Improved synthesis and structural reassignment of MC1568: A class IIa selective HDAC inhibitor

Journal of Medicinal Chemistry

Volumn 57, Issue 3, 2014, Pages 1132-1135

  Fleming, Cassandra L ^a   Ashton, Trent D ^a   Gaur, Vidhi ^b   McGee, Sean L ^b   Pfeffer, Frederick M ^a  

^a DEAKIN UNIVERSITY   (Australia)

^b DEAKIN UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

HISTONE DEACETYLASE INHIBITORS; HYDROXAMIC ACIDS; MOLECULAR STRUCTURE; PYRROLES;

EID: 84894034702     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm401945k     Document Type: Article

References (24)

1. Paris, M.; Porcelloni, M.; Binaschi, M.; Fattori, D. Histone Deacetylase Inhibitors: From Bench to Clinic J. Med. Chem. 2008, 51, 1505-1529
2. Miller, T. A.; Witter, D. J.; Belvedere, S. Histone Deacetylase Inhibitors J. Med. Chem. 2003, 46, 5097-5116
3. McKinsey, T. A. Isoform-Selective HDAC Inhibitors: Closing In on Translational Medicine for the Heart J. Mol. Cell. Cardiol. 2011, 51, 491-496
4. Suzuki, T. Explorative Study on Isoform-Selective Histone Deacetylase Inhibitors Chem. Pharm. Bull. 2009, 57, 897-906
5. Bertrand, P. Inside HDAC with HDAC Inhibitors Eur. J. Med. Chem. 2010, 45, 2095-2116
6. Balasurbramanain, S.; Verner, E.; Buggy, J. J. Isoform-Specific Histone Deacetylase Inhibitors: The Next Step? Cancer Lett. 2009, 280, 211-221
7. Bieliauskas, A. V.; Pflum, M. K. H. Isoform-Selective Histone Deacetylase Inhibitors Chem. Soc. Rev. 2008, 37, 1402-1413
8. Haberland, M.; Montgomery, R. L.; Olson, E. N. The Many Roles of Histone Deacetylases in Development and Physiology: Implications for Disease and Therapy Nat. Rev. Genet. 2009, 10, 32-42
9. Christensen, D. P.; Dahllöf, M.; Lundh, M.; Rasmussen, D. N.; Nielsen, M. D.; Billestrup, N.; Grunnet, L. G.; Mandrup-Poulsen, T. Histone Deacetylase (HDAC) Inhibition as a Novel Treatment for Diabetes Mellitus Mol. Med. 2011, 17, 378-390
10. Celgene Invests $15M in Acetylation To Support HDAC Inhibitor Development. Genet. Eng. Biotechnol. News. 2012, February 9.
11. Lobera, M.; Madauss, K. P.; Pohlhaus, D. T.; Wright, Q. G.; Tracha, M.; Schmidt, D. R.; Baloglu, E.; Trump, R. P.; Head, M. S.; Hofmann, G. A.; Murray-Thompson, M.; Schwartz, B.; Chakravorty, S.; Wu, Z.; Mander, P. K.; Kruidenier, L.; Reid, R. A.; Burkhart, W.; Turunen, B. J.; Rong, J. X.; Wagner, C.; Moyer, M. B.; Wells, C.; Hong, X.; Moore, J. T.; Williams, J. D.; Soler, D.; Ghosh, S.; Nolan, M. A. Selective Class IIa Histone Deacetylase Inhibition via Nonchelating Zinc-Binding Group Nat. Chem. Biol. 2013, 9, 319-325
12. Kong, Y.; Jung, M.; Wang, K.; Grindrod, S.; Velena, A.; Lee, S. A.; Dakshanamurthy, A.; Yang, Y.; Miessau, M.; Zheng, C.; Dritschilo, A.; Brown, M. L. Histone Deacetylase Cytoplasmic Trapping by a Novel Fluorescent HDAC Inhibitor Mol. Cancer Ther. 2011, 10, 1591-1599
