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Volumn 57, Issue 4, 2014, Pages 1390-1402

Optimization of 4-(N-cycloamino)phenylquinazolines as a novel class of tubulin-polymerization inhibitors targeting the colchicine site

Author keywords

[No Author keywords available]

Indexed keywords

2 CHLORO 4 [N (5 METHOXY)INDOLINYL]QUINAZOLINE; 2 CHLORO 4 [N (6 METHOXY 2,3 DIHYDRO 4 OXOQUINOLINYL)]QUINAZOLINE; 2 CHLORO 4 [N (6 METHYL 3,4 DIHYDROQUINOLINYL)]QUINAZOLINE; 2 CHLORO 4 [N (7 METHOXY 2,3,4,5 TETRAHYDRO 1H BENZO[B]AZEPINYL)]QUINAZOLINE; 2 CHLORO 4 [N (7 METHOXY 2,3,4,5 TETRAHYDRO 1H BENZO[C]AZEPINYL)]QUINAZOLINE; 2 CHLORO 4 [N (7 METHOXY 3,4 DIHYDRO 2H BENZO[B][1,4]OXAZINYL)]QUINAZOLINE; 2 METHYL 4 (1 METHYL 7 METHOXY 2 OXO 3,4 DIHYDROQUINOXALIN 4 YL)QUINAZOLINE; 2 METHYL 4 [N (6 METHYL 1,2,3,4 TETRAHYDROQUINOLINYL)]QUINAZOLINE; 2 METHYL 4 [N (7 METHOXY 3,4 DIHYDRO 2H BENZO[B][1,4]OXAZINYL)]QUINAZOLINE; 4 (N CYCLOAMINO)PHENYLQUINAZOLINE DERIVATIVE; 4 [N (5 METHOXY)INDOLINYL] 2 METHYLQUINAZOLINE; 4 [N (6 BROMO 1,2,3,4 TETRAHYDROQUINOLINYL)] 2 METHYLQUINAZOLINE; 4 [N (6 METHOXY 2,3 DIHYDRO 4 OXOQUINOLINYL)] 2 METHYLQUINAZOLINE; 4 [N (7 METHOXY 2,3,4,5 TETRAHYDRO 1H BENZO[B]AZEPINYL)] 2 METHYLQUINAZOLINE; 4 [N (7 METHOXY 2,3,4,5 TETRAHYDRO 1H BENZO[C]AZEPINYL)] 2 METHYLQUINAZOLINE; 7 METHOXY 4 (2 METHYLQUINAZOLIN 4 YL) 3,4 DIHYDROQUINOXALIN 2(1H) ONE; ANTINEOPLASTIC AGENT; COLCHICINE; PACLITAXEL; PROPRANOLOL; QUINAZOLINE DERIVATIVE; TERFENADINE; UNCLASSIFIED DRUG;

EID: 84896876455     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm4016526     Document Type: Article
Times cited : (64)

References (37)
  • 1
    • 77957374075 scopus 로고    scopus 로고
    • Microtubule-binding agents: A dynamic field of cancer therapeutics
    • Dumontet, C.; Jordan, M. A. Microtubule-binding agents: A dynamic field of cancer therapeutics Nat. Rev. Drug Discovery 2010, 9, 790-803
    • (2010) Nat. Rev. Drug Discovery , vol.9 , pp. 790-803
    • Dumontet, C.1    Jordan, M.A.2
  • 2
    • 78649833819 scopus 로고    scopus 로고
    • The unique characteristics of tumor vasculature and preclinical evidence for its selective disruption by tumor-vascular disrupting agents
    • Siemann, D. W. The unique characteristics of tumor vasculature and preclinical evidence for its selective disruption by tumor-vascular disrupting agents Cancer Treat. Rev. 2011, 37, 63-74
    • (2011) Cancer Treat. Rev. , vol.37 , pp. 63-74
    • Siemann, D.W.1
  • 4
    • 79953741443 scopus 로고    scopus 로고
    • A perspective on vascular disrupting agents that interact with tubulin: Preclinical tumor imaging and biological assessment
    • Mason, R. P.; Zhao, D.; Liu, L.; Trawick, M. L.; Pinney, K. G. A perspective on vascular disrupting agents that interact with tubulin: Preclinical tumor imaging and biological assessment Integr. Biol. 2011, 3, 375-387
    • (2011) Integr. Biol. , vol.3 , pp. 375-387
    • Mason, R.P.1    Zhao, D.2    Liu, L.3    Trawick, M.L.4    Pinney, K.G.5
