. 30 2006 185 188
37. J.Y. Winum, A. Cecchi, J.L. Montero, A. Innocenti, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 15 2005 3302 3306