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Volumn 46, Issue 11, 2011, Pages 5387-5397

Design, synthesis and primary activity assay of tripeptidomimetics as histone deacetylase inhibitors with linear linker and branched cap group

Author keywords

1,4 Dithia 7 azaspiro 4,4 nonane 8 carboxylic acid derivatives; Histone deacetylases; Inhibitor; Synthesis

Indexed keywords

6 [7 (2 (TERT BUTOXYCARBONYLAMINO)ACETYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXAMIDO]HEXANOIC ACID; 6 [7 (2 (TERT BUTOXYCARBONYLAMINO)BUTANOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXAMIDO]HEXANOIC ACID; 6 [7 (3 (TERT BUTOXYCARBONYLAMINO)PROPANOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXAMIDO]HEXANOIC ACID; 6 [7 (4 (TERT BUTOXYCARBONYLAMINO)BUTANOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXAMIDO]HEXANOIC ACID; 7 (TERT BUTOXYCARBONYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXYLIC ACID; HISTONE DEACETYLASE INHIBITOR; HYDROXAMIC ACID DERIVATIVE; METHYL 6 (1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXAMIDO)HEXANOATE; METHYL 6 [7 (2 (TERT BUTOXYCARBONYLAMINO) 3 (1H INDOL 3 YL)PROPANOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXAMIDO]HEXANOATE; METHYL 6 [7 (2 (TERT BUTOXYCARBONYLAMINO) 3 (4 HYDROXYPHENYL)PROPANOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXAMIDO]HEXANOATE; METHYL 6 [7 (2 (TERT BUTOXYCARBONYLAMINO) 3 HYDROXYPROPANOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXAMIDO]HEXANOATE; METHYL 6 [7 (2 (TERT BUTOXYCARBONYLAMINO) 3 METHYLBUTANOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXAMIDO]HEXANOATE; METHYL 6 [7 (2 (TERT BUTOXYCARBONYLAMINO) 3 METHYLPENTANOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXAMIDO]HEXANOATE; METHYL 6 [7 (2 (TERT BUTOXYCARBONYLAMINO) 3 PHENYLPROPANOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXAMIDO]HEXANOATE; METHYL 6 [7 (2 (TERT BUTOXYCARBONYLAMINO) 4 METHYLPENTANOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXAMIDO]HEXANOATE; METHYL 6 [7 (2 (TERT BUTOXYCARBONYLAMINO)ACETYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXAMIDO]HEXANOATE; METHYL 6 [7 (2 (TERT BUTOXYCARBONYLAMINO)HEXANOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXAMIDO]HEXANOATE; METHYL 6 [7 (2 (TERT BUTOXYCARBONYLAMINO)PROPANOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXAMIDO]HEXANOATE; METHYL 6 [7 (3 (TERT BUTOXYCARBONYLAMINO)PROPANOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXAMIDO]HEXANOATE; METHYL 6 [7 (4 (TERT BUTOXYCARBONYLAMINO)BUTANOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXAMIDO]HEXANOATE; METHYL 6 AMINOHEXANOATE HYDROCHLORIDE; N(6 (HYDROXYAMINO) 6 OXOHEXYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXAMIDE HYDROCHLORIDE; TERT BUTYL 1 [8 (6 (HYDROXYAMINO) 6 OXOHEXYLCARBAMOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONAN 7 YL] 1 OXO 3 PHENYLPROPAN 2 YLCARBAMATE; TERT BUTYL 1E[8 (6 (HYDROXYAMINO) 6 OXOHEXYLCARBAMOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONAN 7 YL] 3 (4 HYDROXYPHENYL) 1 OXOPROPAN 2 YLCARBAMATE; TERT BUTYL 2 [8 (6 METHOXY 6 OXOHEXYLCARBAMOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 7 CARBONYL]PYRROLIDINE 1 CARBOXYLATE; TERT BUTYL 4 [8 (6 METHOXY 6 OXOHEXYLCARBAMOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 7 CARBONYL]PIPERIDINE 1 CARBOXYLATE; TERT BUTYL 8 (6 METHOXY 6 OXOHEXYLCARBAMOYL) 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 7 CARBOXYLATE; TERT BUTYL 8 [6 (HYDROXYAMINO) 6 OXOHEXYLCARBAMOYL] 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 7 CARBOXYLATE; TRIPEPTIDOMIMETIC; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 80054921479     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.08.045     Document Type: Article
Times cited : (25)