  • 5
    • 84922686916 scopus 로고    scopus 로고
    • Vascular disrpting agents targeting at tubulin: A novel class of antitumor drug
    • Wang, X. F.; Xie, L. Vascular disrpting agents targeting at tubulin: A novel class of antitumor drug J. Int. Pharm. Res. 2012, 39, 445-454
    • (2012) J. Int. Pharm. Res. , vol.39 , pp. 445-454
    • Wang, X.F.1    Xie, L.2
  • 9
    • 84872303107 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of N -alkyl- N -(4-methoxyphenyl) pyridin-2-amines as a new class of tubulin polymerization inhibitors
    • Wang, X. F.; Ohkoshi, E.; Wang, S. B.; Hamel, E.; Bastow, K. F.; Morris-Natschke, S. L.; Lee, K. H.; Xie, L. Synthesis and biological evaluation of N -alkyl- N -(4-methoxyphenyl)pyridin-2-amines as a new class of tubulin polymerization inhibitors Bioorg. Med. Chem. 2013, 21, 632-642
    • (2013) Bioorg. Med. Chem. , vol.21 , pp. 632-642
    • Wang, X.F.1    Ohkoshi, E.2    Wang, S.B.3    Hamel, E.4    Bastow, K.F.5    Morris-Natschke, S.L.6    Lee, K.H.7    Xie, L.8
  • 10
    • 84882536698 scopus 로고    scopus 로고
    • N -Aryl-6-methoxy-1,2,3,4-tetrahydroquinolines: A novel class of antitumor agents targeting the colchicine site on tubulin
    • Wang, X. F.; Wang, S. B.; Ohkoshi, E.; Wang, L. T.; Hamel, E.; Qian, K.; Morris-Natschke, S. L.; Lee, K. H.; Xie, L. N -Aryl-6-methoxy-1,2,3,4- tetrahydroquinolines: A novel class of antitumor agents targeting the colchicine site on tubulin Eur. J. Med. Chem. 2013, 67, 196-207
    • (2013) Eur. J. Med. Chem. , vol.67 , pp. 196-207
    • Wang, X.F.1    Wang, S.B.2    Ohkoshi, E.3    Wang, L.T.4    Hamel, E.5    Qian, K.6    Morris-Natschke, S.L.7    Lee, K.H.8    Xie, L.9
  • 11
    • 4143066760 scopus 로고    scopus 로고
    • Gefitinib-sensitizing EGFR mutations in lung cancer activate anti-apoptotic pathways
    • Sordella, R.; Bell, D. W.; Haber, D. A.; Settleman, J. Gefitinib-sensitizing EGFR mutations in lung cancer activate anti-apoptotic pathways Science 2004, 305, 1163-1167
    • (2004) Science , vol.305 , pp. 1163-1167
    • Sordella, R.1    Bell, D.W.2    Haber, D.A.3    Settleman, J.4
  • 15
    • 85010143353 scopus 로고
    • A convenient synthesis of monocyclic β -lactams by means of solid-liquid phase transfer reactions
    • Takahata, H.; Ohnishi, Y.; Takehara, H.; Tsuritani, K.; Yamazaki, T. A convenient synthesis of monocyclic β -lactams by means of solid-liquid phase transfer reactions Chem. Pharm. Bull. 1981, 29, 1063-1068
    • (1981) Chem. Pharm. Bull. , vol.29 , pp. 1063-1068
    • Takahata, H.1    Ohnishi, Y.2    Takehara, H.3    Tsuritani, K.4    Yamazaki, T.5
  • 16
    • 0010654220 scopus 로고    scopus 로고
    • The first intermolecular Friedel-Crafts acylation with β-lactams
    • Anderson, K. W.; Tepe, J. J. The first intermolecular Friedel-Crafts acylation with β-lactams Org. Lett. 2002, 4, 459-461
    • (2002) Org. Lett. , vol.4 , pp. 459-461
    • Anderson, K.W.1    Tepe, J.J.2
  • 17
    • 0023102144 scopus 로고
