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Volumn 38, Issue 24, 2008, Pages 4415-4425

Synthesis and characterization of 8-(2-((trimethylsilyl)ethynyl) phenylamino)-7H-naphtho[1,8-bc]acridin-7-one

Author keywords

2 (trimethylsilylethynyl)aniline; Acenaphthenequinone; Acridine; Cyclization; Heterocycle

Indexed keywords

8(2((TRIMETHYSILYL)ETHYNYL)PHENYLAMINO)7H NAPHTHO[1,8BC]ACRIDIN 7 ONE; ACRIDINE; ACRIDINE DERIVATIVE; AROMATIC COMPOUND; HETEROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

EID: 57349162194     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802369539     Document Type: Article
Times cited : (5)

References (34)
  • 1
    • 11144339340 scopus 로고    scopus 로고
    • Biological activities of pyridoacridines
    • (a) Marshall, K. M.; Barrows, L. R. Biological activities of pyridoacridines. Nat. Prod. Rep. 2004, 21, 731;
    • (2004) Nat. Prod. Rep , vol.21 , pp. 731
    • Marshall, K.M.1    Barrows, L.R.2
  • 2
    • 0037369126 scopus 로고    scopus 로고
    • Marine pyridoacridine alkaloids and synthetic analogues as antitumor agents
    • (b) Delfourne, E.; Bastide, J. Marine pyridoacridine alkaloids and synthetic analogues as antitumor agents. Med. Res. Rev. 2003, 23, 234;
    • (2003) Med. Res. Rev , vol.23 , pp. 234
    • Delfourne, E.1    Bastide, J.2
  • 4
    • 0032956510 scopus 로고    scopus 로고
    • Pyrroloquinoline and pyridoacridine alkaloids from marine sources
    • (d) Ding, Q.; Chichak, K.; Lown, J. W. Pyrroloquinoline and pyridoacridine alkaloids from marine sources. Curr. Med. Chem. 1999, 6, 1;
    • (1999) Curr. Med. Chem , vol.6 , pp. 1
    • Ding, Q.1    Chichak, K.2    Lown, J.W.3
  • 5
    • 0000331562 scopus 로고
    • Marine pyridoacridine alkaloids: Structure, synthesis, and biological chemistry
    • (e) Molinski, T. F. Marine pyridoacridine alkaloids: Structure, synthesis, and biological chemistry. Chem. Rev. 1993, 93, 1825;
    • (1993) Chem. Rev , vol.93 , pp. 1825
    • Molinski, T.F.1
  • 6
    • 0025768698 scopus 로고
    • The genetic toxicology of acridines
    • (f) Ferguson, L. R.; Denny, W. A. The genetic toxicology of acridines. Mutat. Res. 1991, 258, 123.
    • (1991) Mutat. Res , vol.258 , pp. 123
    • Ferguson, L.R.1    Denny, W.A.2
  • 7
    • 0035177432 scopus 로고    scopus 로고
    • Acridine - A neglected antibacterial chromophore
    • (a) Wainwright, M. Acridine - A neglected antibacterial chromophore. J. Antimicrob. Chemother. 2001, 47, 1;
    • (2001) J. Antimicrob. Chemother , vol.47 , pp. 1
    • Wainwright, M.1
  • 8
    • 0034781209 scopus 로고    scopus 로고
    • Interest of acridine derivatives in the anticancer chemotherapy
    • (b) Demeunynck, M.; Charmantray, F.; Martelli, A. Interest of acridine derivatives in the anticancer chemotherapy. Curr. Pharm. Des. 2001, 7, 1703;
    • (2001) Curr. Pharm. Des , vol.7 , pp. 1703
    • Demeunynck, M.1    Charmantray, F.2    Martelli, A.3
  • 9
    • 0035959980 scopus 로고    scopus 로고
    • Antonini, I.; Polucci, P.; Magnano, A.; Sante, M. Synthesis, antitumor cytotoxicity, and DNA-binding of novel N-5,2-di(ω- aminoalkyl)-2,6-dihydropyrazolo[3,4,5-kl]acridine-5-carboxamides. J. Med. Chem. 2001, 44, 3329.
    • (c) Antonini, I.; Polucci, P.; Magnano, A.; Sante, M. Synthesis, antitumor cytotoxicity, and DNA-binding of novel N-5,2-di(ω- aminoalkyl)-2,6-dihydropyrazolo[3,4,5-kl]acridine-5-carboxamides. J. Med. Chem. 2001, 44, 3329.
  • 10
    • 4644256896 scopus 로고    scopus 로고
