메뉴 건너뛰기




Volumn 65, Issue , 2013, Pages 21-31

Synthesis and structure-activity relationships of N2-alkylated quaternary β-carbolines as novel antitumor agents

Author keywords

Antitumor; Cytotoxic; Structure activity relationships; Synthesis; Carboline

Indexed keywords

1 (4 METHOXYPHENYL) BETA CARBOLINE; 1 (METHOXYPHENYL) 9 (3 PHENYLPROPYL)BETA CARBOLINE; 1 (THIOPEN 3 YL) BETA CARBOLINE; 1 METHYL 9 (3 PHENYLPROPYL)BETA CARBOLINE; 1 PHENYL 9 (3 PHENYLPROPYL)BETA CARBOLINE; 1 PHENYL BETA CARBOLINE; 2 BENZYL 9 ALLYL BETA CARBOLINIUM BROMIDE; 2 BENZYL 9 BUTYL BETA CARBOLINIUM BROMIDE; 2 BENZYL 9 ETHYL BETA CARBOLINIUM BROMIDE; 2 BENZYL 9 HEXYL BETA CARBOLINIUM BROMIDE; 2 BENZYL 9 ISOBUTYL BETA CARBOLINIUM BROMIDE; 2 BENZYL 9 ISOPROPYL BETA CARBOLINIUM BROMIDE; 2 BENZYL 9 METHYL BETA CARBOLINIUM BROMIDE; 2 BENZYL 9 OCTYL BETA CARBOLINIUM BROMIDE; 9 (3 CHLOROBENZYL)L BETA CARBOLINE; 9 (3 PHENYLPROPYL) 1 (THIOPEN 3 YL) BETA CARBOLINE; 9 (3 PHENYPROPYL) BETA CARBOLINE; 9 (4 CHLOROBENZYL) 2 BENZYL BETA CARBOLINIUM BROMIDE; 9 (4 FLUOROBENZYL) 2 BENZYL BETA CARBOLINIUM BROMIDE; 9 (4 FLUOROBENZYL)L BETA CARBOLINE; 9 (4 METHOXYBENZYL) 2 BENZYL BETA CARBOLINIUM BROMIDE; 9 (4 METHOXYBENZYL) BETA CARBOLINE; 9 ALLYL BETA CARBOLINE; 9 HEXYL BETA CARBOLINE; 9 ISOBUTYL BETA CARBOLINE; 9 ISOPROPYL BETA CARBOLINE; 9 OCTYL BETA CARBOLINE; ANTINEOPLASTIC AGENT; BETA CARBOLINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 84884271207     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.04.031     Document Type: Article
Times cited : (51)