    • Synthesis of D-oxa tricyclic partial ergolines as dopamine agonists
    • Booher, R. N.; Kornfeld, E. C.; Smalstig, E. B.; Clemens, J. A. Synthesis of D-oxa tricyclic partial ergolines as dopamine agonists J. Med. Chem. 1987, 30, 580-583
    • (1987) J. Med. Chem. , vol.30 , pp. 580-583
    • Booher, R.N.1    Kornfeld, E.C.2    Smalstig, E.B.3    Clemens, J.A.4
  • 18
    • 0032730818 scopus 로고    scopus 로고
    • Synthesis of oxypropanolamine derivatives of 3,4-dihydro-2H-1,4- benzoxazine, β-adrenergic affinity, inotropic, chronotropic and coronary vasodilating activities
    • Iakovou, K.; Kazanis, M.; Vavayannis, A.; Bruni, G.; Romeo, M. R.; Massarelli, P.; Teramoto, S.; Fujiki, H.; Mori, T. Synthesis of oxypropanolamine derivatives of 3,4-dihydro-2H-1,4-benzoxazine, β-adrenergic affinity, inotropic, chronotropic and coronary vasodilating activities Eur. J. Med. Chem. 1999, 34, 903-917
    • (1999) Eur. J. Med. Chem. , vol.34 , pp. 903-917
    • Iakovou, K.1    Kazanis, M.2    Vavayannis, A.3    Bruni, G.4    Romeo, M.R.5    Massarelli, P.6    Teramoto, S.7    Fujiki, H.8    Mori, T.9
  • 19
    • 0031059045 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of nonclassical 2,4-diamino-5- methylpyrido[2,3-d]pyrimidines with novel side chain substituents as potential inhibitors of dihydrofolate reductases1
    • Gangjee, A.; Vasudevan, A.; Queener, S. F. Synthesis and biological evaluation of nonclassical 2,4-diamino-5-methylpyrido[2,3-d]pyrimidines with novel side chain substituents as potential inhibitors of dihydrofolate reductases1 J. Med. Chem. 1997, 40, 479-485
    • (1997) J. Med. Chem. , vol.40 , pp. 479-485
    • Gangjee, A.1    Vasudevan, A.2    Queener, S.F.3
  • 20
    • 40749142752 scopus 로고    scopus 로고
    • SAR studies of capsazepinoid bronchodilators. Part 1: The importance of the catechol moiety and aspects of the B-ring structure
    • Dalence-Guzmán, M. F.; Berglund, M.; Skogvall, S.; Sterner, O. SAR studies of capsazepinoid bronchodilators. Part 1: The importance of the catechol moiety and aspects of the B-ring structure Bioorg. Med. Chem. 2008, 16, 2499-2512
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 2499-2512
    • Dalence-Guzmán, M.F.1    Berglund, M.2    Skogvall, S.3    Sterner, O.4
  • 22
    • 84862285321 scopus 로고    scopus 로고
    • Antitumor agents. 293. Nontoxic dimethyl-4,4′-dimethoxy-5,6, 5′,6′-dimethylenedioxybiphenyl-2,2′- dicarboxylate (DDB) analogues chemosensitize multidrug-resistant cancer cells to clinical anticancer drugs
    • Hung, H. Y.; Ohkoshi, E.; Goto, M.; Bastow, K. F.; Nakagawa-Goto, K.; Lee, K. H. Antitumor agents. 293. Nontoxic dimethyl-4,4′-dimethoxy-5,6, 5′,6′-dimethylenedioxybiphenyl-2,2′- dicarboxylate (DDB) analogues chemosensitize multidrug-resistant cancer cells to clinical anticancer drugs J. Med. Chem. 2012, 55, 5413-5424
    • (2012) J. Med. Chem. , vol.55 , pp. 5413-5424
    • Hung, H.Y.1    Ohkoshi, E.2    Goto, M.3    Bastow, K.F.4    Nakagawa-Goto, K.5    Lee, K.H.6
