Design, synthesis, and biological evaluation of novel histone deacetylase 1 inhibitors through click chemistry

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 11, 2013, Pages 3295-3299

  Sun, Qiao ^a   Yao, Yiwu ^a   Liu, Chunping ^a   Li, Hua ^a   Yao, Hequan ^b   Xue, Xiaowen ^b   Liu, Jinsong ^a   Tu, Zhengchao ^a   Jiang, Sheng ^a  

^a GUANGZHOU INSTITUTES OF BIOMEDICINE AND HEALTH   (China)

^b CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Click chemistry; HDAC inhibitors; Molecular docking; Structure activity relationship; Suberoylanilide hydroxamic acid (SAHA)

Indexed keywords

ANTINEOPLASTIC AGENT; HISTONE DEACETYLASE 1; HISTONE DEACETYLASE 1 INHIBITOR; HISTONE DEACETYLASE 7; HISTONE DEACETYLASE INHIBITOR; UNCLASSIFIED DRUG; VORINOSTAT;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BINDING AFFINITY; CANCER CELL CULTURE; CANCER GROWTH; CELL MEDIATED CYTOTOXICITY; CLICK CHEMISTRY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; IC 50; IN VITRO STUDY; MOLECULAR MODEL;

ANTINEOPLASTIC AGENTS; BINDING SITES; CATALYTIC DOMAIN; CELL LINE; CELL PROLIFERATION; CLICK CHEMISTRY; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; DRUG SCREENING ASSAYS, ANTITUMOR; HISTONE DEACETYLASE 1; HISTONE DEACETYLASE INHIBITORS; HISTONE DEACETYLASES; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; HUMANS; HYDROXAMIC ACIDS; MOLECULAR DOCKING SIMULATION; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84877577635     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2013.03.102     Document Type: Article

References (29)

1. C.B. Yoo, and P.A. Jones Nat. Rev. Drug Discovery 5 2006 37
2. E. Verdin, F. Dequiedt, and H. Kasler Trends Genet. 19 2003 286
3. B.E. Bernstein, J.K. Tong, and S.L. Schreiber Proc. Natl. Acad. Sci. U.S.A. 97 2000 13708
4. R.W. Johnstone Nature Rev. Drug Discovery 1 2002 287
5. M. Dokmanovic, C. Clarke, and P.A. Marks Mol. Cancer Res. 5 2007 981
6. A.J. de Ruijter, A.H. van Gennip, H.N. Caron, S. Kemp, and A.B. van Kuilenburg Biochem. J. 370 2003 737
7. W. Weichert, A. Röske, V. Gekeler, T. Beckers, C. Stephan, K. Jung, F.R. Fritzsche, S. Niesporek, C. Denkert, M. Dietel, and G. Kristiansen Br. J. Cancer 98 2008 604
8. W. Weichert, A. Röske, S. Niesporek, A. Noske, A.-C. Buckendahl, M. Dietel, V. Gekeler, M. Boehm, T. Beckers, and C. Denkert Clin. Cancer Res. 14 2008 1669
9. T. Rikimaru, A. Taketomi, Y. Yamashita, K. Shirabe, T. Hamatsu, M. Shimada, and Y. Maehara Oncology 72 2007 69
10. K. Miyake, T. Yoshizumi, S. Imura, K. Sugimoto, E. Batmunkh, H. Kanemura, Y. Morine, and M. Shimada Pancreas 36 2008 e1
11. S. Ropero, and M. Esteller Mol. Oncol. 1 2007 19
12. A.A. Lane, and B.A.J. Chabner Clin. Oncol. 27 2009 5459
13. S. Grant, C. Easley, and P. Kirkpatrick Nat. Rev. Drug Discovery 6 2007 21
14. S. Minucci, and P.G. Pelicci Nat. Rev. Cancer 6 2006 38
15. T.C. Karagiannis, and A. El-Osta Leukemia 21 2007 61
16. M. Paris, M. Porcelloni, M. Binaschi, and D. Fattori J. Med. Chem. 51 2008 1505
17. C.H. Arrowsmith, C. Bountra, P.V. Fish, K. Lee, and M. Schapira Nat. Rev. Drug Discovery 11 2012 384
18. O. Bruserud, C. Stapnes, E. Ersvaer, B.T. Gjertsen, and A. Ryningen Curr. Pharm. Biotechnol. 8 2007 388
19. A.P. Kozikowski, S. Tapadar, D.N. Luchini, K.H. Kim, and D.D.J. Billadeau J. Med. Chem. 51 2008 4370
20. C. Salmi-Smail, A. Fabre, F. Dequiedt, A. Restouin, R. Castellano, S. Garbit, P. Roche, X. Morelli, J.M. Brunel, and Y.J. Collette J. Med. Chem. 53 2010 3038
21. Y. Zhang, H. Fang, J. Feng, Y. Jia, X. Wang, and W.J. Xu J. Med. Chem. 54 2011 5532
22. D. Moffat, S. Patel, F. Day, A. Belfield, A. Donald, M. Rowlands, J. Wibawa, D. Brotherton, L. Stimson, V. Clark, J. Owen, L. Bawden, G. Box, E. Bone, P. Mortenson, A. Hardcastle, S. van Meurs, S. Eccles, F. Raynaud, and W.J. Aherne J. Med. Chem. 53 2010 8663
23. X. Zeng, B. Yin, Z. Hu, C. Liao, J. Liu, S. Li, Z. Li, M.C. Nicklaus, G. Zhou, and S. Jiang Org. Lett. 12 2010 1368
24. X. Li, Z. Tu, H. Li, C. Liu, Z. Li, Q. Sun, Y. Yao, J. Liu, and S. Jiang ACS Med. Chem. Lett. 4 2013 132
25. P.C. Chen, V. Patil, W. Guerrant, P. Green, and A.K. Oyelere Bioorg. Med. Chem. 16 2008 4839
26. W.G. Lewis, L.G. Green, F. Grynszpan, Z. Radic, P.R. Carlier, P. Taylor, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 1053
27. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2596
28. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004
29. S.P. Pedersen, and A. Abell Eur. J. Org. Chem. 2011 2399