Structure-based design and synthesis of novel pseudosaccharine derivatives as antiproliferative agents and kinase inhibitors

European Journal of Medicinal Chemistry

Volumn 61, Issue , 2013, Pages 122-131

  Elsayed, Mohamed S A ^a   El Araby, Moustafa E ^b   Serya, Rabah A T ^a   El Khatib, Ahmed H ^c   Linscheid, Michael W ^c   Abouzid, Khaled A M ^a  

^a African Union Organization St Abbassia   (Egypt)

^b Helwan   (Egypt)

^c HUMBOLDT UNIVERSITY   (Germany)

Author keywords

Antiproliferative; Benzo d isothiazole 1,1 dioxide; Docking; Kinase; Pseudosaccharine

Indexed keywords

1 (4 CHLOROPHENYL) 3 [3 [(2,4 DICHLOROPHENYL)AMINO] 1,1 DIOXIDOBENZO[D]ISOTHIAZOL 5 YL]UREA; ANTINEOPLASTIC AGENT; MOLECULAR SCAFFOLD; PHOSPHOTRANSFERASE INHIBITOR; QUINAZOLINE; UNCLASSIFIED DRUG;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CELL LINE; CONTROLLED STUDY; DRUG DESIGN; DRUG MECHANISM; HUMAN; HUMAN CELL; SRC HOMOLOGY DOMAIN;

ANTINEOPLASTIC AGENTS; CELL CYCLE; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; CYCLIC S-OXIDES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MCF-7 CELLS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHENYLUREA COMPOUNDS; PROTEIN KINASE INHIBITORS; PROTEIN KINASES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84874930935     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.09.039     Document Type: Article

References (40)