  • 23
    • 0025367455 scopus 로고
    • Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines
    • Rubinstein, L. V.; Shoemaker, R. H.; Paull, K. D.; Simon, R. M.; Tosini, S.; Skehan, P.; Scudiero, D. A.; Monks, A.; Boyd, M. R. Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines J. Natl. Cancer Inst. 1990, 82, 1113-1117
    • (1990) J. Natl. Cancer Inst. , vol.82 , pp. 1113-1117
    • Rubinstein, L.V.1    Shoemaker, R.H.2    Paull, K.D.3    Simon, R.M.4    Tosini, S.5    Skehan, P.6    Scudiero, D.A.7    Monks, A.8    Boyd, M.R.9
  • 24
    • 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
    • Lin, C. M.; Ho, H. H.; Pettit, G. R.; Hamel, E. 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 1989, 28, 6984-6991
    • (1989) Biochemistry , vol.28 , pp. 6984-6991
    • Lin, C.M.1    Ho, H.H.2    Pettit, G.R.3    Hamel, E.4
  • 26
    • 79955432079 scopus 로고    scopus 로고
    • MT119, a new planar-structured compound, targets the colchicine site of tubulin arresting mitosis and inhibiting tumor cell proliferation
    • Zhang, Z.; Meng, T.; Yang, N.; Wang, W.; Xiong, B.; Chen, Y.; Ma, L.; Shen, J.; Miao, Z. H.; Ding, J. MT119, a new planar-structured compound, targets the colchicine site of tubulin arresting mitosis and inhibiting tumor cell proliferation Int. J. Cancer 2011, 129, 214-224
    • (2011) Int. J. Cancer , vol.129 , pp. 214-224
    • Zhang, Z.1    Meng, T.2    Yang, N.3    Wang, W.4    Xiong, B.5    Chen, Y.6    Ma, L.7    Shen, J.8    Miao, Z.H.9    Ding, J.10
  • 27
    • 1642401199 scopus 로고    scopus 로고
    • Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain
    • Knossow, M.; Jourdain, I.; Lachkar, S. Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain Nature 2004, 428, 198-202
    • (2004) Nature , vol.428 , pp. 198-202
    • Knossow, M.1    Jourdain, I.2    Lachkar, S.3
  • 29
    • 84866918553 scopus 로고    scopus 로고
    • Design, synthesis, and preclinical evaluations of novel 4-substituted 1,5-diarylanilines as potent HIV-1 non-nucleoside reverse transcriptase inhibitor (NNRTI) drug candidates
    • Sun, L. Q.; Zhu, L.; Qian, K.; Qin, B.; Huang, L.; Chen, C. H.; Lee, K. H.; Xie, L. Design, synthesis, and preclinical evaluations of novel 4-substituted 1,5-diarylanilines as potent HIV-1 non-nucleoside reverse transcriptase inhibitor (NNRTI) drug candidates J. Med. Chem. 2012, 55, 7219-7229
    • (2012) J. Med. Chem. , vol.55 , pp. 7219-7229
    • Sun, L.Q.1    Zhu, L.2    Qian, K.3    Qin, B.4    Huang, L.5    Chen, C.H.6    Lee, K.H.7    Xie, L.8
  • 30
    • 0000719887 scopus 로고
    • Status of the NCI preclinical antitumor drug discovery screen
    • Devita, V. T. Hellman, S. Rosenberg, S. A. J. B. Lippincott: Philadelphia, PA
    • Boyd, M. R. Status of the NCI preclinical antitumor drug discovery screen. In Cancer: Principles and Practice of Oncology Updates; Devita, V. T.; Hellman, S.; Rosenberg, S. A., Eds.; J. B. Lippincott: Philadelphia, PA, 1989; pp 1-12.
