Design, synthesis and preliminary bioactivity studies of 1,2-dihydrobenzo[d]isothiazol-3-one-1,1-dioxide hydroxamic acid derivatives as novel histone deacetylase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 5, 2014, Pages 1529-1538

  Han, Leiqiang ^a   Wang, Lei ^a   Hou, Xuben ^a   Fu, Huansheng ^a   Song, Weiguo ^a   Tang, Weiping ^b   Fang, Hao ^a  

^a SHANDONG UNIVERSITY   (China)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

1,2 Dihydrobenzo d isothiazol 3 one 1,1 dioxide; Antiproliferative; Histone deacetylase inhibitor

Indexed keywords

1,2 DIHYDROBENZO[D]ISOTHIAZOL 3 ONE 1,1 DIOXIDE HYDROXAMIC ACID DERIVATIVE; 2 (1,1 DIOXIDO 3 OXOBENZO[D]ISOTHIAZOL 2(3H) YL)ACETIC ACID; 2 (6 NITRO 1,1 DIOXIDO 3 OXOBENZO[D]ISOTHIAZOL 2(3H) YL)ACETIC ACID; 3 (1,1 DIOXIDO 3 OXOBENZO[D]ISOTHIAZOL 2(3H) YL)PROPANOIC ACID; 3 (6 NITRO 1,1 DIOXIDO 3 OXOBENZO[D]ISOTHIAZOL 2(3H)YL)PROPANOIC ACID; 3 [1,1 DIOXIDO 3 OXO 6 (3,4,5TRIMETHOXYBENZAMIDO)[D]ISOTHIAZOL 2(3H)YL]PROPANOIC ACID; 3 [6 [(1,10 BIPHENYL) 4 YLCARBOXAMIDO] 1,1 DIOXIDO 3 OXOBENZO[D]ISOTHIAZOL 2(3H)YL]PROPANOIC ACID; 4 (1,1 DIOXIDO 3 OXOBENZO[D]ISOTHIAZOL 2(3H) YL)BUTANOIC ACID; 4 (6 NITRO 1,1 DIOXIDO 3 OXOBENZO[D]ISOTHIAZOL 2(3H) YL)BUTANOIC ACID; 5 (1,1 DIOXIDO 3 OXOBENZO[D]ISOTHIAZOL 2(3H) YL)PENTANOIC ACID; 5 (6 NITRO 1,1 DIOXIDO 3 OXOBENZO[D]ISOTHIAZOL 2(3H) YL)PENTANOIC ACID; 5 [6 BENZAMIDO 1,1 DIOXIDO 3 OXOBENZO[D]ISOTHIAZOL 2(3H)YL]PENTANOIC ACID; 6 (1,1 DIOXIDO 3 OXOBENZO[D]ISOTHIAZOL 2(3H) YL)HEXANOIC ACID; 6 (6 IODO 1,1 DIOXIDO 3 OXOBENZO[D]ISOTHIAZOL 2(3H) YL)HEXANOIC ACID; 6 (6 NITRO 1,1 DIOXIDO 3 OXOBENZO[D]ISOTHIAZOL 2(3H) YL)HEXANOIC ACID; 6 [1,1 DIOXIDO 3 OXO 6 (3,4,5 TRIMETHOXYBENZAMIDO)BENZO[D]ISOTHIAZOL 2(3H)YL]HEXANOIC ACID; 6 [6 (4 IODOBENZAMIDO) 1,1 DIOXIDO 3 OXOBENZO[D]ISOTHIAZOL 2(3H)YL]HEXANOIC ACID; 6 [6 (4 METHOXYBENZAMIDO) 1,1 DIOXIDO 3 OXOBENZO[D]ISOTHIAZOL 2(3H)YL]HEXANOIC ACID; 6 [6 [(1,10 BIPHENYL) 4 YLCARBOXAMIDO] 1,1 DIOXIDO 3 OXOBENZO[D]ISOTHIAZOL 2(3H)YL]HEXANOIC ACID; 6 [6 BENZAMIDO 1,1 DIOXIDO 3 OXOBENZO[D]ISOTHIAZOL 2(3H)YL]HEXANOIC ACID; ANTINEOPLASTIC AGENT; HISTONE DEACETYLASE; HISTONE DEACETYLASE INHIBITOR; HYDROXAMIC ACID DERIVATIVE; N [2 [6 (HYDROXYAMINO) 6 OXOHEXYL] 1,1 DIOXIDO 3 OXO 2,3 DIHYDROBENZO[D]ISOTHIAZOL 6 YL] 4 NITROBENZAMIDE; N [2 [6 (HYDROXYAMINO) 6 OXOHEXYL] 1,1 DIOXIDO 3 OXO 2,3 DIHYDROBENZO[D]ISOTHIAZOL 6 YL]BENZAMIDE; N [2 [6 (HYDROXYAMINO) 6 OXOHEXYL] 1,1 DIOXIDO 3 OXO 2,3 DIHYDROBENZO[D]ISOTHIAZOL 6 YL]THIOPHENE 2 CARBOXAMIDE; SACCHARIN HYDROXAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VORINOSTAT; HYDROXAMIC ACID;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG APPROVAL; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; CELL PROLIFERATION; CHEMISTRY; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CELL PROLIFERATION; DRUG DESIGN; HISTONE DEACETYLASE INHIBITORS; HISTONE DEACETYLASES; HYDROXAMIC ACIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84896706991     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.01.045     Document Type: Article

