Conformationally locked calixarene-based histone deacetylase inhibitors

Organic Letters

Volumn 12, Issue 23, 2010, Pages 5382-5385

  Chini, Maria Giovanna ^a   Terracciano, Stefania ^a   Riccio, Raffaele ^a   Bifulco, Giuseppe ^a   Ciao, Roberta ^a   Gaeta, Carmine ^a   Troisi, Francesco ^a   Neri, Placido ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; HISTONE DEACETYLASE INHIBITOR;

ARTICLE; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; PROTEIN DOMAIN;

CALIXARENES; HISTONE DEACETYLASE INHIBITORS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MODELS, MOLECULAR; PROTEIN INTERACTION DOMAINS AND MOTIFS;

EID: 78650317971     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102420b     Document Type: Article

References (31)

1. Fletcher, S.; Hamilton, A. D. Curr. Opin. Chem. Biol. 2005, 9, 632
2. Peczuh, M. W.; Hamilton, A. D. Chem. Rev. 2000, 100, 2479
3. Zhou, H.; Wang, D. A.; Baldini, L.; Ennis, E.; Jain, R.; Carie, A.; Sebti, S. M.; Hamilton, A. Org. Biomol. Chem. 2006, 4, 2376
4. Park, H. S.; Lin, Q.; Hamilton, A. D. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5105
5. Blaskovich, M. A.; Lin, Q.; Delarue, F. L.; Sun, J.; Park, H. S.; Coppola, D.; Hamilton, A. D.; Sebti, S. M. Nat. Biotechnol. 2000, 18, 1065
6. Analogously, Liu and co-workers have recently shown that p -sulfonatocalix[ n ]arenes do not show toxic effects in mice poisoned with viologen derivatives. In addition, the mortality rate of viologen poisoned mice was significantly decreased
7. Wang, K.; Guo, D. S.; Zhang, H. Q.; Li, D.; Zheng, X. L.; Liu, Y. J. Med. Chem. 2009, 52, 6402
8. Francese, S.; Cozzolino, A.; Caputo, I.; Esposito, C.; Martino, M.; Gaeta, C.; Troisi, F.; Neri, P. Tetrahedron Lett. 2005, 46, 1611
9. Mecca, T.; Consoli, G. M. L.; Geraci, C.; La Spina, R.; Cunsolo, F. Org. Biomol. Chem. 2006, 4, 3763
10. Perret, F.; Lazar, A. N.; Coleman, A. W. Chem. Commun. 2006, 2425
11. Baldini, L.; Casnati, A.; Sansone, F.; Ungaro, R. Chem. Soc. Rev. 2007, 36, 254
12. Baylin, S. B.; Ohm, J. E. Nat. Rev. Cancer 2006, 6, 107
13. Xu, W. S.; Parmigiani, R. B.; Marks, P. A. Oncogene 2007, 26, 5541
14. Lund, A. H.; van Lohuizen, M. Genes Dev. 2004, 18, 2315
15. Witt, O.; Deubzer, H. E.; Milde, T.; Oehme, I. Cancer Lett. 2009, 277, 8
16. Bolden, J. E.; Peart, M. J.; Johnstone, R. W. Nat. Rev. Drug Discovery 2006, 5, 769
17. Yoo, C. B.; Jones, P. A. Nat. Rev. Drug Discovery 2006, 5, 37
18. Bieliauskas, A. V.; Pflum, M. K. Chem. Soc. Rev. 2008, 37, 1402
19. Marks, P. A.; Breslow, R. Nat. Biotechnol. 2007, 25, 84
20. Horne, W. S.; Olsen, C. A.; Beierle, J. M.; Montero, A.; Ghadiri, M. R. Angew. Chem., Int. Ed. 2009, 48, 4718
21. Wang, D.-F. Curr. Top. Med. Chem. 2009, 9, 241
22. Gutsche, C. D. Calixarenes, An Introduction; Royal Society of Chemistry: Cambridge, UK, 2008.
23. Wang, D.-F.; Wiest, O.; Helquist, P.; Lan-Hargest, H.-Y.; Wiech, N. L. J. Med. Chem. 2004, 47, 3409
24. Troisi, F.; Gaeta, C.; Pierro, T.; Neri, P. Tetrahedron Lett. 2009, 50, 5113
25. Troisi, F.; Russo, A.; Gaeta, C.; Bifulco, G.; Neri, P. Tetrahedron Lett. 2007, 48, 7986
26. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. J. Comput. Chem. 1998, 19, 1639
27. Finnin, M. S.; Donigian, J. R.; Cohen, A.; Richon, V. M.; Rifkind, R. A.; Marks, P. A.; Breslow, R.; Pavletich, N. P. Nature 1999, 401, 188
28. Nakao, Y.; Yoshida, S.; Matsunaga, S.; Shindoh, N.; Terada, Y.; Nagai, K.; Yamashita, J. K.; Ganesan, A.; van Soest, R. W.; Fusetani, N. Angew. Chem., Int. Ed. 2006, 45, 7553
29. See Supporting Information for further details.
30. Jakobi, R. A.; Böhmer, V.; Gruttner, C.; Kraft, D.; Vogt, W. New J. Chem. 1996, 20, 493
31. Saadioui, M.; Shivanyuk, A.; Böhmer, V.; Vogt, W. J. Org. Chem. 1999, 64, 3774