References (41)
  • 1
    • 33847241204 scopus 로고    scopus 로고
    • β-Carboline alkaloids: Biochemical and pharmacological functions
    • R. Cao, W. Peng, Z. Wang, A. Xu, β-Carboline alkaloids: biochemical and pharmacological functions, Curr. Med. Chem. 14 (2007) 479-500.
    • (2007) Curr. Med. Chem. , vol.14 , pp. 479-500
    • Cao, R.1    Peng, W.2    Wang, Z.3    Xu, A.4
  • 3
    • 0035952254 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of DNA targeting flexible side-chain substituted β-carboline derivatives
    • S. Xiao, W. Lin, C. Wang, M. Yang, Synthesis and biological evaluation of DNA targeting flexible side-chain substituted β-carboline derivatives, Bioorg. Med. Chem. Lett. 11 (2001) 437-441.
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 437-441
    • Xiao, S.1    Lin, W.2    Wang, C.3    Yang, M.4
  • 5
    • 33748124815 scopus 로고    scopus 로고
    • Synthesis and cytotoxic activities of β-carboline amino acid ester conjugates
    • M. Zhao, L. Bi, W. Wang, C. Wang, M. Baudy-Floch, J. Ju, S. Peng, Synthesis and cytotoxic activities of β-carboline amino acid ester conjugates, Bioorg. Med. Chem. 18 (2006) 6998-7010.
    • (2006) Bioorg. Med. Chem. , vol.18 , pp. 6998-7010
    • Zhao, M.1    Bi, L.2    Wang, W.3    Wang, C.4    Baudy-Floch, M.5    Ju, J.6    Peng, S.7
  • 7
    • 67651151054 scopus 로고    scopus 로고
    • Novel N-(3-carboxyl-9-benzyl-β-carboline-1-yl)ethylamino acids: Synthesis, anti-tumor evaluation, intercalating determination, 3D QSAR analysis and docking investigation
    • J. Wu, M. Zhao, K. Qian, K.-H. Lee, S. Morris-Natschke, S. Peng, Novel N-(3-carboxyl-9-benzyl-β-carboline-1-yl)ethylamino acids: synthesis, anti-tumor evaluation, intercalating determination, 3D QSAR analysis and docking investigation, Eur. J. Med. Chem. 44 (2009) 4153-4161.
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 4153-4161
    • Wu, J.1    Zhao, M.2    Qian, K.3    Lee, K.-H.4    Morris-Natschke, S.5    Peng, S.6
  • 9
    • 79952191668 scopus 로고    scopus 로고
    • Synthesis, in vitro anti-inflammatory and cytotoxic evaluation, and mechanism of action studies of 1-benzoyl-β-carboline and 1-benzoyl-3- carboxy-β-carboline derivatives
    • M. Yang, P.-C. Kuo, T.-L. Hwang, W.-F. Chiou, K. Qian, C.-Y. Lai, K.-H. Lee, T.-S. Wu, Synthesis, in vitro anti-inflammatory and cytotoxic evaluation, and mechanism of action studies of 1-benzoyl-β-carboline and 1-benzoyl-3- carboxy-β-carboline derivatives, Bioorg. Med. Chem. 19 (2011) 1674-1682.
    • (2011) Bioorg. Med. Chem. , vol.19 , pp. 1674-1682
    • Yang, M.1    Kuo, P.-C.2    Hwang, T.-L.3    Chiou, W.-F.4    Qian, K.5    Lai, C.-Y.6    Lee, K.-H.7    Wu, T.-S.8
  • 10
    • 0019450012 scopus 로고
    • Linear and circular dichroism of harmine and harmaline interacting with DNA
    • G. Duportail, Linear and circular dichroism of harmine and harmaline interacting with DNA, Int. J. Biol. Macromol. 3 (1981) 188-193.
    • (1981) Int. J. Biol. Macromol. , vol.3 , pp. 188-193
    • Duportail, G.1
  • 13
    • 0036234519 scopus 로고    scopus 로고
    • An in vitro evaluation of human DNA topoisomerase I inhibition by Peganum harmala L. Seeds extract and its β-carboline alkaloids
    • A.M. Sobhani, S.A. Ebrahimi, M. Mahmoudian, An in vitro evaluation of human DNA topoisomerase I inhibition by Peganum harmala L. seeds extract and its β-carboline alkaloids, J. Pharm. Pharm. Sci. 5 (2002) 19-23.
    • (2002) J. Pharm. Pharm. Sci. , vol.5 , pp. 19-23
    • Sobhani, A.M.1    Ebrahimi, S.A.2    Mahmoudian, M.3
  • 20
    • 4043114875 scopus 로고    scopus 로고
    • Synthesis, acute toxicities and antitumor effects of novel 9-substituted β-carboline derivatives
    • R. Cao, Q. Chen, X. Hou, H. Chen, H. Guan, Y. Ma, W. Peng, A. Xu, Synthesis, acute toxicities and antitumor effects of novel 9-substituted β-carboline derivatives, Bioorg. Med. Chem. 12 (2004) 4613-4623.
