메뉴 건너뛰기




Volumn 16, Issue 6, 2011, Pages 4681-4694

Synthetic routes and biological evaluation of largazole and its analogues as potent histone deacetylase inhibitors

Author keywords

Biological evaluation; Histone deacetylase inhibitor; Largazole; Natural products; Total synthesis

Indexed keywords

DEPSIPEPTIDE; HISTONE DEACETYLASE; HISTONE DEACETYLASE INHIBITOR; LARGAZOLE; THIAZOLE DERIVATIVE;

EID: 79959603291     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16064681     Document Type: Review
Times cited : (23)

References (21)
  • 1
    • 30344477367 scopus 로고    scopus 로고
    • Histone deacetylase inhibitors and the promise of epigenetic (and more) treatments for cancer
    • DOI 10.1038/nrc1779
    • Minucci, S.; Pelicci, P.G. Histone deacetylase inhibitors and the promise of epigenetic (and more) treatments for cancer. Nat. Rev. Cancer 2006, 6, 38-51. (Pubitemid 43054973)
    • (2006) Nature Reviews Cancer , vol.6 , Issue.1 , pp. 38-51
    • Minucci, S.1    Pelicci, P.G.2
  • 2
    • 39049135494 scopus 로고    scopus 로고
    • Structure and activity of largazole, a potent antiproliferative agent from the Floridian marine cyanobacterium Symploca sp
    • DOI 10.1021/ja7110064
    • Taori, K.; Paul, V.J.; Luesch, H. Structure and Activity of Largazole, a Potent Antiproliferative Agent from the Floridian Marine Cyanobacterium Symploca sp. J. Am. Chem. Soc. 2008, 130, 1806-1807. (Pubitemid 351238618)
    • (2008) Journal of the American Chemical Society , vol.130 , Issue.6 , pp. 1806-1807
    • Taori, K.1    Paul, V.J.2    Luesch, H.3
  • 3
    • 46049100010 scopus 로고    scopus 로고
    • Total synthesis and molecular target of largazole, a histone deacetylase inhibitor
    • DOI 10.1021/ja8013727
    • Ying, Y.; Taori, K.; Hong, J.; Luesch, H. Total Synthesis and Molecular Target of Largazole, a Histone Deacetylase Inhibitor. J. Am. Chem. Soc. 2008, 130, 8455-8459. (Pubitemid 351898566)
    • (2008) Journal of the American Chemical Society , vol.130 , Issue.26 , pp. 8455-8459
    • Ying, Y.1    Taori, K.2    Kim, H.3    Hong, J.4    Luesch, H.5
  • 4
    • 0000665968 scopus 로고
    • New C-4-chiral 1,3-thiazolidine-2-thiones: Excellent chiral auxiliaries for highly diastereo-controlled aldol-type reactions of acetic acid and alpha;, beta;-unsaturated aldehydes
    • Nagao, Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue, T.; Hashimoto, K.; Fujita, E. New C-4-chiral 1,3-thiazolidine-2-thiones: excellent chiral auxiliaries for highly diastereo-controlled aldol-type reactions of acetic acid and .alpha.,.beta.-unsaturated aldehydes. J. Org. Chem. 1986, 51, 2391-2393.
    • (1986) J. Org. Chem. , vol.51 , pp. 2391-2393
    • Nagao, Y.1    Hagiwara, Y.2    Kumagai, T.3    Ochiai, M.4    Inoue, T.5    Hashimoto, K.6    Fujita, E.7
  • 5
    • 4544234152 scopus 로고    scopus 로고
    • Stereoselective aldol additions of titanium enolates of N-acetyl-4-isopropyl-thiazolidinethione
    • DOI 10.1016/j.tet.2004.08.008, PII S004040200401292X
    • Hodge, M.B.; Olivo, H.F. Stereoselective aldol additions of titanium enolates of N-acetyl-4-isopropyl-thiazolidinethione. Tetrahedron 2004, 60, 9397-9403. (Pubitemid 39222135)
    • (2004) Tetrahedron , vol.60 , Issue.42 , pp. 9397-9403