    • The role of structural factors in the kinetics of cellular uptake of pyrazoloacridines and pyrazolopyrimidoacridines: Implications for overcoming multidrug resistance towards leukaemia K562/DOX cells
    • (a) Tarasiuk, J.; Majewska, E.; Seksek, O.; Rogacka, D.; Antonini, I.; Garnier-Suillerot, A.; Borowski, E. The role of structural factors in the kinetics of cellular uptake of pyrazoloacridines and pyrazolopyrimidoacridines: Implications for overcoming multidrug resistance towards leukaemia K562/DOX cells. Biochem. Pharmacol. 2004, 68, 1815;
    • (2004) Biochem. Pharmacol , vol.68 , pp. 1815
    • Tarasiuk, J.1    Majewska, E.2    Seksek, O.3    Rogacka, D.4    Antonini, I.5    Garnier-Suillerot, A.6    Borowski, E.7
  • 11
    • 0036214806 scopus 로고    scopus 로고
    • Tarasiuk, J.; Stefanska, B.; Pladzich, I.; Tkaczyk-Gobis, K.; Seksek, O.; Martelli, S.; Garnier-Suillerot, A.; Borowski, E. Anthrapyridones, a novel group of antitumour non-cross resistant anthraquinone analogues: Synthesis and molecular basis of the cytotoxic activity towards K562/DOX cells. Brit. J. Pharmacol. 2002, 135, 1513;
    • (b) Tarasiuk, J.; Stefanska, B.; Pladzich, I.; Tkaczyk-Gobis, K.; Seksek, O.; Martelli, S.; Garnier-Suillerot, A.; Borowski, E. Anthrapyridones, a novel group of antitumour non-cross resistant anthraquinone analogues: Synthesis and molecular basis of the cytotoxic activity towards K562/DOX cells. Brit. J. Pharmacol. 2002, 135, 1513;
  • 12
    • 0035895564 scopus 로고    scopus 로고
    • Transport of new non-cross-resistant antitumor compounds of the benzoperimidine family in multidrug resistant cells
    • (c) Tkaczyk-Gobis, K.; Tarasiuk, J.; Seksek, O.; Stefanska, B.; Borowski, E.; Garnier-Suillerot, A. Transport of new non-cross-resistant antitumor compounds of the benzoperimidine family in multidrug resistant cells. Eur. J. Pharmacol. 2001, 413, 131.
    • (2001) Eur. J. Pharmacol , vol.413 , pp. 131
    • Tkaczyk-Gobis, K.1    Tarasiuk, J.2    Seksek, O.3    Stefanska, B.4    Borowski, E.5    Garnier-Suillerot, A.6
  • 13
    • 0037245318 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of 2,7-dihydro-3H-dibenzo[de,h]cinnoline-3,7-dione derivatives, a novel group of anticancer agents active on a multidrug resistant cell line
    • (a) Stefanska, B.; Arciemiuk, M.; Bontemps-Gracz, M. M.; Dzieduszycka, M.; Kupiec, A.; Martelli, S.; Borowski, E. Synthesis and biological evaluation of 2,7-dihydro-3H-dibenzo[de,h]cinnoline-3,7-dione derivatives, a novel group of anticancer agents active on a multidrug resistant cell line. Bioorg. Med. Chem. 2003, 11, 561;
    • (2003) Bioorg. Med. Chem , vol.11 , pp. 561
    • Stefanska, B.1    Arciemiuk, M.2    Bontemps-Gracz, M.M.3    Dzieduszycka, M.4    Kupiec, A.5    Martelli, S.6    Borowski, E.7
  • 14
    • 0036166498 scopus 로고    scopus 로고
    • Effect of modification of 6-[(aminoalkyl)amino]-7H- benzo[e]-perimidin-7-ones on their cytotoxic activity toward sensitive and multidrug-resistant tumor cell lines. Synthesis and biological evaluation
    • (b) Dzieduszycka, M.; Martelli, S.; Arciemiuk, M.; Bontemps-Gracz, M. M.; Kupiec, A.; Borowski, E. Effect of modification of 6-[(aminoalkyl)amino]-7H- benzo[e]-perimidin-7-ones on their cytotoxic activity toward sensitive and multidrug-resistant tumor cell lines. Synthesis and biological evaluation. Bioorg. Med. Chem. 2002, 10, 1025;
    • (2002) Bioorg. Med. Chem , vol.10 , pp. 1025
    • Dzieduszycka, M.1    Martelli, S.2    Arciemiuk, M.3    Bontemps-Gracz, M.M.4    Kupiec, A.5    Borowski, E.6
  • 15
    • 0029135131 scopus 로고    scopus 로고