References (17)

1. A. Sato Onco. Targets Ther. 5 2012 67
2. W. Weichert Cancer Lett. 280 2009 168
3. B.E. Gryder, Q.H. Sodji, and A.K. Oyelere Future Med. Chem. 4 2012 505
4. V. Patil, Q.H. Sodji, J.R. Kornacki, M. Mrksich, and A.K. Oyelere J. Med. Chem. 56 2013 3492
5. J. Jiao, H. Fang, X. Wang, P. Guan, Y. Yuan, and W. Xu Eur. J. Med. Chem. 44 2009 4470
6. P. Guan, F. Sun, X. Hou, F. Wang, F. Yi, W. Xu, and H. Fang Bioorg. Med. Chem. 20 2012 3865
7. Y. Zhang, J. Feng, Y. Jia, X. Wang, L. Zhang, C. Liu, H. Fang, and W. Xu J. Med. Chem. 54 2011 2823
8. Y. Zhang, H. Fang, J. Feng, Y. Jia, X. Wang, and W. Xu J. Med. Chem. 54 2011 5532
9. Y. Zhang, J. Feng, C. Liu, L. Zhang, J. Jiao, H. Fang, L. Su, X. Zhang, J. Zhang, M. Li, B. Wang, and W. Xu Bioorg. Med. Chem. 18 2010 1761
10. H. Sommermeyer, R. Schreiber, J.M. Greuel, J. De Vry, and T. Glaser Eur. J. Pharmacol. 240 1993 29
11. J. Blanchet, T. Macklin, P. Ang, C. Metallinos, and V. Snieckus J. Org. Chem. 72 2007 3199
12. M.B. Youdim, and R. Ashkenazi Eur. J. Pharmacol. 119 1985 39
13. Gomez, Vidal, J. A.; Dominguez, Seglar, J. F.; Tabraue, Chavez, M. PCT Int. Appl. WO/2008/003800 A1.
14. K. Hiroyoshi, Y. Shuji, and N. Masato Bull. Chem. Soc. Jpn. 55 1982 3824
15. G.M. Morris, R. Huey, W. Lindstrom, M.F. Sanner, R.K. Belew, D.S. Goodsell, and A.J. Olson J. Comput. Chem. 30 2009 2785
16. E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, and T.E. Ferrin J. Comput. Chem. 25 2004 1605
17. Li, Z.; Mu, X.; Fan, Z.; Li, Y.; Liu, B. CN 200510013913.