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Volumn 123, Issue , 2016, Pages 704-717

Quinolino[3,4-b]quinoxalines and pyridazino[4,3-c]quinoline derivatives: Synthesis, inhibition of topoisomerase IIα, G-quadruplex binding and cytotoxic properties

Author keywords

Cytotoxic agents; G quadruplex stabilizers; Pyridazine derivatives; Quinoline derivatives; Topoisomerase II inhibitors

Indexed keywords

3 HYDROXY 3 (2 OXOPROPYL)QUINOLINE 2,4(1H,3H) DIONE; 3 METHYLPYRIDAZINO[4,3-C]QUINOLIN 5(6H) ONE; 5 (2 (DIETHYLAMINO)ETHYL)QUINOLINO[3,4-B]QUINOXALIN 6(5H) ONE; 5 (2 (DIMETHYLAMINO)ETHYL)QUINOLINO[3,4-B]QUINOXALIN 6(5H) ONE; 5 (2 (MORPHOLINOETHYL)ETHYL)QUINOLINO[3,4-B]QUINOXALIN 6(5H) ONE; 5 (3 (DIMETHYLAMINO)PROPYL)QUINOLINO[3,4-B]QUINOXALIN 6(5H) ONE; 5 (4 (DIMETHYLAMINO)BUTYL)QUINOLINO [3,4-B]QUINOXALIN 6(5H) ONE; 5 (4 CHLOROBUTYL)QUINOLINO[3,4-B] QUINOXALIN 6(5H) ONE; 6 (2 (DIMETHYLAMINO)ETHYL) 3 METHYLPYRIDAZINO[4,3-C]QUINOLIN 5(6H) ONE; 6 (2 MORPHOLINOETHOXY)QUINOLINO[3,4-B]QUINOXALINE; 6 CHLOROQUINOLINO[3,4-B]QUINOXALINE; DNA TOPOISOMERASE (ATP HYDROLYSING); DOXORUBICIN; GUANINE QUADRUPLEX; N (2 (DIETHYLAMINO)ETHYL)QUINOLINO[3,4-B]QUINOXALIN 6 AMINE; N (2 (DIETHYLAMINO)PROPYL)QUINOLINO[3,4-B]QUINOXALIN 6 AMINE; N (2 (DIMETHYLAMINO)ETHYL)QUINOLINO[3,4-B]QUINOXALIN 6 AMINE; N (2 (MORPHOLINOETHYL)QUINOLINO[3,4-B]QUINOXALIN 6 AMINE; N (2 (PIPERIDIN 1 YL)QUINOLINO[3,4-B]QUINOXALIN 6 AMINE; N (3 (DIMETHYLAMINO)PROPYL)QUINOLINO[3,4-B]QUINOXALIN 6 AMINE; N (4 (DIMETHYLAMINO)BUTYL)QUINOLINO[3,4-B]QUINOXALIN 6 AMINE; N (5 (N BENZYL N METHYLAMINO)PENTYL)QUINOLINO[3,4-B]QUINOXALIN 6 AMINE; N, N DIETHYL 3 (QUINOLINO[3,4-B]QUINOXALIN 6 YLOXY)ETHAMINE; N, N DIMETHYL 2 (QUINOLINO[3,4-B]QUINOXALIN 6 YLOXY)ETHANAMINE; N, N DIMETHYL 2 (QUINOLINO[3,4-B]QUINOXALIN 6 YLTHIO)ETHANAMINE; N, N DIMETHYL 3 (QUINOLINO[3,4-B]QUINOXALIN 6 YLOXY)PROPAN 1 AMINE; NOVOBIOCIN; QUINOLINE DERIVATIVE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ANTINEOPLASTIC AGENT; DNA BINDING PROTEIN; DNA TOPOISOMERASE II ALPHA; DNA TOPOISOMERASE IV; GYRASE INHIBITOR; TUMOR ANTIGEN;

EID: 84982843814     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2016.07.063     Document Type: Article
Times cited : (30)

References (42)
  • 2
    • 84906213465 scopus 로고    scopus 로고
    • DNA binders in clinical trials and chemotherapy
    • [2] Ali, A., Bhattacharya, S., DNA binders in clinical trials and chemotherapy. Bioorg. Med. Chem. 22 (2014), 4506–4521.