    • Antonini, I.; Cola, D.; Polucci, P.; Bontemps-Gracz, M. M.; Borowski, E.; Martelli, S. Synthesis of (dialkylamino)alkyl-disubstituted pyrimido[5,6,1-de]acridines, a novel group of anticancer agents active on a multidrug resistant Cell Line. J. Med. Chem. 1995, 38, 3282.
    • (c) Antonini, I.; Cola, D.; Polucci, P.; Bontemps-Gracz, M. M.; Borowski, E.; Martelli, S. Synthesis of (dialkylamino)alkyl-disubstituted pyrimido[5,6,1-de]acridines, a novel group of anticancer agents active on a multidrug resistant Cell Line. J. Med. Chem. 1995, 38, 3282.
  • 16
    • 8644274659 scopus 로고    scopus 로고
    • Bouffier, L.; Demeunynck, M.; Milet, A.; Dumy, P. Reactivity of pyrido[4,3,2-kl]acridines: Regioselective formation of 6-substituted derivatives. J. Org. Chem. 2004, 69, 8144;
    • (a) Bouffier, L.; Demeunynck, M.; Milet, A.; Dumy, P. Reactivity of pyrido[4,3,2-kl]acridines: Regioselective formation of 6-substituted derivatives. J. Org. Chem. 2004, 69, 8144;
  • 17
    • 85164051753 scopus 로고    scopus 로고
    • Fixler, N.; Demunynck, M.; Brochier, M.-C.; Garcia, J.; Lhomme, J. Regioselective addition of aniline to 8H-pyrido[ 2,3,4-mn] acridinone: Structure determination of the reaction product. Magn. Reson. Chem. 1997, 35, 697.
    • (b) Fixler, N.; Demunynck, M.; Brochier, M.-C.; Garcia, J.; Lhomme, J. Regioselective addition of aniline to 8H-pyrido[ 2,3,4-mn] acridinone: Structure determination of the reaction product. Magn. Reson. Chem. 1997, 35, 697.
  • 18
    • 0038305291 scopus 로고    scopus 로고
    • Pascual-Alfonso, E.; Avendano, C.; Menendez, J. C. Efficient synthesis of the pyrido[2,3,4-kl]acridin-4-one system common to several cytotoxic marine alkaloids. Tetrahedron Lett. 2003, 44, 6003.
    • Pascual-Alfonso, E.; Avendano, C.; Menendez, J. C. Efficient synthesis of the pyrido[2,3,4-kl]acridin-4-one system common to several cytotoxic marine alkaloids. Tetrahedron Lett. 2003, 44, 6003.
  • 19
    • 13844305773 scopus 로고    scopus 로고
    • Stefanska, B.; Bontemps-Gracz, M. M.; Antonini, I.; Martelli, S.; Arciemiuk, M.; Piwkowska, A.; Rogacka, D.; Borowski, E. 2,7-Dihydro-3H-pyridazino[ 5,4,3-kl]acridin-3-one derivatives, novel type of cytotoxic agents active on multidrug-resistant cell lines: Synthesis and biological evaluation. Bioorg. Med. Chem. 2005, 13, 1969.
    • Stefanska, B.; Bontemps-Gracz, M. M.; Antonini, I.; Martelli, S.; Arciemiuk, M.; Piwkowska, A.; Rogacka, D.; Borowski, E. 2,7-Dihydro-3H-pyridazino[ 5,4,3-kl]acridin-3-one derivatives, novel type of cytotoxic agents active on multidrug-resistant cell lines: Synthesis and biological evaluation. Bioorg. Med. Chem. 2005, 13, 1969.
  • 20
    • 3242778619 scopus 로고    scopus 로고
    • Delmas, F.; Avellaneda, A.; Giorgio, C. D.; Robin, M.; Clercq, E. D.; Timon-David, P.; Galy, J.-P. Synthesis and antileishmanial activity of (1,3-benzothiazol-2-yl) amino-9-(10H)-acridinone derivatives. Eur. J. Med. Chem. 2004, 39, 685.
    • Delmas, F.; Avellaneda, A.; Giorgio, C. D.; Robin, M.; Clercq, E. D.; Timon-David, P.; Galy, J.-P. Synthesis and antileishmanial activity of (1,3-benzothiazol-2-yl) amino-9-(10H)-acridinone derivatives. Eur. J. Med. Chem. 2004, 39, 685.
  • 21
    • 33947489306 scopus 로고
    • The chemistry of imines
    • (a) Layer, R. W. The chemistry of imines. Chem. Rev. 1963, 63, 489;
    • (1963) Chem. Rev , vol.63 , pp. 489
    • Layer, R.W.1
  • 22
    • 6544241298 scopus 로고
    • New Pd(II)- and Ni(II)-based catalysts for polymerization of ethylene and α-olefins
    • (b) Johnson, L. K.; Killian, C. M.; Brookhart, M. New Pd(II)- and Ni(II)-based catalysts for polymerization of ethylene and α-olefins. J. Am. Chem. Soc. 1995, 117, 6414;