    • Hodge, M.B.1    Olivo, H.F.2
  • 6
    • 55949094932 scopus 로고    scopus 로고
    • Synthesis and activity of largazole analogues with linker and macrocycle modification
    • Ying, Y.; Liu, Y.; Byeon, S.R.; Kim, H.; Luesch, H.; Hong, J. Synthesis and Activity of Largazole Analogues with Linker and Macrocycle Modification. Org. Lett. 2008, 10, 4021-4024.
    • (2008) Org. Lett. , vol.10 , pp. 4021-4024
    • Ying, Y.1    Liu, Y.2    Byeon, S.R.3    Kim, H.4    Luesch, H.5    Hong, J.6
  • 7
    • 52049119362 scopus 로고    scopus 로고
    • Synthesis and biological activity of largazole and derivatives
    • Seiser, T.; Kamena, F.; Cramer, N. Synthesis and Biological Activity of Largazole and Derivatives. Angew. Chem. Int. Ed. 2008, 47, 6483-6485.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 6483-6485
    • Seiser, T.1    Kamena, F.2    Cramer, N.3
  • 9
    • 0027513993 scopus 로고
    • Enantioselective Synthesis of 2-alkyl substituted cysteines
    • Pattenden, G.; Thom, S.M.; Jone, M.F. Enantioselective Synthesis of 2-alkyl substituted cysteines. Tetrahedron. 1993, 49, 2131-2138.
    • (1993) Tetrahedron. , vol.49 , pp. 2131-2138
    • Pattenden, G.1    Thom, S.M.2    Jone, M.F.3
  • 10
    • 55949099039 scopus 로고    scopus 로고
    • Enantioselective Total Synthesis of (+)-Largazole, a Potent Inhibitor of Histone Deacetylase
    • Ghosh, A.K.; Kulkarni, S. Enantioselective Total Synthesis of (+)-Largazole, a Potent Inhibitor of Histone Deacetylase. Org. Lett. 2008, 10, 3907-3909.
    • (2008) Org. Lett. , vol.10 , pp. 3907-3909
    • Ghosh, A.K.1    Kulkarni, S.2
  • 11
    • 0037414956 scopus 로고    scopus 로고
    • A biomimetic synthesis of thiazolines using hexaphenyloxodiphosphonium trifluoromethanesulfonate
    • DOI 10.1002/anie.200390059
    • You, S.L.; Razavi, H.; Kelly, J.W. A Biomimetic Synthesis of Thiazolines Using Hexaphenyloxodiphosphonium Trifluoromethanesulfonate. Angew. Chem. Int. Ed. 2003, 42, 83-85. (Pubitemid 36109504)
    • (2003) Angewandte Chemie - International Edition , vol.42 , Issue.1 , pp. 83-85
    • You, S.-L.1    Razavi, H.2    Kelly, J.W.3
  • 12
    • 54149114729 scopus 로고    scopus 로고
    • Total synthesis of largazole and its biological evaluation
    • Numajiri, Y.; Takahashi, T.; Takagi, M.; Shin-ya, K.; Doi, T. Total Synthesis of Largazole and Its Biological Evaluation. Synlett 2008, 16, 2483-2486.
    • (2008) Synlett , vol.16 , pp. 2483-2486
    • Numajiri, Y.1    Takahashi, T.2    Takagi, M.3    Shin-ya, K.4    Doi, T.5
  • 13
    • 19544377371 scopus 로고    scopus 로고
    • Molybdenum oxides as highly effective dehydrative cyclization catalysts for the synthesis of oxazolines and thiazolines
    • DOI 10.1021/ol050543j
    • Sakakura, A.; Kondo, R.; Ishihara, K. Molybdenum Oxides as Highly Effective Dehydrative Cyclization Catalysts for the Synthesis of Oxazolines and Thiazolines. Org. Lett. 2005, 7, 1971-1974. (Pubitemid 40732026)
    • (2005) Organic Letters , vol.7 , Issue.10 , pp. 1971-1974
    • Sakakura, A.1    Kondo, R.2    Ishihara, K.3
  • 14
    • 39749135372 scopus 로고    scopus 로고
    • Indene-based thiazolidinethione chiral auxiliary for propionate and acetate aldol additions
