메뉴 건너뛰기




Volumn 60, Issue , 2013, Pages 410-420

Fragment-based design, synthesis, and biological evaluation of N-substituted-5-(4-isopropylthiophenol)-2-hydroxynicotinamide derivatives as novel Mcl-1 inhibitors

Author keywords

Apoptosis; FQ; Fragment based; LE; Mcl 1

Indexed keywords

1 BENZYL 5 (4 ISOPROPYLPHENYLTHIO) 2 OXO 1,2 DIHYDROPYRIDNE 3 CARBONITRILE; 2 CHLORONICOTINIC ACID; 2 CHLORONICOTINOYLCHLORIDE; 2 HYDROXYNICOTINONITRILE; 3 THIOMORPHOLIN 8OXO 8H ACENAPHTHO [1,2 B] PYRROLE 9 CARBONITRILE; 4 [4 (4' CHLORO 2 BIPHENYLYLMETHYL) 1 PIPERAZINYL] N [4 [3 DIMETHYLAMINO 1 (PHENYLTHIOMETHYL)PROPYLAMINO] 3 NITROBENZENESULFONYL]BENZAMIDE; 4 METHOXY 2 HYDROXYNICOTINONITRILE; 5 (4 AMINOPHENYLTHIO) 2 HYDROXYNICOTINONITRILE; 5 (4 BIPHENYL) 2 HYDROXYNICOTINONITRILE; 5 (4 BROMOPHENYLTHIO) 2 HYDROXYNICOTINONITRILE; 5 (4 CHLOROPHENYL) 2 HYDROXYNICOTINONITRILE; 5 (4 ISOPROPYLTHIOPHENOL) 2 HYDROXYNICOTINONITRILE; 5 (4 METHYLTHIOPHENOL) 2 HYDROXYNICOTINONITRILE; 5 (4 TERT AMYLTHIOPHENOL) 2 HYDROXYNICOTINONITRILE; 5 BROMO 2 HYDROXYNICOTINONITRILE; 5 NAPHTHYL 2 HYDROXYNICOTINONITRILE; 5 PHENYL 2 HYDROXYNICOTINONITRILE; 5 PHENYLTHIO 2 HYDROXYNICOTINONITRILE; MCL 1 INHIBITOR; N BENZYL 2 CHLORONICOTINAMIDE; N BENZYL 5 BROMO 2 HYDROXYNICOTINAMIDE; N BUTYL 2 CHLORONICOTINAMIDE; N BUTYL 5 BROMO 2 HYDROXYNICOTINAMIDE; N ISOPROPYL 2 CHLORONICOTINAMIDE; N ISOPROPYL 5 BROMO 2 HYDROXYNICOTINAMIDE; N PHENYLPROPYL 2 CHLORONICOTINAMIDE; NICOTINAMIDE DERIVATIVE; PROTEIN INHIBITOR; PROTEIN MCL 1; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 84872167041     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.12.016     Document Type: Article
Times cited : (26)