    • (1995) J. Am. Chem. Soc , vol.117 , pp. 6414
    • Johnson, L.K.1    Killian, C.M.2    Brookhart, M.3
  • 23
    • 0034506322 scopus 로고    scopus 로고
    • Some evidence of a dual stereodifferentiation mechanism in the polymerization of propene by α-diimine nickel catalysts
    • (c) Pappalardo, D.; Mazzeo, M.; Antinucci, S.; Pellecchia, C. Some evidence of a dual stereodifferentiation mechanism in the polymerization of propene by α-diimine nickel catalysts. Macromolecules 2000, 33, 9483;
    • (2000) Macromolecules , vol.33 , pp. 9483
    • Pappalardo, D.1    Mazzeo, M.2    Antinucci, S.3    Pellecchia, C.4
  • 24
    • 15944378860 scopus 로고    scopus 로고
    • Ligand electronic effects on late transition metal polymerization catalysts
    • (d) Popeney, C.; Guan, Z. B. Ligand electronic effects on late transition metal polymerization catalysts. Organometallics 2005, 24, 1145.
    • (2005) Organometallics , vol.24 , pp. 1145
    • Popeney, C.1    Guan, Z.B.2
  • 25
    • 0037048609 scopus 로고    scopus 로고
    • Optical and photophysical properties of light-harvesting phenylacetylene monodendrons based on unsymmetrical branching
    • (a) Melinger, J. S.; Pan, Y.; Kleiman, V. D.; Peng, Z.; Davis, B. L.; McMorrow, D.; Lu, M. Optical and photophysical properties of light-harvesting phenylacetylene monodendrons based on unsymmetrical branching. J. Am. Chem. Soc. 2002, 124, 12002;
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 12002
    • Melinger, J.S.1    Pan, Y.2    Kleiman, V.D.3    Peng, Z.4    Davis, B.L.5    McMorrow, D.6    Lu, M.7
  • 26
    • 33746075555 scopus 로고    scopus 로고
    • Systematic studies on photoluminescence of oligo(aryleneethynylene) s: Tunability of excited states and derivatization as luminescent labeling probes for proteins
    • (b) Zhi, Y.-G.; Lai, S.-W.; Chan, Q. K.-W.; Law, Y.-C.; Tong, G. S.-M.; Che, C.-M. Systematic studies on photoluminescence of oligo(aryleneethynylene) s: Tunability of excited states and derivatization as luminescent labeling probes for proteins. Eur. J. Org. Chem. 2006, 3125.
    • (2006) Eur. J. Org. Chem , pp. 3125
    • Zhi, Y.-G.1    Lai, S.-W.2    Chan, Q.K.-W.3    Law, Y.-C.4    Tong, G.S.-M.5    Che, C.-M.6
  • 28
    • 3242885460 scopus 로고    scopus 로고
    • Synthesis and reactions of acenaphthenequinones - part-2: The reactions of acenaphthenequinones
    • (b) El Ashry, H. E. S.; Hamid, H. A.; Kassem, A. A.; Shoukry, M. Synthesis and reactions of acenaphthenequinones - part-2: The reactions of acenaphthenequinones. Molecules 2002, 7, 155.
    • (2002) Molecules , vol.7 , pp. 155
    • El Ashry, H.E.S.1    Hamid, H.A.2    Kassem, A.A.3    Shoukry, M.4
  • 33
    • 0141452964 scopus 로고    scopus 로고
    • WinGX suite for small-molecule single-crystal crystallography
    • Farrugia, L. J. WinGX suite for small-molecule single-crystal crystallography. J. Appl. Crystallogr. 1999, 32, 837.
    • (1999) J. Appl. Crystallogr , vol.32 , pp. 837
    • Farrugia, L.J.1
  • 34
    • 0003649817 scopus 로고    scopus 로고
    • ORTEP-III: Oak Ridge Thermal Ellipsoid Plot Program for crystal structure illustration
    • ORNL-6895, Oak Ridge, TN
    • Burnett, M. N.; Johnson, C. K. ORTEP-III: Oak Ridge Thermal Ellipsoid Plot Program for crystal structure illustration; (Oak Ridge National Laboratory Report ORNL-6895): Oak Ridge, TN, 1996.
    • (1996) Oak Ridge National Laboratory Report
    • Burnett, M.N.1    Johnson, C.K.2


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