13. Tessier, P.; Smil, D. V.; Wanhhab, A.; Leit, S.; Rahil, J.; Li, Z.; Déziel, R.; Besterman, J. M. Diphenylmethylene Hydroxamic Acids as Selective Class IIa Histone Deacetylase Inhibitors Bioorg. Med. Chem. Lett. 2009, 19, 5684-5688
14. Mai, A.; Massa, S.; Pezzi, R.; Simeoni, S.; Rotili, D.; Nebbioso, A.; Scognamiglio, A.; Altucci, L.; Loidl, P.; Brosch, G. Class II (IIa)-Selective Histone Deacetylase Inhibitors. 1. Synthesis and Biological Evaluation of Novel (Aryloxopropenyl)pyrrolyl Hydroxyamides J. Med. Chem. 2005, 48, 3344-3353
15. Rango, R.; Simeoni, S.; Rotili, D.; Caroli, A.; Botta, G.; Brosch, G.; Massa, S.; Mai, A. Class II-Selective Histone Deacetylase Inhibitors. Part 2: Alignment-Independent GRIND 3-D QSAR, Homology and Docking Studies Eur. J. Med. Chem. 2008, 43, 621-631
16. Kahali, B.; Gramling, S. J. B.; Marquez, S. B.; Thompson, K.; Lu, L.; Reisman, D. Identifying Targets for the Restoration and Reactivation of BRM Oncogene 2013, 1-12
17. Palmisano, I.; Chiara, G. D.; D'Ambrosio, R. L.; Huichalaf, C.; Brambilla, P.; Corbetta, S.; Riba, M.; Piccirillo, R.; Valente, S.; Casari, G.; Mai, A.; Boneschi, F. M.; Gabellini, D.; Poli, G.; Schiaffino, M. V. Amino Acid Starvation Induces Reactivation of Silenced Transgenes and Latent HIV-1 Provirus via Down-Regulation of Histone Deacetylase 4 (HDAC4) Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 2284-2293
18. Munkacsi, A. B.; Chen, F. W.; Brinkman, M. A.; Higaki, K.; Gutiérrez, G. D.; Chaudharis, J.; Layer, J. V.; Tong, A.; Bard, M.; Boone, C.; Ioannou, Y. A.; Sturley, S. L. An "Exacerbate-Reverse" Strategy in Yeast Identifies Histone Deacetylase Inhibition as a Correction for Cholesterol and Sphingolipid Transport Defects in Human Niemann-Pick Type C Disease J. Biol. Chem. 2011, 286, 23842-23851
19. Gupton, J. T.; Banner, E. J.; Sartin, M. D.; Coppock, M. B.; Hempel, J. E.; Kharlamova, A.; Fisher, D. C.; Giglio, B. C.; Smith, K. L.; Keough, M. J.; Smith, T. M.; Kanters, R. P. F.; Dominey, R. N.; Sikorski, J. A. The Application of Vinylogous Iminium Salt Derivatives and Microwave Accelerated Vilsmeier-Haack Reactions to Efficient Relay Synthesis of the Polycitone and Storniamide Natural Products Tetrahedron 2008, 64, 5246-5253
20. Katrikzky, A. R; Akhmedov, N. G.; Doskocz, J.; Mohapatra, P. P.; Hall, C. D.; Güven, A. NMR Spectra, GIAO and Charge Density Calculations of Five-Membered Aromatic Heterocycles Magn. Reson. Chem. 2007, 45, 532-543
21. Barker, P.; Gendler, P.; Rapoport, H. 2-(Trichloroacetyl)pyrroles as Intermediates in the Preparation of 2,4-Disubstituted Pyrroles J. Org. Chem. 1978, 25, 4849-4853
22. 4 Substitutions on Biological Activity J. Med. Chem. 2004, 47, 1098-1109
23. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4 th ed.; Blackwell Science Ltd.: Oxford, U.K., 2000; Chapter 13, pp 241-243.
24. Mai, A.; Massa, S.; Pezzi, R.; Rotili, D.; Loidl, P.; Brosch, G. Discovery of (Aryloxopropenyl)pyrrolyl Hydroxyamides as Selective Inhibitors of Class IIa Histone Deacetylase Homologue HD1-A J. Med. Chem. 2003, 46, 4826-4829