Design, synthesis and evaluation of 1,2-benzisothiazol-3-one derivatives as potent caspase-3 inhibitors

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 11, 2013, Pages 2960-2967

  Liu, Dazhi ^b   Tian, Zhen ^b   Yan, Zhihui ^a   Wu, Lixin ^a   Ma, Yan ^b   Wang, Quan ^b   Liu, Wei ^a   Zhou, Honggang ^b,c   Yang, Cheng ^b,c  

^a TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b NANKAI UNIVERSITY   (China)

^c TEDA   (China)

Author keywords

1,2 Benzisothiazol 3 one; Apoptosis; Caspase 3; Inhibitor

Indexed keywords

1,2 BENZISOTHIAZOL 3 ONE DERIVATIVE; 2 (4 FLUOROBENZYL) 2 HYDROBENZO[D]ISOTHIAZOL 3 ONE; 2 [3 (TRIFLUOROMETHYL)PHENYL] 2 HYDROBENZO[D]ISOTHIAZOL 3 ONE; 2 METHYL 2 HYDROBENZO[D]ISOTHIAZOL 3 ONE; 2 PHENETHYL 2 HYDROBENZO[D]ISOTHIAZOL 3 ONE; 2 PHENYL 2 HYDROBENZO[D]ISOTHIAZOL 3 ONE; CASPASE 3; CASPASE 3 INHIBITOR; ISOTHIAZOLE DERIVATIVE; N (2 BROMOPHENYL) 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; N (2 FLUOROBENZYL) 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; N (2 METHOXYBENZYL) 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; N (2 METHOXYPHENYL) 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; N (2 NITROPHENYL) 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; N (3 BROMOPHENYL) 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; N (3 FLUOROBENZYL) 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; N (3 FLUOROPHENYL) 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; N (3 METHOXYPHENYL) 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; N (4 BROMOPHENYL) 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; N (4 FLUOROBENZYL) 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; N (4 FLUOROPHENYL) 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; N (4 IODOPHENYL) 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; N (4 METHOXYPHENYL) 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; N [4 CHLORO 3 (TRIFLUOROMETHYL)PHENYL] 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; N BENZYL 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; N ETHYL 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; N PHENETHYL 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; N PHENYL 3 OXOBENZO[D]ISOTHIAZOLE 2(3H) CARBOXAMIDE; RECOMBINANT CASPASE 3; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; HIGH THROUGHPUT SCREENING; IC 50; IN VITRO STUDY; MOLECULAR MODEL; STRUCTURE ACTIVITY RELATION;

CASPASE 3; CASPASE INHIBITORS; DRUG DESIGN; ENZYME ASSAYS; HIGH-THROUGHPUT SCREENING ASSAYS; HUMANS; MOLECULAR DOCKING SIMULATION; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 84877795432     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.03.075     Document Type: Article

References (26)