    • (2014) Bioorg. Med. Chem. , vol.22 , pp. 4506-4521
    • Ali, A.1    Bhattacharya, S.2
  • 3
    • 0037130278 scopus 로고    scopus 로고
    • Self-association and unique DNA binding properties of the anti-cancer agent TAS-103, a dual inhibitor of topoisomerases I and II
    • [3] Ishida, K., Asao, T., Self-association and unique DNA binding properties of the anti-cancer agent TAS-103, a dual inhibitor of topoisomerases I and II. Biochim. Biophys. Acta 1587 (2002), 155–163.
    • (2002) Biochim. Biophys. Acta , vol.1587 , pp. 155-163
    • Ishida, K.1    Asao, T.2
  • 5
    • 40849085407 scopus 로고    scopus 로고
    • A new mechanism of TAS-103 action discovered by target screening with drug immobilized affinity beads
    • [5] Yoshida, M., Kabe, Y., Wada, T., Asai, A., Handa, H., A new mechanism of TAS-103 action discovered by target screening with drug immobilized affinity beads. Mol. Pharmacol. 73 (2008), 987–994.
    • (2008) Mol. Pharmacol. , vol.73 , pp. 987-994
    • Yoshida, M.1    Kabe, Y.2    Wada, T.3    Asai, A.4    Handa, H.5
  • 6
    • 35348981766 scopus 로고    scopus 로고
    • Promising antitumor activity of a novel quinoline derivative, TAS-103, against fresh clinical specimens of eight types of tumors measured by flow cytometric DNA analysis
    • [6] Fujimoto, S., Promising antitumor activity of a novel quinoline derivative, TAS-103, against fresh clinical specimens of eight types of tumors measured by flow cytometric DNA analysis. Biol. Pharm. Bull. 30 (2007), 1923–1929.
    • (2007) Biol. Pharm. Bull. , vol.30 , pp. 1923-1929
    • Fujimoto, S.1
  • 9
    • 84900824121 scopus 로고    scopus 로고
    • Small-molecule quadruplex-targeted drug discovery
    • [9] Ohnmacht, S.A., Neidle, S., Small-molecule quadruplex-targeted drug discovery. Bioorg. Med. Chem. Lett. 24 (2014), 2602–2612.
    • (2014) Bioorg. Med. Chem. Lett. , vol.24 , pp. 2602-2612
    • Ohnmacht, S.A.1    Neidle, S.2
  • 10
    • 84883464255 scopus 로고    scopus 로고
    • Pharmacophore modeling and 3D-QSAR (CoMSIA) studies for structural requirements of some triazine derivatives as G-quadruplex binders for telomerase inhibition
    • [10] Zambre, V.P., Giridhar, R., Yadav, M.R., Pharmacophore modeling and 3D-QSAR (CoMSIA) studies for structural requirements of some triazine derivatives as G-quadruplex binders for telomerase inhibition. Med. Chem. Res. 22 (2013), 4685–4699.
    • (2013) Med. Chem. Res. , vol.22 , pp. 4685-4699
    • Zambre, V.P.1    Giridhar, R.2    Yadav, M.R.3
  • 11
    • 84886626805 scopus 로고    scopus 로고
    • G-quadruplex structures in the human genome as novel therapeutic targets
    • [11] Bidzinska, J., Cimino-Reale, G., Zaffaroni, N., Folini, M., G-quadruplex structures in the human genome as novel therapeutic targets. Molecules 18 (2013), 12368–12395.
    • (2013) Molecules , vol.18 , pp. 12368-12395
    • Bidzinska, J.1    Cimino-Reale, G.2    Zaffaroni, N.3    Folini, M.4
  • 12
    • 84899901387 scopus 로고    scopus 로고
    • G-quadruplex structures and their interaction diversity with ligands
    • [12] Zhang, S., Wu, Y., Zhang, W., G-quadruplex structures and their interaction diversity with ligands. ChemMedChem 9 (2014), 899–911.