References (33)
  • 1
    • 0032575688 scopus 로고    scopus 로고
    • The Bcl-2 protein family: Arbiters of cell survival
    • J.M. Adams, and S. Cory The Bcl-2 protein family: arbiters of cell survival Science 281 1998 1322 1326
    • (1998) Science , vol.281 , pp. 1322-1326
    • Adams, J.M.1    Cory, S.2
  • 2
    • 0031918223 scopus 로고    scopus 로고
    • Bcl-2 family: Regulators of cell death
    • D.T. Chao, and S.J. Korsmeyer Bcl-2 family: regulators of cell death Annu. Rev. Immunol. 16 1998 395 419
    • (1998) Annu. Rev. Immunol. , vol.16 , pp. 395-419
    • Chao, D.T.1    Korsmeyer, S.J.2
  • 3
    • 0033491603 scopus 로고    scopus 로고
    • Recent progress on the regulation of apoptosis by Bcl-2 family members
    • A.J. Minn, R.E. Swain, A. Ma, and C.B. Thompson Recent progress on the regulation of apoptosis by Bcl-2 family members Adv. Immunol. 70 1998 245 279
    • (1998) Adv. Immunol. , vol.70 , pp. 245-279
    • Minn, A.J.1    Swain, R.E.2    Ma, A.3    Thompson, C.B.4
  • 4
    • 27544446991 scopus 로고    scopus 로고
    • Life in the balance: How BH3-only proteins induce apoptosis
    • S.N. Willis, and J.M. Adams Life in the balance: how BH3-only proteins induce apoptosis Curr. Opin. Cell. Biol. 17 2005 617 625
    • (2005) Curr. Opin. Cell. Biol. , vol.17 , pp. 617-625
    • Willis, S.N.1    Adams, J.M.2
  • 5
    • 42049091619 scopus 로고    scopus 로고
    • Unique biology of Mcl-1: Therapeutic opportunities in cancer
    • M.R. Warr, and G.C. Shore Unique biology of Mcl-1: therapeutic opportunities in cancer Curr. Mol. Med. 8 2008 138 147
    • (2008) Curr. Mol. Med. , vol.8 , pp. 138-147
    • Warr, M.R.1    Shore, G.C.2
  • 8
    • 79551485492 scopus 로고    scopus 로고
    • A novel BH3 mimetic S1 potently induces Bax/Bak-dependent apoptosis by targeting both Bcl-2 and Mcl-1
    • Z. Zhang, T. Song, T. Zhang, G. Wu, J. Gao, L. An, and G. Du A novel BH3 mimetic S1 potently induces Bax/Bak-dependent apoptosis by targeting both Bcl-2 and Mcl-1 Int. J. Cancer 128 2011 1724 1735
    • (2011) Int. J. Cancer , vol.128 , pp. 1724-1735
    • Zhang, Z.1    Song, T.2    Zhang, T.3    Wu, G.4    Gao, J.5    An, L.6    Du, G.7
  • 9
    • 79951847291 scopus 로고    scopus 로고
    • 3-thiomorpholin-8-oxo-8H-ace-naphtha [1,2-b]pyrrole-9-carbonitrile (S1) based molecules as potent, dual inhibitors of B-cell lymphoma 2 (Bcl-2) and myeloid cell leukemia sequence 1 (Mcl-1): Structure-based design and structure-activity relationship studies
    • Z. Zhang, G. Wu, F. Xie, T. Song, and X. Chang 3-thiomorpholin-8-oxo-8H- ace-naphtha [1,2-b]pyrrole-9-carbonitrile (S1) based molecules as potent, dual inhibitors of B-cell lymphoma 2 (Bcl-2) and myeloid cell leukemia sequence 1 (Mcl-1): structure-based design and structure-activity relationship studies J. Med. Chem. 4 2011 1101 1105
    • (2011) J. Med. Chem. , vol.4 , pp. 1101-1105
    • Zhang, Z.1    Wu, G.2    Xie, F.3    Song, T.4    Chang, X.5
  • 10
    • 33847381100 scopus 로고    scopus 로고
    • A decade of fragment-based drug design: Strategic advances and lessons learned
    • P.J. Hajduk, and J. Greer A decade of fragment-based drug design: strategic advances and lessons learned Nat. Rev. Drug Discov. 6 2007 211 219
    • (2007) Nat. Rev. Drug Discov. , vol.6 , pp. 211-219
    • Hajduk, P.J.1    Greer, J.2
  • 11
    • 36248997755 scopus 로고    scopus 로고
    • Fragment-based drug discovery: What has it achieved so far?
    • A.A. Alex, and M.M. Flocco Fragment-based drug discovery: what has it achieved so far? Curr. Top. Med. Chem. 7 2007 1544 1567
    • (2007) Curr. Top. Med. Chem. , vol.7 , pp. 1544-1567
    • Alex, A.A.1    Flocco, M.M.2
  • 12
    • 46849089254 scopus 로고    scopus 로고
    • Recent developments in fragment-based drug discovery
    • M. Congreve, G. Chessari, D. Tisi, and A.J. Woodhead Recent developments in fragment-based drug discovery J. Med. Chem. 51 2008 3661 3680
    • (2008) J. Med. Chem. , vol.51 , pp. 3661-3680
    • Congreve, M.1    Chessari, G.2    Tisi, D.3    Woodhead, A.J.4
  • 13
    • 67649341990 scopus 로고    scopus 로고
    • From fragment to clinical candidate-a historical perspective
    • G. Chessari, and A.J. Woodhead From fragment to clinical candidate-a historical perspective Drug Discov. Today 14 2009 668 675
    • (2009) Drug Discov. Today , vol.14 , pp. 668-675
    • Chessari, G.1    Woodhead, A.J.2
  • 14
    • 70349425790 scopus 로고    scopus 로고
    • Recent progress in fragment-based lead discovery
    • M.N. Schulz, and R.E. Hubbard Recent progress in fragment-based lead discovery Curr. Opin. Pharmacol. 9 2009 615 621
    • (2009) Curr. Opin. Pharmacol. , vol.9 , pp. 615-621
    • Schulz, M.N.1    Hubbard, R.E.2
  • 17
    • 33751204422 scopus 로고    scopus 로고
    • Fragment-based lead discovery: A chemical update
