메뉴 건너뛰기




Volumn 45, Issue 12, 2010, Pages 5781-5791

Synthesis and biological evaluation of 2-(3′,4′,5′- trimethoxybenzoyl)-3-aryl/arylaminobenzo[b]thiophene derivatives as a novel class of antiproliferative agents

Author keywords

Apoptosis; Benzo b thiophene; Microtubules

Indexed keywords

(3,4,5 TRIMETHOXYPHENYL) [3 (PHENYLAMINO)BENZO[B]THIOPHEN 2 YL]METHANONE; 2 (3',4',5' TRIMETHOXYBENZOYL) 3 (4' ETHOXYPHENYL)BENZO[B]THIOPHENE; [3 (4 CHLOROPHENYLAMINO)BENZO[B]THIOPHEN 2 YL] (3,4,5 TRIMETHOXYPHENYL)METHANONE; [3 (4 ETHOXYPHENYLAMINO) 6 METHYLBENZO[B]THIOPHEN 2 YL] (3,4,5 TRIMETHOXYPHENYL)METHANONE; [3 (4 ETHOXYPHENYLAMINO)BENZO[B]THIOPHEN 2 YL] (3,4,5 TRIMETHOXYPHENYL)METHANONE; [3 (4 METHOXYPHENYLAMINO)BENZO[B]THIOPHEN 2 YL] (3,4,5 TRIMETHOXYPHENYL)METHANONE; [3 (4 TOLYLAMINO) 6 METHYLBENZO[B]THIOPHEN 2 YL] (3,4,5 TRIMETHOXYPHENYL)METHANONE; [3 (4 TOLYLAMINO)BENZO[B]THIOPHEN 2 YL] (3,4,5 TRIMETHOXYPHENYL)METHANONE; ANTINEOPLASTIC AGENT; BENZOTHIOPHENE DERIVATIVE; CASPASE 3; CYCLIN B1; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; TUBULIN; UNCLASSIFIED DRUG;

EID: 78649333056     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.09.038     Document Type: Article
Times cited : (46)

References (46)
  • 1
    • 4344572092 scopus 로고    scopus 로고
    • Microtubule structure and its stabilisation
    • L.A. Amos Microtubule structure and its stabilisation Org. Biomol. Chem. 2 2004 2153 2160
    • (2004) Org. Biomol. Chem. , vol.2 , pp. 2153-2160
    • Amos, L.A.1
  • 2
    • 0033965785 scopus 로고    scopus 로고
    • Microtubule dynamics and tubulin interacting proteins
    • C.E. Walczak Microtubule dynamics and tubulin interacting proteins Curr. Opin. Cell. Biol. 12 2000 52 56
    • (2000) Curr. Opin. Cell. Biol. , vol.12 , pp. 52-56
    • Walczak, C.E.1
  • 3
    • 0032426329 scopus 로고    scopus 로고
    • Tubulin structure: Insights into microtubule properties and functions
    • K.H. Downing, and E. Nogales Tubulin structure: insights into microtubule properties and functions Curr. Opin. Struct. Biol. 8 1998 785 791
    • (1998) Curr. Opin. Struct. Biol. , vol.8 , pp. 785-791
    • Downing, K.H.1    Nogales, E.2
  • 4
    • 0034518173 scopus 로고    scopus 로고
    • Structural basis for the interaction of tubulin with proteins and drugs that affect microtubule dynamics
    • K.H. Downing Structural basis for the interaction of tubulin with proteins and drugs that affect microtubule dynamics Annu. Rev. Cell. Dev. Biol. 16 2000 89 111
    • (2000) Annu. Rev. Cell. Dev. Biol. , vol.16 , pp. 89-111
    • Downing, K.H.1
  • 6
    • 33646551448 scopus 로고    scopus 로고
    • Antitubulin agents for the treatment of cancer. A medicinal chemistry update
    • N. Mahindroo, J.P. Liou, J.Y. Chang, and H.P. Hsieh Antitubulin agents for the treatment of cancer. A medicinal chemistry update Exp. Opin. Ther. Pat. 16 2006 647 691
    • (2006) Exp. Opin. Ther. Pat. , vol.16 , pp. 647-691
    • Mahindroo, N.1    Liou, J.P.2    Chang, J.Y.3    Hsieh, H.P.4
  • 7
    • 1942438028 scopus 로고    scopus 로고
    • Microtubules as a target for anticancer drugs
    • M.A. Jordan, and L. Wilson Microtubules as a target for anticancer drugs Nat. Rev. Cancer 4 2004 253 265