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 4613-4623
    • Cao, R.1    Chen, Q.2    Hou, X.3    Chen, H.4    Guan, H.5    Ma, Y.6    Peng, W.7    Xu, A.8
  • 21
    • 13844255204 scopus 로고    scopus 로고
    • Synthesis and in vitro cytotoxic evaluation of 1,3-bisubstituted and 1,3,9-trisubstituted β-carboline derivatives
    • R. Cao, W. Peng, H. Chen, X. Hou, H. Guan, Q. Chen, Y. Ma, A. Xu, Synthesis and in vitro cytotoxic evaluation of 1,3-bisubstituted and 1,3,9-trisubstituted β-carboline derivatives, Eur. J. Med. Chem. 40 (2005) 249-257.
    • (2005) Eur. J. Med. Chem. , vol.40 , pp. 249-257
    • Cao, R.1    Peng, W.2    Chen, H.3    Hou, X.4    Guan, H.5    Chen, Q.6    Ma, Y.7    Xu, A.8
  • 22
    • 26444497133 scopus 로고    scopus 로고
    • Design, synthesis and in vitro and in vivo antitumor activities of novel β-carboline derivatives
    • R. Cao, H. Chen, W. Peng, Y. Ma, X. Hou, H. Guan, X. Liu, A. Xu, Design, synthesis and in vitro and in vivo antitumor activities of novel β-carboline derivatives, Eur. J. Med. Chem. 40 (2005) 991-1001.
    • (2005) Eur. J. Med. Chem. , vol.40 , pp. 991-1001
    • Cao, R.1    Chen, H.2    Peng, W.3    Ma, Y.4    Hou, X.5    Guan, H.6    Liu, X.7    Xu, A.8
  • 23
    • 33750012817 scopus 로고    scopus 로고
    • Design of β-carboline derivatives as DNA-targeting antitumor agents
    • H. Guan, H. Chen, W. Peng, Y. Ma, R. Cao, X. Liu, A. Xu, Design of β-carboline derivatives as DNA-targeting antitumor agents, Eur. J. Med. Chem. 41 (2006) 1167-1179.
    • (2006) Eur. J. Med. Chem. , vol.41 , pp. 1167-1179
    • Guan, H.1    Chen, H.2    Peng, W.3    Ma, Y.4    Cao, R.5    Liu, X.6    Xu, A.7
  • 24
  • 25
    • 60149096806 scopus 로고    scopus 로고
    • Synthesis and in vitro cytotoxic evaluation of novel 3,4,5- trimethoxyphenyl substituted β-carboline derivatives
    • Q. Wu, R. Cao, M. Feng, X. Guan, C. Ma, J. Liu, H. Song, W. Peng, Synthesis and in vitro cytotoxic evaluation of novel 3,4,5-trimethoxyphenyl substituted β-carboline derivatives, Eur. J. Med. Chem. 44 (2009) 533-540.
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 533-540
    • Wu, Q.1    Cao, R.2    Feng, M.3    Guan, X.4    Ma, C.5    Liu, J.6    Song, H.7    Peng, W.8
  • 27
    • 77950862722 scopus 로고    scopus 로고
    • Design, synthesis and 3D-QSAR of β-carboline derivatives as potent antitumor agents
    • R. Cao, X. Guan, B. Shi, Z. Chen, Z. Ren, W. Peng, H. Song, Design, synthesis and 3D-QSAR of β-carboline derivatives as potent antitumor agents, Eur. J. Med. Chem. 45 (2010) 2503-2515.
    • (2010) Eur. J. Med. Chem. , vol.45 , pp. 2503-2515
    • Cao, R.1    Guan, X.2    Shi, B.3    Chen, Z.4    Ren, Z.5    Peng, W.6    Song, H.7
  • 28
    • 77954313859 scopus 로고    scopus 로고
    • Synthesis of novel β-carbolines with efficient DNA-binding capacity and potent cytotoxicity
    • Z. Chen, R. Cao, B. Shi, Y. Wei, L. Yu, H. Song, Z. Ren, W. Peng, Synthesis of novel β-carbolines with efficient DNA-binding capacity and potent cytotoxicity, Bioorg. Med. Chem. Lett. 20 (2010) 3876-3879.
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 3876-3879
    • Chen, Z.1    Cao, R.2    Shi, B.3    Wei, Y.4    Yu, L.5    Song, H.6    Ren, Z.7    Peng, W.8
  • 30
    • 77957835162 scopus 로고    scopus 로고
    • Synthesis and cytotoxic evaluation of 1-carboxamide and 1-amino side chain substituted β-carbolines
    • C. Ma, R. Cao, B. Shi, X. Zhou, Q. Ma, J. Sun, L. Guo, W. Yi, Z. Chen, H. Song, Synthesis and cytotoxic evaluation of 1-carboxamide and 1-amino side chain substituted β-carbolines, Eur. J. Med. Chem. 45 (2010) 5513-5519.
    • (2010) Eur. J. Med. Chem. , vol.45 , pp. 5513-5519
    • Ma, C.1    Cao, R.2    Shi, B.3    Zhou, X.4    Ma, Q.5    Sun, J.6    Guo, L.7    Yi, W.8    Chen, Z.9    Song, H.10
  • 31
