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Volumn 9, Issue 9, 2014, Pages

Synthesis and characterization of novel 2-amino-chromene-nitriles that target Bcl-2 in acute myeloid leukemia cell lines

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 4 (1H INDOL 3 YL) 4H BENZO[G]CHROMENE 3 CARBONITRILE; 2 AMINO 4 (1H INDOL 3 YL) 5 OXO 4,5 DIHYDROPYRANO[3,2 C]CHROMENE 3 CARBONITRILE; 2 AMINO 4 (2 BUTYL 4 CHLORO 1H IMIDAZOL 5 YL) 4H BENZO[G]CHROMENE 3 CARBONITRILE; 2 AMINO 4 (2 BUTYL 4 CHLORO 1H IMIDAZOL 5 YL) 5 OXO 4,5 DIHYDROPYRANO[3,2 C]CHROMENE 3 CARBONITRILE; 2 AMINO 4 (2 BUTYL 4 CHLORO 1H IMIDAZOL 5 YL) 7 HYDROXY 4H CHROMENE 3 CARBONITRILE; 2 AMINO 4 (2 METHYL 1H INDOL 3 YL) 5 OXO 4,5 DIHYDROPYRANO[3,2 C]CHROMENE 3 CARBONITRILE; 2 AMINO 4 (2 NITROPHENYL) 4H BENZO[G]CHROMENE 3 CARBONITRILE; 2 AMINO 4 (2,6 DICHLOROPHENYL) 4H BENZO[G]CHROMENE 3 CARBONITRILE; 2 AMINO 4 (3 NITROPHENYL) 4H BENZO[G]CHROMENE 3 CARBONITRILE; 2 AMINO 4 (3,4 DIMETHOXYPHENYL) 5 OXO 4,5 DIHYDROPYRANO[3,2 C]CHROMENE 3 CARBONITRILE; 2 AMINO 4 (4 BROMOPHENYL) 4H BENZO[G]CHROMENE 3 CARBONITRILE; 2 AMINO 4 (4 BROMOPHENYL) 5 OXO 4,5 DIHYDROPYRANO[3,2 C]CHROMENE 3 CARBONITRILE; 2 AMINO 4 (4 FLUOROPHENYL) 4H BENZO[G]CHROMENE 3 CARBONITRILE; 2 AMINO 4 (4 FLUOROPHENYL) 7 HYDROXY 4H CHROMENE 3 CARBONITRILE; 2 AMINO 4 (4 OXO 4H CHROMEN 3 YL) 4H BENZO[G]CHROMENE 3 CARBONITRILE; 2 AMINO 5 OXO 4 (4 OXO 4H CHROMEN 3 YL) 4,5 DIHYDROPYRANO[3,2 C]CHROMENE 3 CARBONITRILE; 2 AMINO 7 HYDROXY 4 (1H INDOL 3 YL) 4H CHROMENE 3 CARBONITRILE; 2 AMINOCHROMENE 3 CARBONITRILE DERIVATIVE; 2 AMINOCHROMENENITRILE DERIVATIVE; 2' AMINO 7' HYDROXY 4 OXO 4H 4' [3,4' BICHROMENE] 3' CARBONITRILE; ALCOHOL DERIVATIVE; ANTILEUKEMIC AGENT; CASPASE 9; DIMETHYL SULFOXIDE; MALANONITRILE; NAVITOCLAX; NITRILE; PHENOL DERIVATIVE; PROTEIN BCL 2; UNCLASSIFIED DRUG; UNINDEXED DRUG; ANTINEOPLASTIC AGENT; BCL2 PROTEIN, HUMAN; BENZOPYRAN DERIVATIVE;

EID: 84907486209     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0107118     Document Type: Article
Times cited : (57)

References (32)
  • 1
    • 0034614637 scopus 로고    scopus 로고
    • The hallmarks of cancer
    • Hanahan D, Weinberg RA (2000) The hallmarks of cancer. Cell 100: 57-70.
    • (2000) Cell , vol.100 , pp. 57-70
    • Hanahan, D.1    Weinberg, R.A.2
  • 2
    • 33847328289 scopus 로고    scopus 로고
    • The Bcl-2 apoptotic switch in cancer development and therapy
    • Adams JM, Cory S (2007) The Bcl-2 apoptotic switch in cancer development and therapy. Oncogene 26: 1324-1337.
    • (2007) Oncogene , vol.26 , pp. 1324-1337
    • Adams, J.M.1    Cory, S.2
  • 3
    • 37549048249 scopus 로고    scopus 로고
    • The BCL-2 protein family: Opposing activities that mediate cell death
    • Youle RJ, Strasser A (2008) The BCL-2 protein family: opposing activities that mediate cell death. Nat Rev Mol Cell Biol 9: 47-59.