    • (2004) Nat. Rev. Cancer , vol.4 , pp. 253-265
    • Jordan, M.A.1    Wilson, L.2
  • 9
    • 29344471072 scopus 로고    scopus 로고
    • Understanding microtubule dynamics for improved cancer therapy
    • S. Honore, E. Pasquier, and D. Braguer Understanding microtubule dynamics for improved cancer therapy Cell. Mol. Life Sci. 62 2005 3039 3065
    • (2005) Cell. Mol. Life Sci. , vol.62 , pp. 3039-3065
    • Honore, S.1    Pasquier, E.2    Braguer, D.3
  • 10
    • 20044379059 scopus 로고    scopus 로고
    • Review: Tubulin function, action of antitubulin drugs, and new drug development
    • F. Pellegrini, and D.R. Budman Review: tubulin function, action of antitubulin drugs, and new drug development Cancer Invest. 23 2005 264 273
    • (2005) Cancer Invest. , vol.23 , pp. 264-273
    • Pellegrini, F.1    Budman, D.R.2
  • 12
    • 0242386588 scopus 로고    scopus 로고
    • Natural semisynthetic and synthetic microtubule inhibitors for cancer therapy
    • T. Beckers, and S. Mahboobi Natural semisynthetic and synthetic microtubule inhibitors for cancer therapy Drugs Future 28 2003 767 785
    • (2003) Drugs Future , vol.28 , pp. 767-785
    • Beckers, T.1    Mahboobi, S.2
  • 14
    • 0024513175 scopus 로고
    • Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A-4
    • G.R. Pettit, S.B. Singh, E. Hamel, C.M. Lin, D.S. Alberts, and D. Garcia-Kendall Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A-4 Experentia 45 1989 209 211
    • (1989) Experentia , vol.45 , pp. 209-211
    • Pettit, G.R.1    Singh, S.B.2    Hamel, E.3    Lin, C.M.4    Alberts, D.S.5    Garcia-Kendall, D.6
  • 15
    • 0024427745 scopus 로고
    • Antimitotic natural products combretastatin A-4 and combretastatin A-2: Studies on the mechanism of their inhibition of the binding of colchicine to tubulin
    • C.M. Lin, H.H. Ho, G.R. Pettit, and E. Hamel Antimitotic natural products combretastatin A-4 and combretastatin A-2: studies on the mechanism of their inhibition of the binding of colchicine to tubulin Biochemistry 28 1989 6984 6991
    • (1989) Biochemistry , vol.28 , pp. 6984-6991
    • Lin, C.M.1    Ho, H.H.2    Pettit, G.R.3    Hamel, E.4
  • 16
    • 0041421003 scopus 로고    scopus 로고
    • Combretastatin A-4 analogues as antimitotic antitumor agents
    • N.H. Nam Combretastatin A-4 analogues as antimitotic antitumor agents Curr. Med. Chem. 10 2003 1697 1722
    • (2003) Curr. Med. Chem. , vol.10 , pp. 1697-1722
    • Nam, N.H.1
  • 20
    • 0035826341 scopus 로고    scopus 로고
    • A novel palladium-mediated coupling approach to 2,3-disubstituted benzo[b]thiophenes and its application to the synthesis of tubulin binding agents
    • B.L. Flynn, P. Verdier-Pinard, and E. Hamel A novel palladium-mediated coupling approach to 2,3-disubstituted benzo[b]thiophenes and its application to the synthesis of tubulin binding agents Org. Lett. 3 2001 651 654
    • (2001) Org. Lett. , vol.3 , pp. 651-654
    • Flynn, B.L.1    Verdier-Pinard, P.2    Hamel, E.3
  • 21
    • 0141518578 scopus 로고    scopus 로고
    • Structural requirements for the interaction of combretastatins with tubulin: How important is the trimethoxy unit?