References (37)
  • 1
    • 0031244521 scopus 로고    scopus 로고
    • Nuclear histone acetylases and deacetylases and transcriptional regulation: HATs off to HDACs
    • C.A. Hassig, and S.L. Schreiber Nuclear histone acetylases and deacetylases and transcriptional regulation: HATs off to HDACs Curr. Opin. Chem. Biol. 1 1997 300 308 (Pubitemid 127437155)
    • (1997) Current Opinion in Chemical Biology , vol.1 , Issue.3 , pp. 300-308
    • Hassig, C.A.1    Schreibert, S.L.2
  • 2
    • 0033000990 scopus 로고    scopus 로고
    • Histone acetylases and deacetylases in cell proliferation
    • DOI 10.1016/S0959-437X(99)80006-9
    • T. Kouzarides Histone acetylases and deacetylases in cell proliferation Curr. Opin. Genet. Dev. 9 1999 40 48 (Pubitemid 29080385)
    • (1999) Current Opinion in Genetics and Development , vol.9 , Issue.1 , pp. 40-48
    • Kouzarides, T.1
  • 3
    • 0029869172 scopus 로고    scopus 로고
    • Histone deacetylase: A regulator of transcription
    • DOI 10.1126/science.272.5260.371
    • A.P. Wolffe Histone deacetylase: a regulator of transcription Science 272 1996 371 372 (Pubitemid 26138173)
    • (1996) Science , vol.272 , Issue.5260 , pp. 371-372
    • Wolffe, A.P.1
  • 4
    • 36048958965 scopus 로고    scopus 로고
    • Histone deacetylase inhibitors: Overview and perspectives
    • DOI 10.1158/1541-7786.MCR-07-0324
    • M. Dokmanovic, C. Clarke, and P.A. Marks Histone deacetylase inhibitors: overview and perspectives Mol. Cancer Res. 5 2007 981 989 (Pubitemid 350080267)
    • (2007) Molecular Cancer Research , vol.5 , Issue.10 , pp. 981-989
    • Dokmanovic, M.1    Clarke, C.2    Marks, P.A.3
  • 5
    • 34248631385 scopus 로고    scopus 로고
    • The role of histone deacetylases (HDACs) in human cancer
    • DOI 10.1016/j.molonc.2007.01.001, PII S1574789107000026
    • S. Ropero, and M. Esteller The role of histone deacetylases (HDACs) in human cancer Mol. Oncol. 1 2007 19 25 (Pubitemid 46776612)
    • (2007) Molecular Oncology , vol.1 , Issue.1 , pp. 19-25
    • Ropero, S.1    Esteller, M.2
  • 7
    • 28044471827 scopus 로고    scopus 로고
    • Acetylation and deacetylation of non-histone proteins
    • DOI 10.1016/j.gene.2005.09.010, PII S037811190500572X
    • M.A. Glozak, N. Sengupta, X.H. Zhang, and E. Seto Acetylation and deacetylation of non-histone proteins Gene 363 2005 15 23 (Pubitemid 41691888)
    • (2005) Gene , vol.363 , Issue.1-2 , pp. 15-23
    • Glozak, M.A.1    Sengupta, N.2    Zhang, X.3    Seto, E.4
  • 8
    • 1842631408 scopus 로고    scopus 로고
    • Upregulation and Nuclear Recruitment of HDACl in Hormone Refractory Prostate Cancer
    • DOI 10.1002/pros.20022
    • K. Halkidou, L. Gaughan, S. Cook, H.Y. Leung, D.E. Neal, and C.N. Robson Upregulation and nuclear recruitment of HDAC1 in hormone refractory prostate cancer Prostate 59 2004 177 189 (Pubitemid 38481229)
    • (2004) Prostate , vol.59 , Issue.2 , pp. 177-189
    • Halkidou, K.1    Gaughan, L.2    Cook, S.3    Leung, H.Y.4    Neal, D.E.5    Robson, C.N.6
  • 12
    • 2342603414 scopus 로고    scopus 로고
    • Induction of HDAC2 expression upon loss of APC in colorectal tumorigenesis
    • DOI 10.1016/S1535-6108(04)00114-X, PII S153561080400114X