1. J. Zhang, P.L. Yang, and N.S. Gray Nat. Rev. Cancer 9 2009 28 39
2. A.C. Dar, and K.M. Shokat Annu. Rev. Biochem. 80 2011 769 795
3. A. Birnbaum, and N. Ready Curr. Treat. Options Oncol. 6 2005 75 81
4. N. Starling, J. Neoptolemos, and D. Cunningham Ther. Clin. Risk Manag. 2 2006 435 445
5. L.A. Byers, and J.V. Heymach Clin. Lung Cancer 2 8 Suppl 2007 S79 S85
6. Y. Liu, and N.S. Gray Nat. Chem. Biol. 2 2006 358 364
7. S.K. Srivastava, V. Kumar, S.K. Agarwal, R. Mukherjee, and A.C. Burman Anti-cancer Agents Med. Chem. 9 2009 246 275
8. O. Fedorov, S. Muller, and S. Knapp Nat. Chem. Biol. 6 2010 166 169
9. O. Cruz-Lopez, A. Conejo-Garcia, M.C. Nunez, M. Kimatrai, M.E. Garcia-Rubino, F. Morales, V. Gomez-Perez, and J.M. Campos Curr. Med. Chem. 18 2011 943 963
10. L. Shewchuk, A. Hassell, B. Wisely, W. Rocque, W. Holmes, J. Veal, and L.F. Kuyper J. Med. Chem. 43 1999 133 138
11. LEAD IT 1.2, in: B. GmbH (Ed.), BiosolveIT GmbH, Sankt Augustin, Germany.
12. K. Amin, H. Georgey, and F. Awadallah Med. Chem. Res. 20 2011 1042 1053
13. J. Dumas, R.A. Smith, and T.B. Lowinger Curr. Opin. Drug Discov. Dev. 7 2004 600 616
14. A. Garofalo, L. Goossens, P. Six, A. Lemoine, S. Ravez, A. Farce, and P. Depreux Bioorg. Med. Chem. Lett. 21 2011 2106 2112
15. G.F. D'alelio, W.A. Fessler, and D.M. Feigl LMSA 3 1969 941 958
16. J.A. Linn, T. Longstaff, K.L. STEVENS, WO/2008/024634 (2008).
17. A. Kreuchunas J. Org. Chem. 21 1956 368 369
18. L. Xu, H. Shu, Y. Liu, S. Zhang, and M.L. Trudell Tetrahedron 62 2006 7902 7910
19. H.B. Rode, T. Sprang, A. Besch, J. Loose, and H.H. Otto Pharmazie 60 2005 723 731
20. R.B. Brundrett, and E.H. White J. Am. Chem. Soc. 96 1974 7497 7502
21. L. Kas'yan, A. Serbin, A. Kas'yan, D. Karpenko, and E. Golodaeva Russ. J. Org. Chem. 44 2008 340 347
22. S. El Kharrat, P. Laurent, and H. Blancou J. Org. Chem. 71 2006 6742 6752
23. A.F. Brigas, and R.A.W. Johnstone Tetrahedron Lett. 31 1990 5789 5790
24. R.H. Shoemaker Nat. Rev. Cancer 6 2006 813 823
25. H.-Q. Li, P.-C. Lv, T. Yan, H.-L. Zhu, Anti-cancer Agents Med. Chem. 9 471-480.
26. M. Mannion, S. Raeppel, S. Claridge, N. Zhou, O. Saavedra, L. Isakovic, L. Zhan, F. Gaudette, F. Raeppel, R. Déziel, N. Beaulieu, H. Nguyen, I. Chute, C. Beaulieu, I. Dupont, M.-F. Robert, S. Lefebvre, M. Dubay, J. Rahil, J. Wang, H. Ste-Croix, A. Robert Macleod, J.M. Besterman, and A. Vaisburg Bioorg. Med. Chem. Lett. 19 2009 6552 6556
27. A. Zhao, X. Gao, Y. Wang, J. Ai, Y. Wang, Y. Chen, M. Geng, and A. Zhang Bioorg. Med. Chem. 19 2011 3906 3918
28. S. Claridge, F. Raeppel, M.-C. Granger, N. Bernstein, O. Saavedra, L. Zhan, D. Llewellyn, A. Wahhab, R. Deziel, J. Rahil, N. Beaulieu, H. Nguyen, I. Dupont, A. Barsalou, C. Beaulieu, I. Chute, S. Gravel, M.-F. Robert, S. Lefebvre, M. Dubay, R. Pascal, J. Gillespie, Z. Jin, J. Wang, J.M. Besterman, A.R. MacLeod, and A. Vaisburg Bioorg. Med. Chem. Lett. 18 2008 2793 2798
29. L. Jin, A. Fuchs, S.J. Schnitt, Y. Yao, A. Joseph, K. Lamszus, M. Park, I.D. Goldberg, and E.M. Rosen Cancer 79 1997 749 760
30. T. Sawyer, B. Boyce, D. Dalgarno, and J. Iuliucci Expert Opin. Investig. Drugs 10 2001 1327 1344
31. M.C. Frame Biochim. Biophys. Acta 1602 2002 114 130
32. J. Das, P. Chen, D. Norris, R. Padmanabha, J. Lin, R.V. Moquin, Z. Shen, L.S. Cook, A.M. Doweyko, S. Pitt, S. Pang, D.R. Shen, Q. Fang, H.F. de Fex, K.W. McIntyre, D.J. Shuster, K.M. Gillooly, K. Behnia, G.L. Schieven, J. Wityak, and J.C. Barrish J. Med. Chem. 49 2006 6819 6832
33. B. Barlaam, M. Fennell, H. Germain, T. Green, L. Hennequin, R. Morgentin, A. Olivier, P. Plé, M. Vautier, and G. Costello Bioorg. Med. Chem. Lett. 15 2005 5446 5449
34. D.H. Boschelli, D. Wang, Y. Wang, B. Wu, E.E. Honores, A.C. Barrios Sosa, I. Chaudhary, J. Golas, J. Lucas, and F. Boschelli Bioorg. Med. Chem. Lett. 20 2010 2924 2927
35. F.M. Johnson, B. Saigal, M. Talpaz, and N.J. Donato Clin. Cancer Res. 11 2005 6924 6932
36. X.-F. Zhu, Z.-C. Liu, B.-F. Xie, Z.-M. Li, G.-K. Feng, D. Yang, and Y.-X. Zeng Cancer Lett. 169 2001 27 32
37. G. Jones, P. Willett, R.C. Glen, A.R. Leach, and R. Taylor J. Mol. Biol. 267 1997 727 748
38. C. Naegeli, A. Tyabji, and L. Conrad Helv. Chim. Acta 21 1938 1127 1143
39. K.L. Widdowson, D.F. Veber, A.J. Jurewicz, R.P. Hertzberg, M.C. Rutledge Jr., US5886044, (1999).
40. Accelry's Discovery Studio 2.5.5 2010 Accelrys Software Inc. San Diego