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Volumn 54, Issue 14, 2011, Pages 4977-4986

Regioselective Suzuki coupling of dihaloheteroaromatic compounds as a rapid strategy to synthesize potent rigid combretastatin analogues

Author keywords

[No Author keywords available]

Indexed keywords

2 (4 METHOXYPHENYL) 3 (3,4,5 TRIMETHOXYPHENYL)FURAN; 2 METHOXY 5 [2 (3,4,5 TRIMETHOXYPHENYL) 3 FURYL]PHENOL; 2 METHOXY 5 [2 (3,4,5 TRIMETHOXYPHENYL)CYCLOPENT 1 EN 1 YL]PHENOL; 2 METHOXY 5 [3 (3,4,5 TRIMETHOXYPHENYL) 2 FURYL]PHENOL; 3 (4 METHOXYPHENYL) 2 (3,4,5 TRIMETHOXYPHENYL)FURAN; 3 BROMO 2 (4 METHOXYPHENYL)FURAN; ALICYCLIC COMPOUND; AROMATIC COMPOUND; COMBRETASTATIN; COMBRETASTATIN A4; CYCLOPENTENE DERIVATIVE; FURAN DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 79960627839     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200555r     Document Type: Article
Times cited : (94)

References (33)
  • 1
    • 0024513175 scopus 로고
    • Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A-4
    • DOI 10.1007/BF01954881
    • Pettit, G. R.; Singh, S. B.; Hamel, E.; Lin, C. M.; Alberts, D. S. Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A-4 Experientia 1989, 45, 209-211 (Pubitemid 19062390)
    • (1989) Experientia , vol.45 , Issue.2 , 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
  • 2
    • 0036324971 scopus 로고    scopus 로고
    • Combretastatin anticancer drugs
    • DOI 10.1358/dof.2002.027.05.668645
    • Bibby, M. C. Combretastatin anticancer drugs Drugs Future 2002, 27, 475-480 (Pubitemid 34815035)
    • (2002) Drugs of the Future , vol.27 , Issue.5 , pp. 475-480
    • Bibby, M.C.1
  • 3
    • 85008389252 scopus 로고    scopus 로고
    • The Discovery and Development of the Combretastatins
    • In; Kingston, D.; Newman, D.; Cragg, G., Eds.; CRC Press: Boca Raton, FL
    • Pinney, K. G.; Jelinek, C.; Edvardsen, K.; Chaplin, D. J.; Pettit, G. R. The Discovery and Development of the Combretastatins. In Antitumor Agents from Natural Products; Kingston, D.; Newman, D.; Cragg, G., Eds.; CRC Press: Boca Raton, FL, 2005; pp 23-46.
    • (2005) Antitumor Agents from Natural Products , pp. 23-46
    • Pinney, K.G.1    Jelinek, C.2    Edvardsen, K.3    Chaplin, D.J.4    Pettit, G.R.5
  • 4
    • 0037085753 scopus 로고    scopus 로고
    • The tumor vascular targeting agent combretastatin A-4-phosphate induces reorganization of the actin cytoskeleton and early membrane blebbing in human endothelial cells
    • DOI 10.1182/blood.V99.6.2060
    • Kanthou, C.; Tozer, G. M. The tumor vascular targeting agent combretastatin A-4 phosphate induces reorganization of the actin cytoskeleton and early membrane blebbing in human endothelial cells Blood 2002, 99, 2060-2069 (Pubitemid 34525489)
    • (2002) Blood , vol.99 , Issue.6 , pp. 2060-2069
    • Kanthou, C.1    Tozer, G.M.2
  • 5
    • 0036891515 scopus 로고    scopus 로고
    • The development of combretastatin A4 phosphate as a vascular targeting agent
    • DOI 10.1016/S0360-3016(02)03924-X, PII S036030160203924X
    • Chaplin, D. J.; Hill, S. A. The development of combretastatin A-4 phosphate as a vascular targeting agent Int. J. Radiat. Oncol., Biol., Phys. 2002, 54, 1491-1496 (Pubitemid 35380054)
    • (2002) International Journal of Radiation Oncology Biology Physics , vol.54 , Issue.5 , pp. 1491-1496
    • Chaplin, D.J.1    Hill, S.A.2
  • 6
    • 1842607060 scopus 로고    scopus 로고
    • Combretastatin A4 phosphate
    • West, C. M. L.; Price, P. Combretastatin A4 phosphate Anti-Cancer Drugs 2004, 15, 179-186
    • (2004) Anti-Cancer Drugs , vol.15 , pp. 179-186
    • West, C.M.L.1    Price, P.2
  • 7
    • 65549090459 scopus 로고    scopus 로고
    • A review and update of the current status of the vasculature-disabling agent combretastatin-A4 phosphate (CA4P)
    • Siemann, D. W.; Chaplin, D. J.; Walicke, P. A. A review and update of the current status of the vasculature-disabling agent combretastatin-A4 phosphate (CA4P) Expert Opin. Invest. Drugs 2009, 18, 189-197
    • (2009) Expert Opin. Invest. Drugs , vol.18 , pp. 189-197
    • Siemann, D.W.1    Chaplin, D.J.2    Walicke, P.A.3
  • 8
    • 70349338935 scopus 로고    scopus 로고
    • AVE8062: A new combretastatin derivative vascular disrupting agent
    • Delmonte, A.; Sessa, C. AVE8062: a new combretastatin derivative vascular disrupting agent Expert Opin. Invest. Drugs 2009, 18, 1541-1548
    • (2009) Expert Opin. Invest. Drugs , vol.18 , pp. 1541-1548