    • P. Zhu, E. Martin, J. Mengwasser, P. Schlag, K.P. Janssen, and M. Gottlicher Induction of HDAC2 expression upon loss of APC in colorectal tumorigenesis Cancer Cell. 5 2004 455 463 (Pubitemid 38610247)
    • (2004) Cancer Cell , vol.5 , Issue.5 , pp. 455-463
    • Zhu, P.1    Martin, E.2    Mengwasser, J.3    Schlag, P.4    Janssen, K.-P.5    Gottlicher, M.6
  • 16
    • 55749103404 scopus 로고    scopus 로고
    • Histone deacetylation: An attractive target for cancer therapy?
    • A. Al-Janadi, S.R. Chandana, and B.A. Cloney Histone deacetylation: an attractive target for cancer therapy? Drugs R&D 9 2008 369 383
    • (2008) Drugs R&D , vol.9 , pp. 369-383
    • Al-Janadi, A.1    Chandana, S.R.2    Cloney, B.A.3
  • 20
    • 33846122993 scopus 로고    scopus 로고
    • Dimethyl sulfoxide to vorinostat: Development of this histone deacetylase inhibitor as an anticancer drug
    • DOI 10.1038/nbt1272, PII NBT1272
    • P.A. Marks, and R. Breslow Dimethyl sulfoxide to vorinostat: development of this histone deacetylase inhibitor as an anticancer drug Nat. Biotechnol. 25 2007 84 90 (Pubitemid 46087907)
    • (2007) Nature Biotechnology , vol.25 , Issue.1 , pp. 84-90
    • Marks, P.A.1    Breslow, R.2
  • 21
    • 77749309291 scopus 로고    scopus 로고
    • Romidepsin for the treatment of cutaneous T-cell lymphoma
    • C. Campas-Moya Romidepsin for the treatment of cutaneous T-cell lymphoma Drugs Today (Barc) 45 2009 787 795
    • (2009) Drugs Today (Barc) , vol.45 , pp. 787-795
    • Campas-Moya, C.1
  • 22
    • 58149378600 scopus 로고    scopus 로고
    • The structure and function of histone deacetylases: The target for anti-cancer therapy
    • Y. Zhang, H. Fang, J. Jiao, and W. Xu The structure and function of histone deacetylases: the target for anti-cancer therapy Curr. Med. Chem. 15 2008 2840 2849
    • (2008) Curr. Med. Chem. , vol.15 , pp. 2840-2849
    • Zhang, Y.1    Fang, H.2    Jiao, J.3    Xu, W.4
  • 24
    • 77249167010 scopus 로고    scopus 로고
    • Design, synthesis and preliminary activity assay of 1,2,3,4- tetrahydroisoquinoline-3-carboxylic acid derivatives as novel Histone deacetylases (HDACs) inhibitors
    • 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 Design, synthesis and preliminary activity assay of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives as novel Histone deacetylases (HDACs) inhibitors Bioorg. Med. Chem. 18 2010 1761 1772
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 1761-1772
    • Zhang, Y.1    Feng, J.2    Liu, C.3    Zhang, L.4    Jiao, J.5    Fang, H.6    Su, L.7    Zhang, X.8    Zhang, J.9    Li, M.10    Wang, B.11    Xu, W.12
  • 25
    • 79955455755 scopus 로고    scopus 로고
    • Development of tetrahydroisoquinoline-based hydroxamic acid derivatives: Potent histone deacetylase inhibitors with marked in vitro and in vivo antitumor activities
    • Y. Zhang, J. Feng, Y. Jia, X. Wang, L. Zhang, C. Liu, H. Fang, and W. Xu Development of tetrahydroisoquinoline-based hydroxamic acid derivatives: potent histone deacetylase inhibitors with marked in vitro and in vivo antitumor activities J. Med. Chem. 54 2011 2823 2838
    • (2011) J. Med. Chem. , vol.54 , pp. 2823-2838
    • Zhang, Y.1    Feng, J.2    Jia, Y.3    Wang, X.4    Zhang, L.5    Liu, C.6    Fang, H.7    Xu, W.8