    • (2008) Nat Rev Mol Cell Biol , vol.9 , pp. 47-59
    • Youle, R.J.1    Strasser, A.2
  • 4
    • 0021821903 scopus 로고
    • Involvement of the bcl-2 gene in human follicular lymphoma
    • Tsujimoto Y, Cossman J, Jaffe E, Croce CM (1985) Involvement of the bcl-2 gene in human follicular lymphoma. Science 228: 1440-1443.
    • (1985) Science , vol.228 , pp. 1440-1443
    • Tsujimoto, Y.1    Cossman, J.2    Jaffe, E.3    Croce, C.M.4
  • 5
    • 0022971142 scopus 로고
    • Cloning and structural analysis of cDNAs for bcl-2 and a hybrid bcl-2/immunoglobulin transcript resulting from the t (14;18) translocation
    • Cleary ML, Smith SD, Sklar J (1986) Cloning and structural analysis of cDNAs for bcl-2 and a hybrid bcl-2/immunoglobulin transcript resulting from the t (14;18) translocation. Cell 47: 19-28.
    • (1986) Cell , vol.47 , pp. 19-28
    • Cleary, M.L.1    Smith, S.D.2    Sklar, J.3
  • 6
    • 0023786047 scopus 로고
    • Bcl-2 gene promotes haemopoietic cell survival and cooperates with c-myc to immortalize pre-B cells
    • Vaux DL, Cory S, Adams JM (1988) Bcl-2 gene promotes haemopoietic cell survival and cooperates with c-myc to immortalize pre-B cells. Nature 335: 440-442.
    • (1988) Nature , vol.335 , pp. 440-442
    • Vaux, D.L.1    Cory, S.2    Adams, J.M.3
  • 7
    • 56249144184 scopus 로고    scopus 로고
    • Discovery of an orally bioavailable small molecule inhibitor of prosurvival B-cell lymphoma 2 proteins
    • Park CM, Bruncko M, Adickes J, Bauch J, Ding H, et al. (2008) Discovery of an orally bioavailable small molecule inhibitor of prosurvival B-cell lymphoma 2 proteins. J Med Chem 51: 6902-6915.
    • (2008) J Med Chem , vol.51 , pp. 6902-6915
    • Park, C.M.1    Bruncko, M.2    Adickes, J.3    Bauch, J.4    Ding, H.5
  • 8
    • 84856603735 scopus 로고    scopus 로고
    • Bcl-xL-inhibitory BH3 mimetics (ABT- 737 or ABT-263) and the modulation of cytosolic calcium flux and platelet function
    • author reply 1321-1322
    • Schoenwaelder SM, Jackson SP (2012) Bcl-xL-inhibitory BH3 mimetics (ABT- 737 or ABT-263) and the modulation of cytosolic calcium flux and platelet function. Blood 119: 1320-1321; author reply 1321-1322.
    • (2012) Blood , vol.119 , pp. 1320-1321
    • Schoenwaelder, S.M.1    Jackson, S.P.2
  • 9
    • 84867341788 scopus 로고    scopus 로고
    • Structure-based discovery of BM-957 as a potent small-molecule inhibitor of Bcl-2 and Bcl-xL capable of achieving complete tumor regression
    • Chen J, Zhou H, Aguilar A, Liu L, Bai L, et al. (2012) Structure-based discovery of BM-957 as a potent small-molecule inhibitor of Bcl-2 and Bcl-xL capable of achieving complete tumor regression. J Med Chem 55: 8502-8514.
    • (2012) J Med Chem , vol.55 , pp. 8502-8514
    • Chen, J.1    Zhou, H.2    Aguilar, A.3    Liu, L.4    Bai, L.5
  • 10
    • 84873540049 scopus 로고    scopus 로고
    • ABT-199, a potent and selective BCL-2 inhibitor, achieves antitumor activity while sparing platelets
    • Souers AJ, Leverson JD, Boghaert ER, Ackler SL, Catron ND, et al. (2013) ABT-199, a potent and selective BCL-2 inhibitor, achieves antitumor activity while sparing platelets. Nat Med 19: 202-208.