    • (2014) ChemMedChem , vol.9 , pp. 899-911
    • Zhang, S.1    Wu, Y.2    Zhang, W.3
  • 15
    • 13944272246 scopus 로고    scopus 로고
    • The G-quadruplex-interactive molecule BRACO-19 inhibits tumor growth, consistent with telomere targeting and interference with telomerase function
    • [15] Burger, A.M., Dai, F., Schultes, C.M., Reszka, A.P., Moore, M.J., Double, J.A., Neidle, S., The G-quadruplex-interactive molecule BRACO-19 inhibits tumor growth, consistent with telomere targeting and interference with telomerase function. Cancer Res. 65 (2005), 1489–1496.
    • (2005) Cancer Res. , vol.65 , pp. 1489-1496
    • Burger, A.M.1    Dai, F.2    Schultes, C.M.3    Reszka, A.P.4    Moore, M.J.5    Double, J.A.6    Neidle, S.7
  • 17
    • 80051910937 scopus 로고    scopus 로고
    • Inhibition of cell proliferation by quindoline derivative (SYUIQ-05) through its preferential interaction with c-myc promoter G-quadruplex
    • [17] Ou, T.M., Lin, J., Lu, Y.J., Hou, J.Q., Tan, J.H., Chen, S.H., Li, Z., Li, Y.P., Li, D., Gu, L.Q., Huang, Z.S., Inhibition of cell proliferation by quindoline derivative (SYUIQ-05) through its preferential interaction with c-myc promoter G-quadruplex. J. Med. Chem. 54 (2011), 5671–5679.
    • (2011) J. Med. Chem. , vol.54 , pp. 5671-5679
    • Ou, T.M.1    Lin, J.2    Lu, Y.J.3    Hou, J.Q.4    Tan, J.H.5    Chen, S.H.6    Li, Z.7    Li, Y.P.8    Li, D.9    Gu, L.Q.10    Huang, Z.S.11
  • 18
    • 75849133718 scopus 로고    scopus 로고
    • Synthesis, cytotoxicity, antiviral activity and interferon inducing ability of 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxalines
    • [18] Shibinskay, M.O., Lyakhov, S.A., Mazepa, A.V., Andronati, S.A., Turov, A.V., Zholobak, N.M., Spivak, N.Y., Synthesis, cytotoxicity, antiviral activity and interferon inducing ability of 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxalines. Eur. J. Med. Chem. 45 (2010), 1237–1243.
    • (2010) Eur. J. Med. Chem. , vol.45 , pp. 1237-1243
    • Shibinskay, M.O.1    Lyakhov, S.A.2    Mazepa, A.V.3    Andronati, S.A.4    Turov, A.V.5    Zholobak, N.M.6    Spivak, N.Y.7
  • 23
    • 0032811376 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationships at the central benzodiazepine receptor of pyridazino[4,3-b]indoles and indeno[1,2-c]pyridazines
    • [23] Campagna, F., Palluotto, F., Carotti, A., Casini, G., Genchi, G., Synthesis and structure-activity relationships at the central benzodiazepine receptor of pyridazino[4,3-b]indoles and indeno[1,2-c]pyridazines. Bioorg. Med. Chem. 7 (1999), 1533–1538.
    • (1999) Bioorg. Med. Chem. , vol.7 , pp. 1533-1538
    • Campagna, F.1    Palluotto, F.2    Carotti, A.3    Casini, G.4    Genchi, G.5
  • 24
    • 0030454640 scopus 로고    scopus 로고
    • Structure-activity relationships of 2,5-dihydropyridazino[4,3-b]indol-3(3H)-ones at the benzodiazepine receptor
    • [24] Palluotto, F., Carotti, A., Casini, G., Genchi, G., Rizzo, M., De Sarro, G.B., Structure-activity relationships of 2,5-dihydropyridazino[4,3-b]indol-3(3H)-ones at the benzodiazepine receptor. Bioorg. Med. Chem. 4 (1996), 2091–2104.
    • (1996) Bioorg. Med. Chem. , vol.4 , pp. 2091-2104
    • Palluotto, F.1    Carotti, A.2    Casini, G.3    Genchi, G.4    Rizzo, M.5    De Sarro, G.B.6
  • 25
    • 85043117895 scopus 로고    scopus 로고
    • Organic electrochromic materials having high transparency and high contrast in the visible range, Patent WO2013/038243.