    • 80053185089 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of 1,9-disubstituted β-carbolines as potent DNA intercalating and cytotoxic agents
    • Z. Chen, R. Cao, B. Shi, L. Guo, J. Sun, Q. Ma, W. Fan, H. Song, Synthesis and biological evaluation of 1,9-disubstituted β-carbolines as potent DNA intercalating and cytotoxic agents, Eur. J. Med. Chem. 46 (2011) 5127-5137.
    • (2011) Eur. J. Med. Chem. , vol.46 , pp. 5127-5137
    • Chen, Z.1    Cao, R.2    Shi, B.3    Guo, L.4    Sun, J.5    Ma, Q.6    Fan, W.7    Song, H.8
  • 32
    • 84871716160 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationships of harmine derivatives as potential antitumor agents
    • R. Cao, W. Fan, L. Guo, Q. Ma, G. Zhang, J. Li, X. Chen, Z. Ren, L. Qiu, Synthesis and structure-activity relationships of harmine derivatives as potential antitumor agents, Eur. J. Med. Chem. 60 (2013) 135-143.
    • (2013) Eur. J. Med. Chem. , vol.60 , pp. 135-143
    • Cao, R.1    Fan, W.2    Guo, L.3    Ma, Q.4    Zhang, G.5    Li, J.6    Chen, X.7    Ren, Z.8    Qiu, L.9
  • 34
    • 0030462914 scopus 로고    scopus 로고
    • Antibody microinjection reveals an essential role for human polo-like kinase 1 (Plk1) in the functional maturation of mitotic centrosomes
    • H.A. Lane, E.A. Nigg, Antibody microinjection reveals an essential role for human polo-like kinase 1 (Plk1) in the functional maturation of mitotic centrosomes, J. Cell. Biol. 135 (1996) 1701-1713.
    • (1996) J. Cell. Biol. , vol.135 , pp. 1701-1713
    • Lane, H.A.1    Nigg, E.A.2
  • 35
    • 4344718620 scopus 로고    scopus 로고
    • Polo-like kinase-1 is required for bipolar spindle formation but is dispensable for anaphase promoting complex/Cdc20 activation and initiation of cytokinesis
    • M.A. van Vugt, Weerdt B.C. van de, G. Vader, H. Janssen, J. Calafat, R. Klompmaker, R.M. Wolthuis, R.H. Medema, Polo-like kinase-1 is required for bipolar spindle formation but is dispensable for anaphase promoting complex/Cdc20 activation and initiation of cytokinesis, J. Biol. Chem. 279 (2004) 36841-36854.
    • (2004) J. Biol. Chem. , vol.279 , pp. 36841-36854
    • Van Vugt, M.A.1    Van De Weerdt, B.C.2    Vader, G.3    Janssen, H.4    Calafat, J.5    Klompmaker, R.6    Wolthuis, R.M.7    Medema, R.H.8
  • 37
    • 0038624074 scopus 로고    scopus 로고
    • Polo-like kinase (Plk) 1 depletion induces apoptosis in cancer cells
    • X. Liu, R.L. Erikson, Polo-like kinase (Plk) 1 depletion induces apoptosis in cancer cells, Proc. Natl. Acad. Sci. U. S. A. 100 (2003) 5789-5794.
    • (2003) Proc. Natl. Acad. Sci. U. S. A. , vol.100 , pp. 5789-5794
    • Liu, X.1    Erikson, R.L.2
  • 38
    • 16844369144 scopus 로고    scopus 로고
    • Small interfering RNA-mediated polo-like kinase 1 depletion preferentially reduces the survival of p53-defective, oncogenic transformed cells and inhibits tumor growth in animals
    • R. Guan, P. Tapang, J.D. Leverson, D. Albert, V.L. Giranda, Y. Luo, Small interfering RNA-mediated polo-like kinase 1 depletion preferentially reduces the survival of p53-defective, oncogenic transformed cells and inhibits tumor growth in animals, Cancer Res. 65 (2005) 2698-2704.
    • (2005) Cancer Res. , vol.65 , pp. 2698-2704
    • Guan, R.1    Tapang, P.2    Leverson, J.D.3    Albert, D.4    Giranda, V.L.5    Luo, Y.6
  • 41
    • 0037102721 scopus 로고    scopus 로고
    • A comparison of the efficacy of pyridostigmine alone and the combination of pyridostigmine with anticholinergic drugs as pharmacological pretreatment of tabun-poisoned rats and mice
    • J. Kassa, J. Vachek, A comparison of the efficacy of pyridostigmine alone and the combination of pyridostigmine with anticholinergic drugs as pharmacological pretreatment of tabun-poisoned rats and mice, Toxicology 177 (2002) 179-185.
    • (2002) Toxicology , vol.177 , pp. 179-185
    • Kassa, J.1    Vachek, J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.