    • (2013) Nat Med , vol.19 , pp. 202-208
    • Souers, A.J.1    Leverson, J.D.2    Boghaert, E.R.3    Ackler, S.L.4    Catron, N.D.5
  • 11
    • 34250904254 scopus 로고    scopus 로고
    • Discovery of 4- aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 3. Structure-activity relationships of fused rings at the 7,8-positions
    • Kemnitzer W, Drewe J, Jiang S, Zhang H, Zhao J, et al. (2007) Discovery of 4- aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 3. Structure-activity relationships of fused rings at the 7,8-positions. J Med Chem 50: 2858-2864.
    • (2007) J Med Chem , vol.50 , pp. 2858-2864
    • Kemnitzer, W.1    Drewe, J.2    Jiang, S.3    Zhang, H.4    Zhao, J.5
  • 12
    • 9444265410 scopus 로고    scopus 로고
    • Antivascular and antitumor evaluation of 2-amino-4-(3-bromo-4,5-dimethoxyphenyl)- 3-cyano-4H-chromenes, a novel series of anticancer agents
    • Gourdeau H, Leblond L, Hamelin B, Desputeau C, Dong K, et al. (2004) Antivascular and antitumor evaluation of 2-amino-4-(3-bromo-4,5-dimethoxyphenyl)- 3-cyano-4H-chromenes, a novel series of anticancer agents. Mol Cancer Ther 3: 1375-1384.
    • (2004) Mol Cancer Ther , vol.3 , pp. 1375-1384
    • Gourdeau, H.1    Leblond, L.2    Hamelin, B.3    Desputeau, C.4    Dong, K.5
  • 13
    • 12344252927 scopus 로고    scopus 로고
    • The small-molecule Bcl-2 inhibitor HA14-1 interacts synergistically with flavopiridol to induce mitochondrial injury and apoptosis in human myeloma cells through a free radical-dependent and Jun NH2-terminal kinase-dependent mechanism
    • Pei XY, Dai Y, Grant S (2004) The small-molecule Bcl-2 inhibitor HA14-1 interacts synergistically with flavopiridol to induce mitochondrial injury and apoptosis in human myeloma cells through a free radical-dependent and Jun NH2-terminal kinase-dependent mechanism. Mol Cancer Ther 3: 1513-1524.
    • (2004) Mol Cancer Ther , vol.3 , pp. 1513-1524
    • Pei, X.Y.1    Dai, Y.2    Grant, S.3
  • 14
    • 22744437978 scopus 로고    scopus 로고
    • Apoptosis-based therapies and drug targets
    • Fischer U, Schulze-Osthoff K (2005) Apoptosis-based therapies and drug targets. Cell Death Differ 12 Suppl 1: 942-961.
    • (2005) Cell Death Differ , vol.12 , pp. 942-961
    • Fischer, U.1    Schulze-Osthoff, K.2
  • 15
    • 33845940416 scopus 로고    scopus 로고
    • Structure-activity relationship studies of ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (HA 14-1), an antagonist for antiapoptotic Bcl-2 proteins to overcome drug resistance in cancer
    • Doshi JM, Tian D, Xing C (2006) Structure-activity relationship studies of ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (HA 14-1), an antagonist for antiapoptotic Bcl-2 proteins to overcome drug resistance in cancer. J Med Chem 49: 7731-7739.
    • (2006) J Med Chem , vol.49 , pp. 7731-7739
    • Doshi, J.M.1    Tian, D.2    Xing, C.3
  • 16
    • 1442286330 scopus 로고    scopus 로고
    • The role of Bcl-2 family members in tumorigenesis
    • Kirkin V, Joos S, Zornig M (2004) The role of Bcl-2 family members in tumorigenesis. Biochim Biophys Acta 1644: 229-249.
    • (2004) Biochim Biophys Acta , vol.1644 , pp. 229-249
    • Kirkin, V.1    Joos, S.2    Zornig, M.3
  • 17
    • 84904537925 scopus 로고    scopus 로고
    • Novel benzoxazine-based aglycones block glucose uptake in vivo by inhibiting glycosidases
    • Bharathkumar H, Sundaram MS, Jagadish S, Paricharak S, Hemshekhar M, et al. (2014) Novel benzoxazine-based aglycones block glucose uptake in vivo by inhibiting glycosidases. PLoS One 9: e102759.
    • (2014) PLoS One , vol.9 , pp. e102759
    • Bharathkumar, H.1    Sundaram, M.S.2    Jagadish, S.3    Paricharak, S.4    Hemshekhar, M.5
  • 18
    • 22544449600 scopus 로고    scopus 로고
    • New cholinesterase inhibitors: Synthesis and structure- activity relationship studies of 1, 2-benzisoxazole series and novel imidazolyl-d2- isoxazolines
    • Rangappa KS (2005) New cholinesterase inhibitors: synthesis and structure- activity relationship studies of 1, 2-benzisoxazole series and novel imidazolyl-d2- isoxazolines. Journal of physical organic chemistry 18: 773-778.