    • Delmonte, A.1    Sessa, C.2
  • 10
    • 0141518578 scopus 로고    scopus 로고
    • Structural requirements for the interaction of combretastatins with tubulin: How important is the trimethoxy unit?
    • Gaukroger, K.; Hadfield, J. A.; Lawrence, N. J.; Nlan, S.; McGown, A. T. Structural requirements for the interaction of combretastatins with tubulin: How important is the trimethoxy unit? Org. Biomol. Chem. 2003, 1, 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
  • 12
    • 36349000649 scopus 로고    scopus 로고
    • In vitro metabolism study of combretastatin A-4 in rat and human liver microsomes
    • DOI 10.1124/dmd.107.016998
    • Aprile, S.; Del Grosso, E.; Tron, G. C.; Grosa, G. In vitro metabolism study of combretastatin A-4 in rat and human liver microsomes Drug Metab. Dispos. 2007, 35, 2252-2261 (Pubitemid 350146212)
    • (2007) Drug Metabolism and Disposition , vol.35 , Issue.12 , pp. 2252-2261
    • Aprile, S.1    Del Grosso, E.2    Tron, G.C.3    Grosa, G.4
  • 13
    • 0041421003 scopus 로고    scopus 로고
    • Combretastatin A-4 analogues as antimitotic antitumor agents
    • DOI 10.2174/0929867033457151
    • Nam, N.-H. Combretastatin A-4 analogues as antimitotic antitumor agents Curr. Med. Chem. 2003, 10, 1697-1722 (Pubitemid 37038595)
    • (2003) Current Medicinal Chemistry , vol.10 , Issue.17 , pp. 1697-1722
    • Nam, N.-H.1
  • 23
    • 33645454183 scopus 로고    scopus 로고
    • A simple guide for predicting regioselectivity in the coupling of polyhaloheteroaromatics
    • Handy, S. T.; Zhang, Y. A simple guide for predicting regioselectivity in the coupling of polyhaloheteroaromatics Chem. Commun. 2006, 299-301
    • (2006) Chem. Commun. , pp. 299-301
    • Handy, S.T.1    Zhang, Y.2
  • 25
    • 25144434945 scopus 로고    scopus 로고
    • Structure-based discovery of a boronic acid bioisostere of combretastatin A-4
    • DOI 10.1016/j.chembiol.2005.06.016, PII S1074552105002334
    • Kong, Y.; Grembecka, J.; Edler, M. C.; Hamel, E.; Mooberry, S.; Sabat, M.; Rieger, J.; Brown, M. L. Structure-based discovery of a boronic acid bioisostere of combretastatin A-4 Chem. Biol. 2005, 12, 1007-1014 (Pubitemid 41338811)
    • (2005) Chemistry and Biology , vol.12 , Issue.9 , pp. 1007-1014
    • Kong, Y.1    Grembecka, J.2    Edler, M.C.3    Hamel, E.4    Mooberry, S.L.5    Sabat, M.6    Rieger, J.7    Brown, M.L.8
  • 27
    • 0025872827 scopus 로고
    • Resistance to antimitotic drugs in Chinese hamster ovary cells correlates with changes in the level of polymerized tubulin
    • Minotti, A. M.; Barlow, S. B.; Cabral, F. Resistance to antimitotic drugs in Chinese hamster ovary cells correlates with changes in the level of polymerized tubulin J. Biol. Chem. 1991, 266, 3987-3994 (Pubitemid 21909306)
    • (1991) Journal of Biological Chemistry , vol.266 , Issue.6 , pp. 3987-3994
    • Minotti, A.M.1    Barlow, S.B.2    Cabral, F.3
  • 28
    • 1642281756 scopus 로고    scopus 로고
    • Drug-Protein Adducts: An Industry Perspective on Minimizing the Potential for Drug Bioactivation in Drug Discovery and Development
    • DOI 10.1021/tx034170b
    • Evans, D. C.; Watt, A. P.; Nicoll-Griffith, D. A.; Baillie, T. A. Drug-protein adducts: an industry perspective on minimizing the potential for drug bioactivation in drug discovery and development Chem. Res. Toxicol. 2004, 17, 3-16 (Pubitemid 38134055)
    • (2004) Chemical Research in Toxicology , vol.17 , Issue.1 , pp. 3-16
    • Evans, D.C.1    Watt, A.P.2    Nicoll-Griffith, D.A.3    Baillie, T.A.4
  • 29
    • 1642401199 scopus 로고    scopus 로고
    • Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain
    • DOI 10.1038/nature02393
    • Ravelli, R. B.; Gigant, B.; Curmi, P. A.; Jourdain, I.; Lachkar, S.; Sobel, A.; Knossow, M. Insight into tubulin regulation from a complex with colchicines and a stathmin-like domain Nature 2004, 428, 198-202 (Pubitemid 38374318)
    • (2004) Nature , vol.428 , Issue.6979 , pp. 198-202
    • Ravelli, R.B.G.1    Gigant, B.2    Curmi, P.A.3    Jourdain, I.4    Lachkar, S.5    Sobel, A.6    Knossow, M.7
  • 32
    • 70849137218 scopus 로고    scopus 로고
    • Drug interactions in oncology: How common are they?
    • Riechelmann, R. P.; Del Giglio, A. Drug interactions in oncology: how common are they? Ann. Oncol. 2009, 12, 1907-1912
    • (2009) Ann. Oncol. , vol.12 , pp. 1907-1912
    • Riechelmann, R.P.1    Del Giglio, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.