Synthesis and antimalarial activity of thioetherhydroxyethylsulfonamides, potential aspartyl protease inhibitors, Part 3

European Journal of Medicinal Chemistry

Volumn 46, Issue 11, 2011, Pages 5688-5693

  Vellasco Junior, Walcimar T ^a,b   Guedes, Guilherme P ^a,d   Vasconcelos, Thatyana R A ^a   Vaz, Maria G F ^a   De Souza, Marcus V N ^b   Krettli, Antoniana U ^b   Krettli, Luisa G ^b   Aguiar, Anna Caroline C ^b   Gomes, Claudia R B ^b   Cunico, Wilson ^b,c  

^a FLUMINENSE FEDERAL UNIVERSITY   (Brazil)

^b INSTITUTO OSWALDO CRUZ   (Brazil)

^c FEDERAL UNIVERSITY OF PELOTAS   (Brazil)

^d FEDERAL RURAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

Antimalarial; Hydroxyethylsulfonamides; Thioetherhydroxyethylsulfonamides

Indexed keywords

ANTIMALARIAL AGENT; N 3 HYDROXY 1 PHENYL 4 (PYRIDIN 2 YLTHIO)BUTAN 2 YL 4 NITROBENZENESULFONAMIDE; N [3 HYDROXY 1 PHENYL 4 (PYRIDIN 2 YLTHIO)BUTAN 2 YL] 4 BROMOBENZENESULFONAMIDE; N [3 HYDROXY 1 PHENYL 4 (PYRIDIN 2 YLTHIO)BUTAN 2 YL] 4 FLUOROBENZENESULFONAMIDE; N [3 HYDROXY 1 PHENYL 4 (PYRIDIN 2 YLTHIO)BUTAN 2 YL] 4 METHOXYBENZENESULFONAMIDE; N [3 HYDROXY 1 PHENYL 4 (PYRIDIN 2 YLTHIO)BUTAN 2 YL] 4 METHYLBENZENESULFONAMIDE; N [3 HYDROXY 1 PHENYL 4 (PYRIMIDIN 2 YLTHIO)BUTAN 2 YL] 4 BROMOBENZENESULFONAMIDE; N [3 HYDROXY 1 PHENYL 4 (PYRIMIDIN 2 YLTHIO)BUTAN 2 YL] 4 FLUOROBENZENESULFONAMIDE; N [3 HYDROXY 1 PHENYL 4 (PYRIMIDIN 2 YLTHIO)BUTAN 2 YL] 4 METHOXYBENZENESULFONAMIDE; N [3 HYDROXY 1 PHENYL 4 (PYRIMIDIN 2 YLTHIO)BUTAN 2 YL] 4 METHYLBENZENESULFONAMIDE; N [3 HYDROXY 1 PHENYL 4 (PYRIMIDIN 2 YLTHIO)BUTAN 2 YL] 4 NITROBENZENESULFONAMIDE; SULFONAMIDE; THIOETHERHYDROXYETHYLSULFONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIMALARIAL ACTIVITY; ARTICLE; CELL STRAIN HEPG2; CONTROLLED STUDY; CROSS COUPLING REACTION; DRUG CYTOTOXICITY; DRUG DETERMINATION; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLASMODIUM FALCIPARUM; X RAY CRYSTALLOGRAPHY;

ANTIMALARIALS; ASPARTIC ACID PROTEASES; CHEMISTRY TECHNIQUES, SYNTHETIC; HEP G2 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PLASMODIUM FALCIPARUM; PROTEASE INHIBITORS; SULFONAMIDES;

EID: 80054895015     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.09.025     Document Type: Article

References (32)