1. B. Howley, and H.O. Fearnhead J. Cell. Mol. Med. 12 2008 1502
2. J.B. Denault, and G.S. Salvesen Chem. Rev. 102 2002 4489
3. N.A. Thornberry, and Y. Lazebnik Science 281 1998 1312
4. W.H. Chu, J. Rothfuss, A. d'Avignon, C. Zeng, D. Zhou, R.S. Hotchkiss, and R.H. Mach J. Med. Chem. 50 2007 3751
5. A.K. Podichetty, S. Wagner, S. Schröer, A. Faust, M. Schäfers, O. Schober, K. Kopka, and G. Haufe J. Med. Chem. 52 2009 3484
6. A.G. Porter, and R.U. Jänicke Cell Death Differ. 6 1999 99
7. A. Fleischer, A. Ghadiri, F. Dessauge, M. Duhamel, M.P. Rebollo, F. Alvarez-Franco, and A. Rebollo Mol. Immunol. 43 2006 1065
8. R.C. Taylor, S.P. Cullen, and S.J. Martin Nat. Rev. Mol. Cell Biol. 9 2008 231
9. M. Garcia-Calvo, E.P. Peterson, B. Leiting, R. Ruel, D.W. Nicholson, and N.A. Thornberry J. Biol. Chem. 273 1998 32608
10. W. Yang, J. Guastella, J.C. Huang, Y. Wang, L. Zhang, D. Xue, M. Tran, R. Woodward, S. Kasibhatla, B. Tseng, J. Drewe, and S.X. Cai Br. J. Pharmacol. 140 2003 402
11. Y. Han, A. Giroux, E.L. Grimm, R. Aspiotis, S. Francoeur, C.I. Bayly, D.J. Mckay, S. Roy, S. Xanthoudakis, J.P. Vaillancourt, D.M. Rasper, J. Tam, P. Tawa, N.A. Thornberry, E.P. Paterson, M. Garcia-Calvo, J.W. Becker, J. Rotonda, D.W. Nicholson, and R.J. Zamboni Bioorg. Med. Chem. Lett. 14 2004 805
12. J.W. Becker, J. Rotonda, S.M. Soisson, R. Aspiotis, C. Bayly, S. Francoeur, M. Gallant, M. Garcia-Calvo, A. Giroux, E. Grimm, Y. Han, D. McKay, D.W. Nicholson, E. Peterson, J. Renaud, S. Roy, N. Thornberry, and R. Zamboni J. Med. Chem. 47 2004 2466
13. N. Micale, R. Vairagoundar, A.G. Yakovlev, and A.P. Kozi-kowski J. Med. Chem. 47 2004 6455
14. J. Yang, and V.H. Trond Bioorg. Med. Chem. Lett. 21 2011 1626
15. D.V. Kravchenko, V.M. Kysil, S.E. Tkachenko, S. Maliarchouk, I.M. Okun, and A.V. Ivachtchenko Eur. J. Med. Chem. 40 2005 1377
16. D.V. Kravchenko, V.V. Kysil, A.P. Ilyn, S.E. Tkachenko, S. Maliarchouk, I.M. Okun, and A.V. Ivachtchenko Bioorg. Med. Chem. Lett. 2005 1841 15
17. Y.H. Chen, Y.H. Zhang, H.J. Zhang, D.Z. Liu, M. Gu, J.Y. Li, F. Wu, X.Z. Zhu, J. Li, and F. Nan J. Med. Chem. 49 2006 1613
18. J.Q. Du, J. Wu, H.J. Zhang, Y.H. Zhang, B.Y. Qiu, F. Wu, Y.H. Chen, J.Y. Li, F.J. Nan, J.P. Ding, and J. Li J. Biol. Chem. 283 2008 30205
19. G. Von Tacconi, P.P. Righetti, and G. Desimoni J. Prakt. Chem. (Leipzig) 315 1973 339
20. P. Majer, and R.S. Randad J. Org. Chem. 1994 1937 59
21. Coordinates for the caspase-3 complex with co-crystallized inhibitor, have been deposited in the Protein Data Bank under PDB ID code 3H0E, together with the corresponding structure.
22. C.-Z. Ni, C.L. Li, J.C. Wu, A.P. Spada, and K.R. Ely J. Mol. Recognit. 16 2003 121
23. B. Fang, P.I. Boross, J. Tozser, and I.T. Weber Mol. Biol. 360 2006 654
24. P.J. Lakshmi, B.V.S. Suneel Kumar, R.S. Nayana, M.S. Mohan, R. Bolligarla, S.K. Das, M.U. Bhanu, A.K. Kondapi, and M. Ravikumar Bioorg. Med. Chem. 17 2009 6040
25. I. Okun, S. Malarchuk, E. Dubrovskaya, A. Khvat, S. Tkachenko, V. Kysil, D. Kravchenko, and A. Ivachtchenko J. Biomol. Screen. 11 2006 694
26. SYBYL-X 1.1 2010 Tripos Inc. St. Louis, MO