    • K. Gaukroger, J.A. Hadfield, N.J. Lawrence, S. Nlan, and A.T. McGown Structural requirements for the interaction of combretastatins with tubulin: how important is the trimethoxy unit? Org. Biomol. Chem. 1 2003 3033 3037
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 3033-3037
    • Gaukroger, K.1    Hadfield, J.A.2    Lawrence, N.J.3    Nlan, S.4    McGown, A.T.5
  • 23
    • 37049141616 scopus 로고
    • 1,2-Benzisothiazoles. Part I. Reaction of 3-chloro-1,2-benzisothiazole with nucleophiles
    • D.E.L. Carrington, K. Clarke, and R.M. Scrowston 1,2-Benzisothiazoles. Part I. Reaction of 3-chloro-1,2-benzisothiazole with nucleophiles J. Chem. Soc. 1971 3262 3265
    • (1971) J. Chem. Soc. , pp. 3262-3265
    • Carrington, D.E.L.1    Clarke, K.2    Scrowston, R.M.3
  • 24
    • 84987333000 scopus 로고
    • A facile synthesis of 2-phenylbenzo[b]thiophene-3-amine and the corresponding S-oxide
    • J.R. Beck A facile synthesis of 2-phenylbenzo[b]thiophene-3-amine and the corresponding S-oxide J. Heterocycl. Chem. 15 1978 513 514
    • (1978) J. Heterocycl. Chem. , vol.15 , pp. 513-514
    • Beck, J.R.1
  • 25
    • 0000249892 scopus 로고
    • Alkyl nitrite-metal halide deamination reactions. 2. Substitutive deamination of arylamines by alkyl nitrites and copper (II) halides. A direct and remarkably efficient conversion of arylamines to aryl halides
    • M.P. Doyle, B. Siegfried, and J.F. Dellaria Jr. Alkyl nitrite-metal halide deamination reactions. 2. Substitutive deamination of arylamines by alkyl nitrites and copper (II) halides. A direct and remarkably efficient conversion of arylamines to aryl halides J. Org. Chem. 42 1977 2426 2431
    • (1977) J. Org. Chem. , vol.42 , pp. 2426-2431
    • Doyle, M.P.1    Siegfried, B.2    Dellaria Jr., J.F.3
  • 26
    • 33751391090 scopus 로고
    • A simple asymmetric synthesis of 4-arylphenylalanines via palladium-catalyzed cross-coupling reaction of arylboronic acids with tyrosine triflate
    • W.C. Shieh, and J.A. Carlson A simple asymmetric synthesis of 4-arylphenylalanines via palladium-catalyzed cross-coupling reaction of arylboronic acids with tyrosine triflate J. Org. Chem. 57 1992 379 381
    • (1992) J. Org. Chem. , vol.57 , pp. 379-381
    • Shieh, W.C.1    Carlson, J.A.2
  • 27
    • 4544374058 scopus 로고    scopus 로고
    • Palladium-catalysed amination of electron-deficient or relatively electron-rich benzo[b]thienyl bromides-preliminary studies of antimicrobial activity and SARs
    • M.-J.R. Queiroz, A. Begouin, I.C.F.R. Ferreira, G. Kirsch, R.C. Calhelha, S. Barbosa, and L.M. Estevinho Palladium-catalysed amination of electron-deficient or relatively electron-rich benzo[b]thienyl bromides-preliminary studies of antimicrobial activity and SARs Eur. J. Org. Chem. 2004 3679 3685
    • (2004) Eur. J. Org. Chem. , pp. 3679-3685
    • Queiroz, M.-J.R.1    Begouin, A.2    Ferreira, I.C.F.R.3    Kirsch, G.4    Calhelha, R.C.5    Barbosa, S.6    Estevinho, L.M.7
  • 28
    • 0037419179 scopus 로고    scopus 로고
    • Scope and mechanism of palladium-catalyzed amination of five-membered heterocyclic halides
    • M.W. Hooper, M. Utsunomiya, and J.F. Hartwig Scope and mechanism of palladium-catalyzed amination of five-membered heterocyclic halides J. Org. Chem. 68 2003 2861 2873
