Novel aminophenyl benzamide-type histone deacetylase inhibitors with enhanced potency and selectivity

Journal of Medicinal Chemistry

Volumn 50, Issue 23, 2007, Pages 5543-5546

  Moradei, Oscar M ^a   Mallais, Tammy C ^a   Frechette, Sylvie ^a   Paquin, Isabelle ^a   Tessier, Pierre E ^a   Leit, Silvana M ^a   Fournel, Marielle ^a   Bonfils, Claire ^a   Trachy Bourget, Marie Claude ^a   Liu, Jianhong ^a   Yan, Theresa P ^a   Lu, Ai Hua ^a   Rahil, Jubrail ^a   Wang, James ^a   Lefebvre, Sylvain ^a   Li, Zuomei ^a   Vaisburg, Arkadii F ^a   Besterman, Jeffrey M ^a  

^a METHYLGENE INC   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

4 N ACETYLDINALINE; BENZAMIDE DERIVATIVE; HISTONE DEACETYLASE INHIBITOR; HYDROXAMIC ACID DERIVATIVE; MGCD 0103; N (2 AMINOPHENYL) 4 (3 PYRIDINYLMETHOXYCARBONYLAMINOMETHYL)BENZAMIDE; RECOMBINANT ENZYME; UNCLASSIFIED DRUG; VORINOSTAT;

ACUTE GRANULOCYTIC LEUKEMIA; ARTICLE; B CELL LYMPHOMA; BREAST CANCER; CANCER CELL CULTURE; CANCER CHEMOTHERAPY; CELL STRAIN HCT116; COLON CANCER; CYTOTOXICITY; DOSE RESPONSE; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; FOLLICULAR LYMPHOMA; HODGKIN DISEASE; HUMAN; HUMAN CELL; LARGE CELL LYMPHOMA; MYELODYSPLASTIC SYNDROME; T CELL LYMPHOMA;

ANTINEOPLASTIC AGENTS; BENZAMIDES; CATALYTIC DOMAIN; CELL LINE; HISTONE DEACETYLASES; HUMANS; MODELS, MOLECULAR; NADH, NADPH OXIDOREDUCTASES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 36148950575     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm701079h     Document Type: Article

References (24)