    • (1989) Cancer: Principles and Practice of Oncology Updates , pp. 1-12
    • Boyd, M.R.1
  • 32
    • 34249850360 scopus 로고    scopus 로고
    • The sulphorhodamine (SRB) assay and other approaches to testing plant extracts and derived compounds for activities related to reputed anticancer activity
    • Houghton, P.; Fang, R.; Techatanawat, I.; Steventon, G.; Hylands, P. J.; Lee, C. C. The sulphorhodamine (SRB) assay and other approaches to testing plant extracts and derived compounds for activities related to reputed anticancer activity Methods 2007, 42, 377-387
    • (2007) Methods , vol.42 , pp. 377-387
    • Houghton, P.1    Fang, R.2    Techatanawat, I.3    Steventon, G.4    Hylands, P.J.5    Lee, C.C.6
  • 33
    • 0142036683 scopus 로고    scopus 로고
    • Evaluation of antimitotic agents by quantitative comparisons of their effects on the polymerization of purified tubulin
    • Hamel, E. Evaluation of antimitotic agents by quantitative comparisons of their effects on the polymerization of purified tubulin Cell Biochem. Biophys. 2003, 38, 1-22
    • (2003) Cell Biochem. Biophys. , vol.38 , pp. 1-22
    • Hamel, E.1
  • 34
    • 0031913357 scopus 로고    scopus 로고
    • Structure-activity analysis of the interaction of curacin A, the potent colchicine site antimitotic agent, with tubulin and effects of analogs on the growth of MCF-7 breast cancer cells
    • Verdier-Pinard, P.; Lai, J.-Y.; Yoo, H.-D.; Yu, J.; Márquez, B.; Nagle, D. G.; Nambu, M.; White, J. D.; Falck, J. R.; Gerwick, W. H.; Day, B. W.; Hamel, E. Structure-activity analysis of the interaction of curacin A, the potent colchicine site antimitotic agent, with tubulin and effects of analogs on the growth of MCF-7 breast cancer cells Mol. Pharmacol. 1998, 53, 62-76
    • (1998) Mol. Pharmacol. , vol.53 , pp. 62-76
    • Verdier-Pinard, P.1    Lai, J.-Y.2    Yoo, H.-D.3    Yu, J.4    Márquez, B.5    Nagle, D.G.6    Nambu, M.7    White, J.D.8    Falck, J.R.9    Gerwick, W.H.10    Day, B.W.11    Hamel, E.12
  • 36
    • 0019513433 scopus 로고
    • Glutamate-induced polymerization of tubulin: Characteristics of the reaction and application to the large-scale purification of tubulin
    • Hamel, E.; Lin, C. M. Glutamate-induced polymerization of tubulin: Characteristics of the reaction and application to the large-scale purification of tubulin Arch. Biochem. Biophys. 1981, 209, 29-40
    • (1981) Arch. Biochem. Biophys. , vol.209 , pp. 29-40
    • Hamel, E.1    Lin, C.M.2
  • 37
    • 0008891824 scopus 로고
    • Promotion of fluorescence upon binding of colchicine to tubulin
    • Bhattacharyya, B.; Wolff, J. Promotion of fluorescence upon binding of colchicine to tubulin Proc. Natl. Acad. Sci. U.S.A. 1974, 71, 2627-2631
    • (1974) Proc. Natl. Acad. Sci. U.S.A. , vol.71 , pp. 2627-2631
    • Bhattacharyya, B.1    Wolff, J.2


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