  • 26
    • 79960560741 scopus 로고    scopus 로고
    • Design, synthesis and biological evaluation of tyrosine-based hydroxamic acid analogs as novel histone deacetylases (HDACs) inhibitors
    • Y. Zhang, J. Feng, C. Liu, H. Fang, and W. Xu Design, synthesis and biological evaluation of tyrosine-based hydroxamic acid analogs as novel histone deacetylases (HDACs) inhibitors Bioorg. Med. Chem. 19 2011 4437 4444
    • (2011) Bioorg. Med. Chem. , vol.19 , pp. 4437-4444
    • Zhang, Y.1    Feng, J.2    Liu, C.3    Fang, H.4    Xu, W.5
  • 29
    • 61849144810 scopus 로고    scopus 로고
    • HDAC family: What are the cancer relevant targets?
    • O. Witt, H.E. Deubzer, T. Milde, and I. Oehme HDAC family: what are the cancer relevant targets? Cancer Lett. 277 2009 8 21
    • (2009) Cancer Lett. , vol.277 , pp. 8-21
    • Witt, O.1    Deubzer, H.E.2    Milde, T.3    Oehme, I.4
  • 30
    • 43749109171 scopus 로고    scopus 로고
    • A novel histone deacetylase 8 (HDAC8)-specific inhibitor PCI-34051 induces apoptosis in T-cell lymphomas
    • DOI 10.1038/leu.2008.9, PII LEU20089
    • S. Balasubramanian, J. Ramos, W. Luo, M. Sirisawad, E. Verner, and J.J. Buggy A novel histone deacetylase 8 (HDAC8)-specific inhibitor PCI-34051 induces apoptosis in T-cell lymphomas Leukemia 22 2008 1026 1034 (Pubitemid 351689885)
    • (2008) Leukemia , vol.22 , Issue.5 , pp. 1026-1034
    • Balasubramanian, S.1    Ramos, J.2    Luo, W.3    Sirisawad, M.4    Verner, E.5    Buggy, J.J.6
  • 31
    • 34247376560 scopus 로고    scopus 로고
    • Design and evaluation of 'Linkerless' hydroxamic acids as selective HDAC8 inhibitors
    • DOI 10.1016/j.bmcl.2007.02.064, PII S0960894X07002612
    • K. KrennHrubec, B.L. Marshall, M. Hedglin, E. Verdin, and S.M. Ulrich Design and evaluation of 'Linkerless' hydroxamic acids as selective HDAC8 inhibitors Bioorg. Med. Chem. Lett. 17 2007 2874 2878 (Pubitemid 46636249)
    • (2007) Bioorganic and Medicinal Chemistry Letters , vol.17 , Issue.10 , pp. 2874-2878
    • KrennHrubec, K.1    Marshall, B.L.2    Hedglin, M.3    Verdin, E.4    Ulrich, S.M.5
  • 34
    • 79960182729 scopus 로고    scopus 로고
    • Design, synthesis, docking, and biological evaluation of novel diazide-containing isoxazole- and pyrazole-based histone deacetylase probes
    • R. Neelarapu, D.L. Holzie, S. Velaparthi, H. Bai, M. Brunsteiner, S.Y. Blond, and P.A. Petukhov Design, synthesis, docking, and biological evaluation of novel diazide-containing isoxazole- and pyrazole-based histone deacetylase probes J. Med. Chem. 54 2011 4350 4364
    • (2011) J. Med. Chem. , vol.54 , pp. 4350-4364
    • Neelarapu, R.1    Holzie, D.L.2    Velaparthi, S.3    Bai, H.4    Brunsteiner, M.5    Blond, S.Y.6    Petukhov, P.A.7
  • 37
    • 68149119171 scopus 로고    scopus 로고
    • SAR studies on azasterols as potential anti-trypanosomal and anti-leishmanial agents
    • F. Gigante, M. Kaiser, R. Brun, and I.H. Gilbert SAR studies on azasterols as potential anti-trypanosomal and anti-leishmanial agents Bioorg. Med. Chem. 17 2009 5950 5961
    • (2009) Bioorg. Med. Chem. , vol.17 , pp. 5950-5961
    • Gigante, F.1    Kaiser, M.2    Brun, R.3    Gilbert, I.H.4


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