1. Jenuwein, T.; Allis, C. D. Translating the histone code. Science 2001, 293, 1074-1080.
2. Timmermann, S.; Lehrmann, H.; Polesskaya, A.; Harel-Bellan, A. Histone acetylation and disease. Cell. Mol. Life Sci. 2001, 58, 728-736.
3. Taunton, J.; Hassig, C. A.; Schreiber, S. L. A mammalian histone deacetylase related to the yeast transcriptional regulator Rpd3p. Science 1996, 272, 408-411.
4. Bolden, J. E.; Peart, M. J.; Johnstone, R. W. Anticancer activities of histone deacetylase inhibitors. Nat. Rev. Drug Discovery 2006, 5, 769-784.
5. Gregoretti, I. V.; Lee, Y.-M.; Goodson, H. V. Molecular evolution of the histone deacetylase family: functional implications of phylogenetic analysis. J. Mol. Biol. 2004, 338, 17-31.
6. (a) Bertos, N.; Wang, A.; Yang, X. Class II histone deacetylases: structure, function, and regulation. Biochem. Cell Biolog. 2001, 79, 243-252.
7. (b) Fischle, W.; Kiermer, V.; Dequiedt, F.; Verdin, E. The emerging role of Class II histone deacetylases. Biochem. Cell Biol. 2001, 79, 337-348.
8. Grozinger, C.; Schreiber. S. Deacetylase enzymes: biological functions and the use of small-molecule inhibitors. Chem. Biol. 2002, 9, 3-16.
9. Finnin, M.; Donigian, J.; Cohen, A.; Richon, V.; Rifkind, R.; Marks, P.; Breslow, R.; Pavietich, N. Strucures of a histone deacetylase homologue bound to the TSA and SAHA inhibitors. Nature 1999, 401, 188-193.
10. Nielsen, T.; Hildmann, C.; Dickmanns, A.; Schwienhorst, A.; Ficner, R. Crystal structure of a bacterial class 2 histone deacetylase homologue. J. Mol. Biol. 2005, 354, 107-120.
11. (a) Schuetz, A.; Min, J.; Loppnau, P.; Weigelt, J.; Sundstrom, M.; Arrowsmith, C.; Edwards, A.; Bochkarev, A., Plotnikov, A. PDB ID 2PQO and 2PQP.
12. (b) Vannini, A.; Volpari, C.; Filocampo, G.; Casavola, E.; Brunetti, M.; Renzoni, D.; Chakravarty, P.; Paolini, C.; De Francesco, R.; Gallinari, P.; Steinkuhlre, C.; Di Marco, S. Crystal structure of a eukaryotic zinc-dependent histone deacetylase, human HDAC8, complexed with a hydroxamic acid inhibitor. Proc Natl. Acad. Sci. U.S.A. 2004, 101, 15064-15069.
13. (c) Somoza, J.; Skene, R.; Katz, B.; Mol, C.; Ho, J.; Jennings, A.; Luong, C.; Arvai, A.; Buggy, J.; Chi, E.; Tang, J.; Sang, B.; Verner, E.; Wynands, R.; Leahy, E.; Dougan, D.; Snell, G.; Navre, M.; Knuth, M.; Swanson, R.; McRee, D.; Tari, L. Structural snapshots of human HDAC8 provide insights into the class I histone deacetylases. Structure 2004, 12, 1325-1334.
14. Wang, D. F.; Wiest, O.; Helquist, P.; Lan-Hargest, H. Y.; Wiech, N. L. On the function of the 14A long internal cavity of histone deacetylase-like protein: implications for the design of histone deacetylase inhibitors. J. Med. Chem. 2004, 47, 3409-3417.
15. Moradei, O.; Maroun, C.; Paquin, I.; Vaisburg, A. Histone deacetylase inhibitors: latest developments, trends and prospects. Curr. Med. Chem. Anticancer Agents 2005, 5, 529-560.
16. Marks, P. A.; Dokmanovic, M. Histone deacetylase inhibitors: discovery and development as anticancer agents. Expert Opin. Invest. Drugs 2005, 14, 1497-14511.
17. Haggarty, S.; Koeller, K.; Wong, J.; Butcher, R.; Schreiber, S. Multidimentional chemical genetic analysis of diversity-oriented synthesis-derived deacetylase inhibitors using cell-based assays. Chem. Biol. 2003, 10, 383-396.
18. Moradei, O.; Leit, S.; Zhou, N.; Frechette, S.; Paquin, I.; Raeppel, S.; Gaudette, F.; Bouchain, G.; Woo, S.; Vaisburg, A.; Fournel, M.; Kalita, A.; Lu, A.; Trachy-Bourget, M.; Pu, T.; Liu, Y.; Li, Z.; Rahil, J.; MacLeod, A.; Besterman, J.; Delorme, D. Substituted N-(2-Aminophenyl)-benzamides, (E)-N-(2-Aminophenyl)-acrylamides and their Analogues: Novel Classes of Histone Deacetylase Inhibitors. Bioorg. Med. Chem. Lett. 2006, 16, 4048-4052.
19. Bodner, B.; Jackman, L.; Morgan, R. NMR study of 1:1 complexes between divalent sulfur and aromatic compounds: a model for interactions in globular proteins. Biochem. Biophys. Res. Commun. 1980, 94, 807-813.
20. (a) MethylGene Inc. Inhibitors of histone deacetylase. WO 030704, 2005.
21. (b) MethylGene Inc. Inhibitors of histone deacetylase. WO 030705, 2005.
22. Seko, S.; Miyake, K.; Kawamura, N. A convenient copper-catalyzed direct amination of nitroarenes with O-alklyhydroxylamines. J. Chem. Soc., Perkin Trans. 1 1999, 1437-1444.
23. Suzuki, T.; Ando, T.; Tsuchiya, K.; Fukazawa, N.; Saito, A.; Mariko, Y.; Yamashita, T.; Nakanishi, O. Synthesis and histone deaceylase inhibitory activity of new benzamide derivatives. J. Med. Chem. 1999, 42, 3001-3003.
24. Chapleur, Y.; Castro, B. Synthetic C-glycosyl nucleosides. A new approach. J. Chem. Soc., Perkin Trans. 1 1980, 2683-2685.