Design, synthesis and cytotoxic activities of naphthyl analogues of combretastatin A-4

被引:41
|
作者
Maya, ABS
del Rey, B
de Clairac, RPL
Caballero, E
Barasoain, I
Andreu, JM
Medarde, M
机构
[1] Univ Salamanca, Fac Farm, Lab Quim Organ & Farmaceut, E-37007 Salamanca, Spain
[2] CSIC, Ctr Invest Biol, E-28006 Madrid, Spain
关键词
D O I
10.1016/S0960-894X(00)00506-0
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The 3,4,5-trimethoxyphenyl and 3-hydroxy-4-methoxyphenyl rings of combretastatin A-4 are deemed optimal for its activity as antimitotic agent. The replacement of either one by a naphthalene ring results in compounds with a potency comparable to that of the parent compound. These results show that the naphthalene ring is a good surrogate for the 3,4,5-trimethoxyphenyl or the 3-hydroxy-4-methoxyphenyl rings of combretastatin A-4 and that neither of them is essential for the antitumor activity. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2549 / 2551
页数:3
相关论文
共 50 条
  • [41] Novel sulfonate analogues of combretastatin A-4: Potent antimitotic agents
    Gwaltney, SL
    Imade, HM
    Barr, KJ
    Li, Q
    Gehrke, L
    Credo, RB
    Warner, RB
    Lee, JY
    Kovar, P
    Wang, JY
    Nukkala, MA
    Zielinski, NA
    Frost, D
    Ng, SC
    Sham, HL
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (07) : 871 - 874
  • [42] Synthesis,characterization and biological activities of nitrogen-containing Combretastatin A-4 derivatives
    Hui Tang
    Yunli Liu
    Hui Nie
    Kangyan Xue
    Jinwen Huang
    Fanhong Wu
    Medicinal Chemistry Research, 2022, 31 : 2160 - 2171
  • [43] Combretastatin A-4: The Antitubulin Agent that Inspired the Design and Synthesis of Styrene and Spiroisatin Hybrids as Promising Cytotoxic, Antifungal and Antiviral Compounds
    Brand, Yaneth M.
    Kouznetsov, Vladimir V.
    Puerto, Carlos E.
    Linares, Vicky C. R.
    Castano, Veronica T.
    Betancur-Galvis, Liliana
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2020, 31 (05) : 999 - 1010
  • [44] Synthesis of Diaryl Pyrrolones Derivatives as Combretastatin A-4
    Wei, Li
    Lu, Guo-Yuan
    ADVANCES IN MATERIALS AND MATERIALS PROCESSING, PTS 1-3, 2013, 652-654 : 689 - 692
  • [45] Synthesis of combretastatin A-4 O-alkyl derivatives and evaluation of their cytotoxic, antiangiogenic and antitelomerase activity
    Torijano-Gutierrez, Sandra
    Diaz-Oltra, Santiago
    Falomir, Eva
    Murga, Juan
    Carda, Miguel
    Marco, J. Alberto
    BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (23) : 7267 - 7274
  • [46] Tandem Heck-Suzuki-Miyaura reaction: Application to the synthesis of constrained analogues of combretastatin A-4
    Arthuis, Martin
    Pontikis, Renee
    Florent, Jean-Claude
    TETRAHEDRON LETTERS, 2007, 48 (36) : 6397 - 6400
  • [47] Design and synthesis of novel enhanced water soluble hydroxyethyl analogs of combretastatin A-4
    Lee, Megan
    Brockway, Olivia
    Dandavati, Armaan
    Tzou, Samuel
    Sjoholm, Robert
    Nickols, Alexis
    Babu, Balaji
    Chavda, Sameer
    Satam, Vijay
    Hartley, Rachel M.
    Westbrook, Cara
    Mooberry, Susan L.
    Fraley, Gregory
    Lee, Moses
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (07) : 2087 - 2091
  • [48] Design and synthesis of combretastatin analogues.
    Gaukroger, K
    Hadfield, JA
    Lawrence, NJ
    McGown, AT
    CLINICAL CANCER RESEARCH, 2000, 6 : 4531S - 4531S
  • [49] Design and synthesis of novel combretastatin analogues
    Gaukroger, K
    Hadfield, JA
    Lawrence, NJ
    McGown, AT
    BRITISH JOURNAL OF CANCER, 2000, 83 : 30 - 30
  • [50] Design, synthesis, biological evaluation and cocrystal structures with tubulin of chiral β-lactam bridged combretastatin A-4 analogues as potent antitumor agents
    Zhou, Pengfei
    Liang, Yuru
    Zhang, Hao
    Jiang, Hao
    Feng, Kechang
    Xu, Pan
    Wang, Jie
    Wang, Xiaoming
    Ding, Kuiling
    Luo, Cheng
    Liu, Mingming
    Wang, Yang
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 144 : 817 - 842