    • Osorio-Lozada, A.; Olivo, H.F. Indene-Based Thiazolidinethione Chiral Auxiliary for Propionate and Acetate Aldol Additions. Org. Lett. 2008, 10, 617-620.
    • (2008) Org. Lett. , vol.10 , pp. 617-620
    • Osorio-Lozada, A.1    Olivo, H.F.2
  • 15
    • 54049152858 scopus 로고    scopus 로고
    • A concise total synthesis of largazole, solution structure, and some preliminary structure activity relationships
    • Nasveschuk, C.G.; Ungermannova, D.; Liu, X.; Phillips, A.J. A Concise Total Synthesis of Largazole, Solution Structure, and Some Preliminary Structure Activity Relationships. Org. Lett. 2008, 10, 3595-3598.
    • (2008) Org. Lett. , vol.10 , pp. 3595-3598
    • Nasveschuk, C.G.1    Ungermannova, D.2    Liu, X.3    Phillips, A.J.4
  • 16
    • 85027471088 scopus 로고
    • Ueber den eintritt der halogene in das molekül des acetessigthers
    • Hantzsch, A. Ueber den Eintritt der Halogene in das Molekül des Acetessigthers. Chem. Ber. 1890, 23, 2339-2342.
    • (1890) Chem. Ber. , vol.23 , pp. 2339-2342
    • Hantzsch, A.1
  • 17
    • 70449396598 scopus 로고    scopus 로고
    • Total synthesis of largazole - Devolution of a novel synthetic strategy
    • Wang, B.; Forsyth, C.J. Total Synthesis of Largazole - Devolution of a Novel Synthetic Strategy. Synthesis 2009, 17, 2873-2880.
    • (2009) Synthesis , vol.17 , pp. 2873-2880
    • Wang, B.1    Forsyth, C.J.2
  • 18
    • 50249144006 scopus 로고    scopus 로고
    • Total synthesis and biological mode of action of largazole: A potent class i histone deacetylase inhibitor
    • Bowers, A.; West, N.; Taunton, J.; Schreiber, S.L.; Bradner, J.E.; Williams, R.M. Total Synthesis and Biological Mode of Action of Largazole: A Potent Class I Histone Deacetylase Inhibitor. J. Am. Chem. Soc. 2008, 130, 11219-11222.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 11219-11222
    • Bowers, A.1    West, N.2    Taunton, J.3    Schreiber, S.L.4    Bradner, J.E.5    Williams, R.M.6
  • 19
    • 64049106355 scopus 로고    scopus 로고
    • Synthesis and histone deacetylase inhibitory activity of largazole analogs: Alteration of the zinc-binding domain and macrocyclic scaffold
    • Bowers, A.A.; West, N.; Newkirk, T.L.; Youngman, A.E.; Schreiber, S.L.; Wiest, O.; Bradner, J.E.; Williams, R.M. Synthesis and Histone Deacetylase Inhibitory Activity of Largazole Analogs: Alteration of the Zinc-Binding Domain and Macrocyclic Scaffold. Org. Lett. 2009, 11, 1301-1304.
    • (2009) Org. Lett. , vol.11 , pp. 1301-1304
    • Bowers, A.A.1    West, N.2    Newkirk, T.L.3    Youngman, A.E.4    Schreiber, S.L.5    Wiest, O.6    Bradner, J.E.7    Williams, R.M.8
  • 21
    • 77949831890 scopus 로고    scopus 로고
    • Total synthesis and biological evaluation of largazole and derivatives with promising selectivity for cancers cells
    • Zeng, X.; Yin, B.; Hu, Z.; Liao, C.; Liu, J.; Li, S.; Li, Z.; Niclaus, M.C.; Zhou, G.; Jiang, S. Total Synthesis and Biological Evaluation of Largazole and Derivatives with Promising Selectivity for Cancers Cells. Org. Lett. 2010, 12, 1368-1371.
    • (2010) Org. Lett. , vol.12 , pp. 1368-1371
    • Zeng, X.1    Yin, B.2    Hu, Z.3    Liao, C.4    Liu, J.5    Li, S.6    Li, Z.7    Niclaus, M.C.8    Zhou, G.9    Jiang, S.10


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.