    • (2005) Journal of Physical Organic Chemistry , vol.18 , pp. 773-778
    • Rangappa, K.S.1
  • 19
    • 43049113156 scopus 로고    scopus 로고
    • Structural simplification of bioactive natural products with multicomponent synthesis. 2. Antiproliferative and antitubulin activities of pyrano[3,2-c]pyridones and pyrano[3,2-c]quinolones
    • Magedov IV, Manpadi M, Ogasawara MA, Dhawan AS, Rogelj S, et al. (2008) Structural simplification of bioactive natural products with multicomponent synthesis. 2. antiproliferative and antitubulin activities of pyrano[3,2-c]pyridones and pyrano[3,2-c]quinolones. J Med Chem 51: 2561-2570.
    • (2008) J Med Chem , vol.51 , pp. 2561-2570
    • Magedov, I.V.1    Manpadi, M.2    Ogasawara, M.A.3    Dhawan, A.S.4    Rogelj, S.5
  • 20
    • 0034721143 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of certain alpha, beta-unsaturated ketones and their corresponding fused pyridines as antiviral and cytotoxic agents
    • El-Subbagh HI, Abu-Zaid SM, Mahran MA, Badria FA, Al-Obaid AM (2000) Synthesis and biological evaluation of certain alpha, beta-unsaturated ketones and their corresponding fused pyridines as antiviral and cytotoxic agents. J Med Chem 43: 2915-2921.
    • (2000) J Med Chem , vol.43 , pp. 2915-2921
    • El-Subbagh, H.I.1    Abu-Zaid, S.M.2    Mahran, M.A.3    Badria, F.A.4    Al-Obaid, A.M.5
  • 21
    • 0141838893 scopus 로고    scopus 로고
    • Solution-phase synthesis of novel delta2-isoxazoline libraries via 1,3-dipolar cycloaddition and their antifungal properties
    • Basappa, Sadashiva MP, Mantelingu K, Swamy SN, Rangappa KS (2003) Solution-phase synthesis of novel delta2-isoxazoline libraries via 1,3-dipolar cycloaddition and their antifungal properties. Bioorg Med Chem 11: 4539-4544.
    • (2003) Bioorg Med Chem , vol.11 , pp. 4539-4544
    • Basappa1    Sadashiva, M.P.2    Mantelingu, K.3    Swamy, S.N.4    Rangappa, K.S.5
  • 22
    • 77956418569 scopus 로고    scopus 로고
    • A small oxazine compound as an anti-tumor agent: A novel pyranoside mimetic that binds to VEGF, HB-EGF, and TNF-alpha
    • Basappa, Murugan S, Kavitha CV, Purushothaman A, Nevin KG, et al. (2010) A small oxazine compound as an anti-tumor agent: a novel pyranoside mimetic that binds to VEGF, HB-EGF, and TNF-alpha. Cancer Lett 297: 231-243.
    • (2010) Cancer Lett , vol.297 , pp. 231-243
    • Basappa Murugan, S.1    Kavitha, C.V.2    Purushothaman, A.3    Nevin, K.G.4
  • 23
    • 84884537169 scopus 로고    scopus 로고
    • Chromenes: Potential new chemotherapeutic agents for cancer
    • Patil SA, Patil R, Pfeffer LM, Miller DD (2013) Chromenes: potential new chemotherapeutic agents for cancer. Future Med Chem 5: 1647-1660.
    • (2013) Future Med Chem , vol.5 , pp. 1647-1660
    • Patil, S.A.1    Patil, R.2    Pfeffer, L.M.3    Miller, D.D.4
  • 24
    • 33645059697 scopus 로고    scopus 로고
    • The small organic compound HA14-1 prevents Bcl-2 interaction with Bax to sensitize malignant glioma cells to induction of cell death
    • Manero F, Gautier F, Gallenne T, Cauquil N, Gree D, et al. (2006) The small organic compound HA14-1 prevents Bcl-2 interaction with Bax to sensitize malignant glioma cells to induction of cell death. Cancer Res 66: 2757-2764.
    • (2006) Cancer Res , vol.66 , pp. 2757-2764
    • Manero, F.1    Gautier, F.2    Gallenne, T.3    Cauquil, N.4    Gree, D.5
  • 25
    • 84875765575 scopus 로고    scopus 로고
    • P70S6 kinase is a target of the novel proteasome inhibitor 3,39-diamino-49-methoxyflavone during apoptosis in human myeloid tumor cells
    • Piedfer M, Bouchet S, Tang R, Billard C, Dauzonne D, et al. (2013) p70S6 kinase is a target of the novel proteasome inhibitor 3,39-diamino-49-methoxyflavone during apoptosis in human myeloid tumor cells. Biochim Biophys Acta 1833: 1316-1328.
