N-benzylisatin sulfonamide analogues as potent caspase-3 inhibitors: Synthesis, in vitro activity, and molecular modeling studies

Journal of Medicinal Chemistry

Volumn 48, Issue 24, 2005, Pages 7637-7647

  Chu, Wenhua ^a   Zhang, Jun ^a   Zeng, Chenbo ^a   Rothfuss, Justin ^a   Tu, Zhude ^a   Chu, Yunxiang ^a   Reichert, David E ^a   Welch, Michael J ^a   Mach, Robert H ^a  

^a WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 (2 PHENOXYMETHYLPYRROLIDINE 1 SULFONYL)ISATIN DERIVATIVE; AZETIDINE ISATIN DERIVATIVE; CASPASE 3; CASPASE 3 INHIBITOR; CASPASE 6; CASPASE 7; CASPASE 8; INTERLEUKIN 1BETA CONVERTING ENZYME; N BENZYLISATIN SULFONAMIDE DERIVATIVE; PYRIDINE DERIVATIVE; PYRROLIDINE ISATIN DERIVATIVE; SULFONAMIDE; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; DRUG ACTIVITY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; MOLECULAR MODEL; TISSUE INJURY;

APOPTOSIS; BENZYL COMPOUNDS; CASPASE 3; CASPASES; ISATIN; MODELS, MOLECULAR; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 28144443339     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0506625     Document Type: Article

References (25)