1. A.U. Krettli Expert Opin. Drug Discov. 4 2009 95 108
2. G.H. Coombs, D.E. Goldberg, M. Klemba, C. Berry, J. Kay, and J.C. Mottram Trends Parasitol. 17 2001 532 537
3. K. Ersmark, B. Samuelsson, and A. Hallberg Med. Res. Rev. 26 2006 626 666
4. C. Boss, S. Richard-Bildstein, T. Weller, W. Fischli, S. Meyer, and C. Binkert Curr. Med. Chem. 10 2003 883 907
5. S. Parikh, J. Gut, E. Istvan, D.E. Goldberg, D.V. Havlir, and P.J. Rosenthal Antimicrob. Agents Chemother. 49 2005 2983 2985
6. K.T. Andrews, D.P. Fairlie, P.K. Madala, J. Ray, D.M. Wyatt, P.M. Hilton, L.A. Melville, L. Beattie, D.L. Gardioner, R.C. Reid, M.J. Stoermer, T. Skinner-Adams, C. Berry, and J.S. McCarthy Antimicrob. Agents Chemother. 50 2006 639 648
7. A. Brik, and C.-H. Wong Org. Biomol. Chem. 1 2003 5 14
8. A.K. Ghosh, G. Bilcer, and G. Schiltz Synthesis 2001 2203 2229
9. N. Trudel, R. Garg, N. Messier, S. Sundar, M. Ouellette, and M.J. Tremblay J. Infect. Dis 198 2008 1292 1299
10. L.R. Marcin, M.A. Higgins, F.C. Zusi, Y. Zhang, M.F. Dee, M.F. Parker, J.K. Muckelbauer, D.M. Camac, P.E. Morin, V. Ramamurthy, A.J. Tebben, K.A. Lentz, J.E. Grace, J.A. Marcinkeviciene, L.M. Kopcho, C.R. Burton, D.M. Barten, J.H. Toyn, J.E. Meredith, C.F. Albright, J.J. Bronson, J.E. Macor, and L.A. Thompson Bioorg. Med. Chem. Lett. 21 2011 537 541
11. M. Altenkämper, B. Bechem, J. Perruchon, S. Heinrich, A. Mädel, R. Ortmann, H.-M. Dahse, E. Freunscht, Y. Wang, J. Rath, A. Stich, M. Hitzler, P. Chiba, M. Lanzer, and M. Schlitzer Bioorg. Med. Chem. 17 2009 7690 7697
12. A. Scozzafava, T. Owa, A. Mastrolorenzo, and C.T. Supuran Curr. Med. Chem. 10 2003 925 953
13. I. Argyropoulou, A. Geronikaki, P. Vivini, and F. Zani Arkivoc 2009 89 102
14. L. Bouissane, S. El Kazzouli, S. Léonce, B. Pfeiffer, E.M. Rakib, and M. Khouili Bioorg. Med. Chem. 14 2006 1078 1088
15. Y.A. Al-Soud, H.H. Al-Sa'doni, B. Saeed, I.H. Jaber, M.O. Beni-Khalid, N.A. Al- Masoudi, T. Abdul-Kadir, P. La Colla, B. Busonera, T. Sanna, and R. Loddo Arkivoc 2008 225 238
16. S.M. Sondhi, A.D. Dwivedi, J. Singh, and P.P. Gupta Indian J. Chem. B. Org. 49 2010 1076 1082
17. D. Vullo, B. Steffansen, B. Brodin, C.T. Supuran, A. Scozzafava, and C.U. Nielsen Bioorg. Med. Chem. 14 2006 2418 2427
18. G. Melagraki, A. Afantitis, H. Sarimveis, O. Igglessi-Markopoulou, and C.T. Supuran Bioorg. Med. Chem. 14 2006 1108 1114
19. W. Cunico, C.R.B. Gomes, M. Moreth, D.P. Manhanini, I.H. Figueiredo, C. Penido, M.G.M.O. Henriques, F.P. Varotti, and A.U. Krettli Eur. J. Med. Chem. 44 2009 1363 1368
20. W. Cunico, C.R.B. Gomes, V. Facchinetti, M. Moreth, C. Penido, M.G.M.O. Henriques, F.P. Varotti, L.G. Krettli, A.U. Krettli, F.S. da Silva, E.R. Caffarena, and C.S. de Magalhães Eur. J. Med. Chem. 44 2009 3816 3820
21. W. Cunico, M.L.G. Ferreira, T.G. Ferreira, C. Penido, M.G.M.O. Henriques, L.G. Krettli, F.P. Varotti, and A.U. Krettli Lett. Drug Des. Discov. 5 2008 178 181
22. W. Cunico, C.R.B. Gomes, M.L.G. Ferreira, T.G. Ferreira, D. Cardinot, M.V.N. de Souza, and M.C.S. Loureno Eur. J. Med. Chem. 46 2011 974 978
23. W. Cunico, C.R.B. Gomes, E.R.T. Tiekink, W.T. Vellasco Junior, J.L. Wardell, and S.M.S.V. Wardell Acta Cryst. E66 2010 o267 o268
24. D. Bouchouk, E. Colacino, L. Toupet, N. Aouf, J. Martinez, and G. Dewynter Tetrahedron Lett. 50 2009 1100 1104
25. Z.-Q. Hu, and C.-F. Chen Tetrahedron 62 2006 3446 3454
26. J.M. Langenhan, J.D. Fisk, and S.H. Gellman Org. Lett. 3 2001 2559 2562
27. R.E. Desjardins, C.J. Canfield, J.D. Haynes, and J.D. Chulay Antimicrob. Agents Chemother. 16 1979 710 718
28. M. Zalis, L. Pang, M.S. Silveira, W.K. Milhous, and D.F. Wirth Am. J. Trop. Med. Hyg. 58 1998 630 637
29. -3.
30. G.M. Sheldrik SHELX-97 1997 University of Göttingen Germany
31. F. Denizot, and R. Lang J. Immunol. Methods 89 1986 271 277
32. M.C. de Madureira, A.P. Martins, M. Gomes, J. Paiva, A.P. da Cunha, and V. do Rosário J. Ethnopharmacol. 81 2002 23 29