    • (2003) J. Org. Chem. , vol.68 , pp. 2861-2873
    • Hooper, M.W.1    Utsunomiya, M.2    Hartwig, J.F.3
  • 29
    • 0142036683 scopus 로고    scopus 로고
    • Evaluation of antimitotic agents by quantitative comparisons of their effects on the polymerization of purified tubulin
    • E. Hamel Evaluation of antimitotic agents by quantitative comparisons of their effects on the polymerization of purified tubulin Cell Biochem. Biophys. 38 2003 1 21
    • (2003) Cell Biochem. Biophys. , vol.38 , pp. 1-21
    • Hamel, E.1
  • 30
    • 0141996464 scopus 로고    scopus 로고
    • Microtubules, microtubule-interfering agents and apoptosis
    • F. Mollinedo, and C. Gajate Microtubules, microtubule-interfering agents and apoptosis Apoptosis 8 2003 413 450
    • (2003) Apoptosis , vol.8 , pp. 413-450
    • Mollinedo, F.1    Gajate, C.2
  • 31
    • 61749102378 scopus 로고    scopus 로고
    • Cell-cycle control in the face of damage - A matter of life or death
    • P.R. Clarke, and L.A. Allan Cell-cycle control in the face of damage - a matter of life or death Trends Cell Biol. 19 2009 89 98
    • (2009) Trends Cell Biol. , vol.19 , pp. 89-98
    • Clarke, P.R.1    Allan, L.A.2
  • 32
    • 0028800947 scopus 로고
    • Early redistribution of plasma membrane phosphatidylserine is a general feature of apoptosis regardless of the initiating stimulus: Inhibition by overexpression of Bcl-2 and Abl
    • S.J. Martin, C.P. Reutelingsperger, A.J. McGahon, J.A. Rader, R.C. van Schie, D.M. Laface, and D.R. Green Early redistribution of plasma membrane phosphatidylserine is a general feature of apoptosis regardless of the initiating stimulus: inhibition by overexpression of Bcl-2 and Abl J. Exp. Med. 182 1995 1545 1556
    • (1995) J. Exp. Med. , vol.182 , pp. 1545-1556
    • Martin, S.J.1    Reutelingsperger, C.P.2    McGahon, A.J.3    Rader, J.A.4    Van Schie, R.C.5    Laface, D.M.6    Green, D.R.7
  • 33
    • 0029043888 scopus 로고
    • A novel assay for apoptosis. Flow cytometric detection of phosphatidylserine expression on early apoptotic cells using fluorescein labelled annexin v
    • I. Vermes, C. Haanen, H. Steffens-Nakken, and C. Reutelingsperger A novel assay for apoptosis. Flow cytometric detection of phosphatidylserine expression on early apoptotic cells using fluorescein labelled annexin V J. Immunol. Methods 184 1995 39 51
    • (1995) J. Immunol. Methods , vol.184 , pp. 39-51
    • Vermes, I.1    Haanen, C.2    Steffens-Nakken, H.3    Reutelingsperger, C.4
  • 34
    • 3442886811 scopus 로고    scopus 로고
    • The pathophysiology of mitochondrial cell death
    • D.R. Green, and G. Kroemer The pathophysiology of mitochondrial cell death Science 305 2005 626 629
    • (2005) Science , vol.305 , pp. 626-629
    • Green, D.R.1    Kroemer, G.2
  • 35
    • 0037879052 scopus 로고    scopus 로고
    • The mitochondrial membrane potential (Δψm) in apoptosis: An update
    • J.D. Ly, D.R. Grubb, and A. Lawen The mitochondrial membrane potential (Δψm) in apoptosis: an update Apoptosis 3 2003 115 128
    • (2003) Apoptosis , vol.3 , pp. 115-128
    • Ly, J.D.1    Grubb, D.R.2    Lawen, A.3
  • 36
    • 0142042958 scopus 로고    scopus 로고
    • Rhodamine 123 as a probe of mitochondrial membrane potential: Evaluation of proton flux through F0 during ATP synthesis