    • [25] G.A. Pagani, L. Beverina, M. Sassi, M. M. Salamone, C. M. Mari, R. Ruffo, Organic electrochromic materials having high transparency and high contrast in the visible range, Patent WO2013/038243.
    • Pagani, G.A.1    Beverina, L.2    Sassi, M.3    Salamone, M.M.4    Mari, C.M.5    Ruffo, R.6
  • 26
    • 0010611685 scopus 로고
    • Synthesen von Heterocyclen, 41. Mitt.: Über cyclische Dichlormalonyl-Verbindungen
    • [26] Ziegler, E., Salvador, R., Kappe, T., Synthesen von Heterocyclen, 41. Mitt.: Über cyclische Dichlormalonyl-Verbindungen. Monatsh. Chem. 93 (1962), 1376–1381.
    • (1962) Monatsh. Chem. , vol.93 , pp. 1376-1381
    • Ziegler, E.1    Salvador, R.2    Kappe, T.3
  • 27
    • 84878839300 scopus 로고
    • Chemistry of homophthalimide and 4-hydroxycarbostyril
    • [27] Fournier, C., Decombe, J., Chemistry of homophthalimide and 4-hydroxycarbostyril. Bull. Soc. Chim. Fr. 9 (1967), 3367–3371.
    • (1967) Bull. Soc. Chim. Fr. , vol.9 , pp. 3367-3371
    • Fournier, C.1    Decombe, J.2
  • 28
    • 30844456596 scopus 로고
    • Synthesen von Heterocyclen, 125 Mitt.: Über kondensierte Chinoxalinderivate
    • [28] Kappe, T., Reichel-Lender, E., Zeigler, E., Synthesen von Heterocyclen, 125 Mitt.: Über kondensierte Chinoxalinderivate. Monatsh. Chem. 100 (1969), 458–461.
    • (1969) Monatsh. Chem. , vol.100 , pp. 458-461
    • Kappe, T.1    Reichel-Lender, E.2    Zeigler, E.3
  • 29
    • 33947465799 scopus 로고
    • Aminolysis products of 1-chloro-2-hydroxy-3-butene, 1-hydroxy-2-chloro-3-butene and 1,2-epoxy-3-butene
    • [29] Blicke, F.F., Biel, J.H., Aminolysis products of 1-chloro-2-hydroxy-3-butene, 1-hydroxy-2-chloro-3-butene and 1,2-epoxy-3-butene. J. Am. Chem. Soc. 79 (1957), 5508–5512.
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 5508-5512
    • Blicke, F.F.1    Biel, J.H.2
  • 30
    • 0000212420 scopus 로고
    • Cyclic quaternary ammonium salts from halogenated aliphatic tertiary amines
    • [30] Littmann, E.R., Marvel, C.S., Cyclic quaternary ammonium salts from halogenated aliphatic tertiary amines. J. Am. Chem. Soc. 52 (1930), 287–294.
    • (1930) J. Am. Chem. Soc. , vol.52 , pp. 287-294
    • Littmann, E.R.1    Marvel, C.S.2
  • 31
    • 0004509035 scopus 로고
    • Synthesen von Heterocyclen, 118 Mitt.: Uber Reaktionem mit heterocyclischen Aminalen
    • [31] Kappe, T., Lendee, E., Ziegler, E., Synthesen von Heterocyclen, 118 Mitt.: Uber Reaktionem mit heterocyclischen Aminalen. Monatsh. Chem. 99 (1968), 2157–2166.
    • (1968) Monatsh. Chem. , vol.99 , pp. 2157-2166
    • Kappe, T.1    Lendee, E.2    Ziegler, E.3
  • 32
    • 0030014783 scopus 로고    scopus 로고
    • DNA topoisomerases
    • [32] Wang, J.C., DNA topoisomerases. Annu. Rev. Biochem. 65 (1996), 635–692.
    • (1996) Annu. Rev. Biochem. , vol.65 , pp. 635-692
    • Wang, J.C.1
  • 34
    • 77954187741 scopus 로고    scopus 로고
    • DNA topoisomerases and their poisoning by anticancer and antibacterial drugs
    • [34] Pommier, Y., Leo, E., Zhang, H., Marchand, C., DNA topoisomerases and their poisoning by anticancer and antibacterial drugs. Chem. Biol. 17 (2010), 421–433.
