Targeting Epidermal Growth Factor Receptor with Ferrocene-Based Kinase Inhibitors

被引:20
作者
Amin, Jahangir [1 ]
Chuckowree, Irina [1 ]
Tizzard, Graham J. [2 ]
Coles, Simon J. [2 ]
Wang, Minghua [3 ]
Bingham, John P. [4 ]
Hartley, John A. [4 ]
Spencer, John [1 ]
机构
[1] Univ Sussex, Sch Life Sci, Dept Chem, Brighton BN1 9QJ, E Sussex, England
[2] Univ Southampton, Sch Chem, UK Natl Crystallog Serv, Southampton SO17 1BJ, Hants, England
[3] Univ Toronto, Terrence Donnelly Ctr Cellular & Biomol Res, Toronto, ON M5S 3E1, Canada
[4] UCL Canc Inst, CRUK Drug DNA Interact Res Grp, London WC1E 6DD, England
基金
英国工程与自然科学研究理事会;
关键词
ORGANOMETALLIC COMPOUNDS; BIOLOGICAL-ACTIVITY; DRUG; ACTIVATION; REDUCTION; MECHANISM; COMPLEX; PROTEIN; DESIGN;
D O I
10.1021/om300974d
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A series of ferrocene analogues based on a 6,7-dimethoxy-N-phenylquinazolin-4-amine template has been synthesized, and two compounds were characterized in the solid state by X-ray crystallography. The compounds have been tested for in vitro anticancer activity, against epidermal growth receptor (EGFR), and submicromolar IC50 values have been determined.
引用
收藏
页码:509 / 513
页数:5
相关论文
共 34 条
  • [1] [Anonymous], 2008, CRYSTALCLEAR
  • [2] Organometallic compounds with biological activity: A very selective and highly potent cellular inhibitor for glycogen synthase kinase 3
    Atilla-Gokcumen, G. Ekin
    Williams, Douglas S.
    Bregman, Howard
    Pagano, Nicholas
    Meggers, Eric
    [J]. CHEMBIOCHEM, 2006, 7 (09) : 1443 - 1450
  • [3] Synthesis of a biphenyl library for studies of hydrogen bonding in the solid state
    Baltus, Christine B.
    Press, Neil J.
    Antonijevic, Milan D.
    Tizzard, Graham J.
    Coles, Simon J.
    Spencer, John
    [J]. TETRAHEDRON, 2012, 68 (45) : 9272 - 9277
  • [4] Microwave-Mediated Suzuki-Miyaura Cross-Couplings of Thioether- and ortho-Substituted Methylphenylboronic Acid Esters
    Baltus, Christine B.
    Press, Neil J.
    Spencer, John
    [J]. SYNLETT, 2012, (17) : 2477 - 2480
  • [5] Design, synthesis, and biological activity of hybrid compounds between uramustine and DNA minor groove binder distamycin A
    Baraldi, PG
    Romagnoli, R
    Guadix, AE
    de las Infantas, MJP
    Gallo, MA
    Espinosa, A
    Martinez, A
    Bingham, JP
    Hartley, JA
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (17) : 3630 - 3638
  • [6] Bioactive cyclometalated phthalimides: design, synthesis and kinase inhibition
    Blanck, Sebastian
    Geisselbrecht, Yann
    Kraeling, Katja
    Middel, Stephen
    Mietke, Thomas
    Harms, Klaus
    Essen, Lars-Oliver
    Meggers, Eric
    [J]. DALTON TRANSACTIONS, 2012, 41 (31) : 9337 - 9348
  • [7] Bos M, 1997, CLIN CANCER RES, V3, P2099
  • [8] Tyrosine kinase inhibitors .8. An unusually steep structure-activity relationship for analogues of 4-(3-bromoanilino)-6,7-dimethoxyquinazoline (PD 153035), a potent inhibitor of the epidermal growth factor receptor
    Bridges, AJ
    Zhou, H
    Cody, DR
    Rewcastle, GW
    McMichael, A
    Showalter, HDH
    Fry, DW
    Kraker, AJ
    Denny, WA
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (01) : 267 - 276
  • [9] Crystal Structure of the PIM2 Kinase in Complex with an Organoruthenium Inhibitor
    Bullock, Alex N.
    Russo, Santina
    Amos, Ann
    Pagano, Nicholas
    Bregman, Howard
    Debreczeni, Judit E.
    Lee, Wen Hwa
    von Delft, Frank
    Meggers, Eric
    Knapp, Stefan
    [J]. PLOS ONE, 2009, 4 (10):
  • [10] Changing and challenging times for service crystallography
    Coles, Simon J.
    Gale, Philip A.
    [J]. CHEMICAL SCIENCE, 2012, 3 (03) : 683 - 689