    • A. Baracca, G. Sgarbi, G. Solaini, and G. Lenaz Rhodamine 123 as a probe of mitochondrial membrane potential: evaluation of proton flux through F0 during ATP synthesis Biochim. Biophys. Acta Bioenerg. 1606 2003 137 145
    • (2003) Biochim. Biophys. Acta Bioenerg. , vol.1606 , pp. 137-145
    • Baracca, A.1    Sgarbi, G.2    Solaini, G.3    Lenaz, G.4
  • 38
    • 13844262622 scopus 로고    scopus 로고
    • Intracellular generation of reactive oxygen species by mitochondria
    • H. Nohl, L. Gille, and K. Staniek Intracellular generation of reactive oxygen species by mitochondria Biochem. Pharmacol. 69 2005 719 723
    • (2005) Biochem. Pharmacol. , vol.69 , pp. 719-723
    • Nohl, H.1    Gille, L.2    Staniek, K.3
  • 39
    • 0025218905 scopus 로고
    • Flow cytometric analysis of respiratory burst activity in phagocytes with hydroethidine and 2′,7′-dichlorofluorescein
    • G. Rothe, and G. Valet Flow cytometric analysis of respiratory burst activity in phagocytes with hydroethidine and 2′,7′- dichlorofluorescein J. Leukoc. Biol. 47 1990 440 448
    • (1990) J. Leukoc. Biol. , vol.47 , pp. 440-448
    • Rothe, G.1    Valet, G.2
  • 40
    • 0032885388 scopus 로고    scopus 로고
    • Mammalian caspases: Structure, activation, substrates and functions during apoptosis
    • W.C. Earshaw, L.M. Martins, and S.H. Kaufmann Mammalian caspases: structure, activation, substrates and functions during apoptosis Annu. Rev. Biochem. 68 1999 383 424
    • (1999) Annu. Rev. Biochem. , vol.68 , pp. 383-424
    • Earshaw, W.C.1    Martins, L.M.2    Kaufmann, S.H.3
  • 41
    • 0036931366 scopus 로고    scopus 로고
    • Caspases: Keys in the ignition of cell death
    • J.-B. Denault, and G.S. Salvesen Caspases: keys in the ignition of cell death Chem. Rev. 102 2002 4489 4499
    • (2002) Chem. Rev. , vol.102 , pp. 4489-4499
    • Denault, J.-B.1    Salvesen, G.S.2
  • 42
    • 0344142396 scopus 로고    scopus 로고
    • Emerging role of caspase-3 in apoptosis
    • A.G. Porter, and R.U. Janicke Emerging role of caspase-3 in apoptosis Cell Death Differ. 6 1999 99 104
    • (1999) Cell Death Differ. , vol.6 , pp. 99-104
    • Porter, A.G.1    Janicke, R.U.2
  • 43
    • 0036022402 scopus 로고    scopus 로고
    • Poly(ADP-ribose) polymerase-1 cleavage during apoptosis: An update
    • C. Soldani, and A.I. Scovassi Poly(ADP-ribose) polymerase-1 cleavage during apoptosis: an update Apoptosis 7 2002 321 328
    • (2002) Apoptosis , vol.7 , pp. 321-328
    • Soldani, C.1    Scovassi, A.I.2
  • 44
    • 0031037897 scopus 로고    scopus 로고
    • The release of cytochrome c from mitochondria: A primary site for Bcl-2 regulation of apoptosis
    • R.M. Kluck, E. Bossy-Wetzel, and D.R. Green The release of cytochrome c from mitochondria: a primary site for Bcl-2 regulation of apoptosis Science 275 1997 1132 1136
    • (1997) Science , vol.275 , pp. 1132-1136
    • Kluck, R.M.1    Bossy-Wetzel, E.2    Green, D.R.3
  • 45
    • 0030861571 scopus 로고    scopus 로고
    • Bcl-2 and Bax function independently to regulate cell death
    • C.M. Knudson, and S.J. Korsmeyer Bcl-2 and Bax function independently to regulate cell death Nat. Genet. 16 1997 358 363
    • (1997) Nat. Genet. , vol.16 , pp. 358-363
    • Knudson, C.M.1    Korsmeyer, S.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.