    • (2010) Chem. Biol. , vol.17 , pp. 421-433
    • Pommier, Y.1    Leo, E.2    Zhang, H.3    Marchand, C.4
  • 35
    • 84881660081 scopus 로고    scopus 로고
    • Distinct regions of the Escherichia coli ParC C-terminal domain are required for substrate discrimination by topoisomerase IV
    • [35] Vos, S.M., Lee, I., Berger, J.M., Distinct regions of the Escherichia coli ParC C-terminal domain are required for substrate discrimination by topoisomerase IV. J. Mol. Biol. 425 (2013), 3029–3045.
    • (2013) J. Mol. Biol. , vol.425 , pp. 3029-3045
    • Vos, S.M.1    Lee, I.2    Berger, J.M.3
  • 36
    • 47249089630 scopus 로고    scopus 로고
    • Polymorphism of human telomeric quadruplex structures
    • [36] Dai, J., Carver, M., Yang, D., Polymorphism of human telomeric quadruplex structures. Biochimie 90 (2008), 1172–1183.
    • (2008) Biochimie , vol.90 , pp. 1172-1183
    • Dai, J.1    Carver, M.2    Yang, D.3
  • 37
    • 79953313413 scopus 로고    scopus 로고
    • Targeting G-quadruplexes in gene promoters: a novel anticancer strategy?
    • [37] Balasubramanian, S., Hurley, L.H., Neidle, S., Targeting G-quadruplexes in gene promoters: a novel anticancer strategy?. Nat. Rev. Drug Discov. 10 (2011), 261–275.
    • (2011) Nat. Rev. Drug Discov. , vol.10 , pp. 261-275
    • Balasubramanian, S.1    Hurley, L.H.2    Neidle, S.3
  • 38
    • 79960700683 scopus 로고    scopus 로고
    • Fluorescence intercalator displacement assay for screening G4 ligands towards a variety of G-quadruplex structures
    • [38] Tran, P.L., Largy, E., Hamon, F., Teulade-Fichou, M.P., Mergny, J.L., Fluorescence intercalator displacement assay for screening G4 ligands towards a variety of G-quadruplex structures. Biochimie 93 (2011), 1288–1296.
    • (2011) Biochimie , vol.93 , pp. 1288-1296
    • Tran, P.L.1    Largy, E.2    Hamon, F.3    Teulade-Fichou, M.P.4    Mergny, J.L.5
  • 39
    • 77954110151 scopus 로고    scopus 로고
    • Rational design, synthesis, and DNA binding properties of novel sequence-selective peptidyl congeners of ametantrone
    • [39] Gianoncelli, A., Basili, S., Scalabrin, M., Sosic, A., Moro, S., Zagotto, G., Palumbo, M., Gresh, N., Gatto, B., Rational design, synthesis, and DNA binding properties of novel sequence-selective peptidyl congeners of ametantrone. ChemMedChem 5 (2010), 1080–1091.
    • (2010) ChemMedChem , vol.5 , pp. 1080-1091
    • Gianoncelli, A.1    Basili, S.2    Scalabrin, M.3    Sosic, A.4    Moro, S.5    Zagotto, G.6    Palumbo, M.7    Gresh, N.8    Gatto, B.9
  • 40
    • 84884950457 scopus 로고    scopus 로고
    • Synthesis, G-quadruplex stabilisation, docking studies, and effect on cancer cells of indolo[3,2-b]quinolines with one, two, or three basic side chains
    • [40] Lavrado, J., Borralho, P.M., Ohnmacht, S.A., Castro, R.E., Rodrigues, C.M.P., Moreira, R., dos Santos, D.J.V.A., Neidle, S., Paulo, A., Synthesis, G-quadruplex stabilisation, docking studies, and effect on cancer cells of indolo[3,2-b]quinolines with one, two, or three basic side chains. ChemMedChem 8 (2013), 1648–1661.
    • (2013) ChemMedChem , vol.8 , pp. 1648-1661
    • Lavrado, J.1    Borralho, P.M.2    Ohnmacht, S.A.3    Castro, R.E.4    Rodrigues, C.M.P.5    Moreira, R.6    dos Santos, D.J.V.A.7    Neidle, S.8    Paulo, A.9


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