1. Jacobson, M. D.; Weil, M.; Raff, M. C. Programmed Cell Death in Animal Development. Cell 1997, 88, 347-354.
2. Reed, J. C. Apoptosis-based Therapies. Nature Rev. Drug Discovery 2002, 1, 111-121.
3. Rodriguez, I.; Matsuura, K.; Ody, C.; Nagata, S.; Vassalli, P. Systemic injection of a tripeptide inhibits the intracellular activation of CPP32-like proteases in vivo and fully protects mice against Fas-mediated fulminant liver destruction and death. J. Exp. Med. 1996, 184, 2067-2072.
4. O'Brien, T.; Lee, D. Prospects for caspase inhibitors. Mini Rev. Med. Chem. 2004, 4, 153-165.
5. Denault, J.-B.; Salvesen, G. S. Capsases: keys in the ignition of cell death. Chem. Rev. 2002, 702, 4489-4499.
6. Garcia-Calvo, M.; Peterson, E. P.; Leiting, B.; Ruel, R.; Nicholson, D. W.; Thornberry, N. A. Inhibition of human caspases by peptide-based and macromolecular inhibitors. J. Biol. Chem. 1998, 273, 32608-32613.
7. Hotchkiss, R. S.; Chang, K. C.; Swanson, P. E.; Tinsley, K. W.; Hui, J. J.; Klender, P.; Xanthoudakis, S.; Roy, S.; Black, C.; Grimm, E.; Aspiotis, R.; Han, Y.; Nicholson, D. W.; Karl, I. E. Caspase inhibitors improve survival in sepsis: a critical role of the lymphocyte. Nature Immunol. 2000, 1, 496-501.
8. Choong, I. C.; Lew, W.; Lee, D.; Pham, P.; Burdett, M. T.; Lam, J. W.; Wiesmann, C.; Luong, T. N.; Fahr, B.; DeLano, W. L.; McDowell, R. S.; Allen, D. A.; Erlanson, D. A.; Gordon, E. M.; O'Brien, T. Identification of potent and selective small-molecule inhibitors of caspase-3 through the use of extended tethering and structure-based drug design. J. Med. Chem. 2002,45, 5005-5022.
9. Linton, S. D.; Karanewsky, D. S.; Ternansky, R. J.; Wu, J. C.; Pham, B.; Kodandapani, L.; Smidt, R.; Diaz, J.-L.; Fritz, L. C.; Tomaselli, K. J. Acyl peptides as reversible caspase inhibitors. Part 1: Initial lead optimization. Bioorg. Med. Chem. Lett. 2002. 12, 2969-2971.
10. Linton, S. D.; Karanewsky, D. S.; Ternansky, R. J.; Chen, N.; Guo, X.; Jahangiri, K. G.; Kalish, V. J.; Meduna, S. P.; Robinson, E. D.; Ullman, B. R.; Wu, J. C.; Pham, B.; Kodandapani, L.; Smidt, R.; Diaz, J.-L.; Fritz, L. C.; von Krosigk, U.; Roggo, S.; Schmitz, A.; Tomaselli, K. J. Acyl peptides as reversible caspase inhibitors. Part 2: Further optimization. Bioorg. Med. Chem. Lett. 2002, 12, 2969-2971.
11. Han, Y.; Giroux, A.; Grimm, E. L.; Aspiotis, R.; Francoeur, S.; Bayly, C. I.; Mckay, D. J.; Roy, S.; Xanthoudakis, S.; Vallancourt, J. P.; Rasper, D. M.; Tam, J.; Tawa, P.; Thornberry, N. A.; Paterson, E. P.; Garcia-Calvo, M.; Becker, J. W.; Rotonda, J.; Nicholson, D. W.; Zamboni, R. J. Discovery of novel aspartyl ketone dipeptides as potent and selective caspase-3 inhibitors. Bioorg. Med. Chem. Lett. 2004, 14, 805-808.
12. Becker, J. W.; Rotonda, J.; Soisson, S. M.; Aspiotis, R.; Bayly, C.; Francoeur, S.; Gallant, M.; Garcia-Calvo, M.; Giroux, A.; Grimm, E.; Han, Y.; McKay, D.; Nicholson, D. W.; Peterson, E.; Renaud, J.; Roy, S.; Thornberry, N.; Zamboni, R. Reducing the peptidyl features of caspase-3 inhibitors: a structural analysis. J. Med. Chem. 2004, 47, 2466-2474.
13. Han, B. H.; Xu, D.; Choi, J.; Han, Y.; Xanthoudakis, S.; Roy, S.; Tam, J.; Vaillancourt, J.; Colucci, J.; Siman, R.; Giroux, A.; Robertson, G. S.; Zamboni, R.; Nicholson, D. W.; Holtzman, D. M. Selective, reversible caspase-3 inhibitor is neuroprotective and reveals distinct pathways of cell death after neonatal hypoxia-ischemia brain injury. J. Biol. Chem. 2002,277, 30128-31036.
14. Lee, D.; Long, S. A.; Adams, J. L.; Chan, G.; Vaidya, K. S.; Francis, T. A.; Kikly, K; Winkler, J. D.; Sung, C.-M.; Debouck, C.; Richardson, S.; Levy, M. A.; DeWolf, W. E., Jr.; Keller, P. M.; Tomaszek, T.; Head, M. S.; Ryan, M. D.; Haltiwanger, R. C.; Liang, P.-H.; Janson, C. A.; McDevitt, P. J.; Johanson, K.; Concha, N. O.; Chan, W.; Abdel-Meguid, S. S.; Badger, A. M.; Lark, M. W.; Nadeau, D. P.; Suva, L. J.; Gowen, M.; Nuttall, M. E. Potent and selective nonpeptide inhibitors of caspases 3 and 7 inhibit apoptosis and maintain cell functionality. J. Biol. Chem. 2000, 275, 16007-16104.
15. Chapman, J. G.; Magee, W. P.; Stukenbrok, H. A.; Beckius, G. E.; Milici, A. J.; Tracey, W. R. A novel nonpeptidic caspase 3/7 inhibitor, (S)-(+)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]-isatin reduces myocardial ischemic injury. Eur. J. Pharmacol. 2002, 456, 59-68.
16. Lee, D.; Long, S. A.; Murray, J. H.; Adams, J. L.; Nutall, M. E.; Nadeau, D. P.; Kikly, K.; Winkler, J. D.; Sung, C.-M.; Ryan, D.; Levy, M. A.; Keller, P. M.; DeWolf, W. E., Jr. Potent and selective nonpeptide inhibitors of caspases 3 and 7. J. Med. Chem. 2001, 44, 2015-2026.
17. Abreo, M. A.; Lin, N.; Garvey, D. S.; Gunn, D. E.; Hettinger, A.; Wasicak, J. T.; Paulik, P. A.; Martin, Y. C.; Dannelly-Roberts, D. L.; Anderson, D. J.; Sullivan, J. P.; Williams, M.; Arneric, S. P.; Holladay, M. W. Novel 3-pyridyl ethers with subnanomolar affinity for central nicotinic acetylcholine receptors. J, Med. Chem. 1996, 39, 817-825.
18. Wildman, S. A.; Crippen, G. M. Prediction of Physicochemical Parameters by Atomic Contributions. J. Chem. Inf. Comput. Sci. 1999, 39, 868-873.
19. Stanton, D. T.; Jurs, P. C. Development and Use of Charged Partial Surface Area Structural Descriptors in Computer-Assisted Quantitative Structure-Property Relationship Studies. Anal. Chem. 1990, 62, 2323-2329.
20. Wallace, A. C.; Laskowski, R. A.; Thornton, J. M. LIGPLOT: A Program to generate schematic diagrams of protein - ligand interactions. Protein Eng. 1995, 8, 127-124.
21. Sullivan, P. T.; Sullivan, C. B.; Norton, S. J. α-Fluoro- and α-hydroxypyridylalanines. J. Med. Chem. 1971, 14, 211-214.
22. Berman, H. M.; Westbrook, J.; Feng, Z.; Gilliland, G.; Bhat, T. N. et al. The Protein Data Bank. Nucleic Acids Res. 2000, 28, 235-242.
23. Molecular Operating Environment (MOE); 2004.03 ed.; Chemical Computing Group: Montreal, Canada.
24. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M. et al. Macromodel - an Integrated Software System for Modeling Organic and Bioorganic Molecules Using Molecular Mechanics. J. Comput. Chem. 1990, 11, 440.
25. Jones, G.; Willett, P.; Glen, R. C.; Leach, A. R.; Taylor, R. Development and Validation of a Genetic Algorithm for Flexible Docking. J. Mol. Biol. 1997, 267, 727-748.