    • (2013) Biochim Biophys Acta , vol.1833 , pp. 1316-1328
    • Piedfer, M.1    Bouchet, S.2    Tang, R.3    Billard, C.4    Dauzonne, D.5
  • 26
    • 0030614915 scopus 로고    scopus 로고
    • Structure of Bcl-xL-Bak peptide complex: Recognition between regulators of apoptosis
    • Sattler M, Liang H, Nettesheim D, Meadows RP, Harlan JE, et al. (1997) Structure of Bcl-xL-Bak peptide complex: recognition between regulators of apoptosis. Science 275: 983-986.
    • (1997) Science , vol.275 , pp. 983-986
    • Sattler, M.1    Liang, H.2    Nettesheim, D.3    Meadows, R.P.4    Harlan, J.E.5
  • 27
    • 34548047900 scopus 로고    scopus 로고
    • Crystal structure of ABT-737 complexed with Bcl-xL: Implications for selectivity of antagonists of the Bcl-2 family
    • Lee EF, Czabotar PE, Smith BJ, Deshayes K, Zobel K, et al. (2007) Crystal structure of ABT-737 complexed with Bcl-xL: implications for selectivity of antagonists of the Bcl-2 family. Cell Death Differ 14: 1711-1713.
    • (2007) Cell Death Differ , vol.14 , pp. 1711-1713
    • Lee, E.F.1    Czabotar, P.E.2    Smith, B.J.3    Deshayes, K.4    Zobel, K.5
  • 28
    • 77949693761 scopus 로고    scopus 로고
    • The FLT3 internal tandem duplication mutation is a secondary target of the aurora B kinase inhibitor AZD1152-HQPA in acute myelogenous leukemia cells
    • Grundy M, Seedhouse C, Shang S, Richardson J, Russell N, et al. (2010) The FLT3 internal tandem duplication mutation is a secondary target of the aurora B kinase inhibitor AZD1152-HQPA in acute myelogenous leukemia cells. Mol Cancer Ther 9: 661-672.
    • (2010) Mol Cancer Ther , vol.9 , pp. 661-672
    • Grundy, M.1    Seedhouse, C.2    Shang, S.3    Richardson, J.4    Russell, N.5
  • 29
    • 78349273297 scopus 로고    scopus 로고
    • Dual inhibition of PI3K and mTORC1/2 signaling by NVP-BEZ235 as a new therapeutic strategy for acute myeloid leukemia
    • Chapuis N, Tamburini J, Green AS, Vignon C, Bardet V, et al. (2010) Dual inhibition of PI3K and mTORC1/2 signaling by NVP-BEZ235 as a new therapeutic strategy for acute myeloid leukemia. Clin Cancer Res 16: 5424-5435.
    • (2010) Clin Cancer Res , vol.16 , pp. 5424-5435
    • Chapuis, N.1    Tamburini, J.2    Green, A.S.3    Vignon, C.4    Bardet, V.5
  • 31
    • 84903975823 scopus 로고    scopus 로고
    • Synthesis and characterization of novel 1,2-oxazine-based small molecules that targets acetylcholinesterase
    • Sukhorukov AY, Nirvanappa AC, Swamy J, Ioffe SL, Nanjunda Swamy S, et al. (2014) Synthesis and characterization of novel 1,2-oxazine-based small molecules that targets acetylcholinesterase. Bioorg Med Chem Lett 24: 3618-3621.
    • (2014) Bioorg Med Chem Lett , vol.24 , pp. 3618-3621
    • Sukhorukov, A.Y.1    Nirvanappa, A.C.2    Swamy, J.3    Ioffe, S.L.4    Nanjunda Swamy, S.5
  • 32
    • 84865051348 scopus 로고    scopus 로고
    • Anti-tumor activity of a novel HS-mimetic-vascular endothelial growth factor binding small molecule
    • Sugahara K, Thimmaiah KN, Bid HK, Houghton PJ, Rangappa KS (2012) Anti-tumor activity of a novel HS-mimetic-vascular endothelial growth factor binding small molecule. PLoS One 7: e39444.
    • (2012) PLoS One , vol.7 , pp. e39444
    • Sugahara, K.1    Thimmaiah, K.N.2    Bid, H.K.3    Houghton, P.J.4    Rangappa, K.S.5


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