    • D.A. Erlanson Fragment-based lead discovery: a chemical update Curr. Opin. Biotechnol. 17 2006 643 652
    • (2006) Curr. Opin. Biotechnol. , vol.17 , pp. 643-652
    • Erlanson, D.A.1
  • 18
    • 1942453243 scopus 로고    scopus 로고
    • Ligand efficiency: A useful metric for lead selection
    • A.L. Hopkins, C.R. Groom, and A. Alex Ligand efficiency: a useful metric for lead selection Drug Discov. Today 9 2004 430 431
    • (2004) Drug Discov. Today , vol.9 , pp. 430-431
    • Hopkins, A.L.1    Groom, C.R.2    Alex, A.3
  • 19
    • 17044403086 scopus 로고    scopus 로고
    • Ligand efficiency indices as guide-posts for drug discovery
    • C. Abad-Zapatero, and J.T. Metz Ligand efficiency indices as guide-posts for drug discovery Drug Discov. Today 10 2005 464 469
    • (2005) Drug Discov. Today , vol.10 , pp. 464-469
    • Abad-Zapatero, C.1    Metz, J.T.2
  • 23
  • 24
    • 0029067387 scopus 로고
    • New synthetic routes to 3-, 5-, and 6-aryl-2-chloropyridine
    • R. Church, R. Trust, J.D. Albright, and D.W. Powell New synthetic routes to 3-, 5-, and 6-aryl-2-chloropyridine J. Org. Chem. 60 1995 3750 3758
    • (1995) J. Org. Chem. , vol.60 , pp. 3750-3758
    • Church, R.1    Trust, R.2    Albright, J.D.3    Powell, D.W.4
  • 25
    • 58849133301 scopus 로고    scopus 로고
    • Controlling the self assembly of arene functionalised 2-aminopyrimidines by arene-perfluoroarene interaction and by silver(I) complex formation
    • I. Stoll, R. Brodbeck, B. Neumann, H.G. Stammler, and J. Mattay Controlling the self assembly of arene functionalised 2-aminopyrimidines by arene-perfluoroarene interaction and by silver(I) complex formation Cryst. Eng. Commun. 11 2009 306 317
    • (2009) Cryst. Eng. Commun. , vol.11 , pp. 306-317
    • Stoll, I.1    Brodbeck, R.2    Neumann, B.3    Stammler, H.G.4    Mattay, J.5
  • 26
    • 19944432440 scopus 로고    scopus 로고
    • Synthesis and SAR of 5,6-diarylpyridines as human CB1 inverse agonists
    • L.C. Meurer, P.E. Finke, S.G. Mills, and T.F. Walsh Synthesis and SAR of 5,6-diarylpyridines as human CB1 inverse agonists Bioorg. Med. Chem. Lett. 15 2005 645 651
    • (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 645-651
    • Meurer, L.C.1    Finke, P.E.2    Mills, S.G.3    Walsh, T.F.4
  • 27
    • 0023212166 scopus 로고
    • 1,2-dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-6-methyl-2-oxo-3- pyridinecarbonitriles and related compounds synthesis and inotropic activity
    • B.L. Duell, J.A. Bristo1, R.E. Weishaar, and D.B. Evans 1,2-dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-6-methyl-2-oxo-3- pyridinecarbonitriles and related compounds synthesis and inotropic activity J. Med. Chem. 30 1987 1023 1029
    • (1987) J. Med. Chem. , vol.30 , pp. 1023-1029
    • Duell, B.L.1    Bristo, J.A.2    Weishaar, R.E.3    Evans, D.B.4
  • 28
    • 1242271305 scopus 로고    scopus 로고
    • Molecular recognition: The fragment approach in lead generation
    • D. Fattori Molecular recognition: the fragment approach in lead generation Drug Discov. Today 9 2004 229 238
    • (2004) Drug Discov. Today , vol.9 , pp. 229-238
    • Fattori, D.1
  • 29
    • 84859783234 scopus 로고    scopus 로고
    • Analysis of flexibility and hotspots in Bcl-xL and Mcl-1 proteins for the design of selective small-molecule inhibitors
    • doi:org/10.1021/ml200301w
    • C. Yang, and S. Wang Analysis of flexibility and hotspots in Bcl-xL and Mcl-1 proteins for the design of selective small-molecule inhibitors Med. Chem. Lett. 2012 doi:org/10.1021/ml200301w
    • (2012) Med. Chem. Lett.
    • Yang, C.1    Wang, S.2
  • 30
    • 41349123507 scopus 로고    scopus 로고
    • Bcl-2 dependence and ABT-737 sensitivity in acute lymphoblastic leukemia
    • Moore V. Del Gaizo, K.D. Schlis, S.E. Sallan, S.A. Armstrong, and A. Letai Bcl-2 dependence and ABT-737 sensitivity in acute lymphoblastic leukemia Blood 111 2008 2300 2309
    • (2008) Blood , vol.111 , pp. 2300-2309
    • Del Gaizo, M.V.1    Schlis, K.D.2    Sallan, S.E.3    Armstrong, S.A.4    Letai, A.5
  • 31
    • 20144388297 scopus 로고    scopus 로고
    • Identification of mcl-1 as a BCR-ABL-dependent target in chronic myeloid leukemia (CML): Evidence for cooperative antileukemic effects of imatinib and mcl-1 antisense oligonucleotides
    • K.J. Aichberger, M. Mayerhofer, M.T. Krauth, H. Skvara, S. Florian, K. Sonneck, C. Akgul, S. Derdak, and W.F. Pickl Identification of mcl-1 as a BCR-ABL-dependent target in chronic myeloid leukemia (CML): evidence for cooperative antileukemic effects of imatinib and mcl-1 antisense oligonucleotides Blood 105 2004 3303 3311
    • (2004) Blood , vol.105 , pp. 3303-3311
    • Aichberger, K.J.1    Mayerhofer, M.2    Krauth, M.T.3    Skvara, H.4    Florian, S.5    Sonneck, K.6    Akgul, C.7    Derdak, S.8    Pickl, W.F.9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.