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
  • [31] Synthesis and cytotoxic activity of certain trisubstituted azetidin-2-one derivatives as a cis-restricted combretastatin A-4 analogues
    Elmeligie, Salwa
    Taher, Azza. T.
    Khalil, Nadia A.
    El-said, Ahmed H.
    ARCHIVES OF PHARMACAL RESEARCH, 2017, 40 (01) : 13 - 24
  • [32] Cytotoxic activities and metabolic studies of new combretastatin analogues
    Mace, Yohan
    Bony, Emilie
    Delvaux, David
    Pinto, Adan
    Mathieu, Veronique
    Kiss, Robert
    Feron, Olivier
    Quetin-Leclercq, Joelle
    Riant, Olivier
    MEDICINAL CHEMISTRY RESEARCH, 2015, 24 (08) : 3143 - 3156
  • [33] Potent Quinoline-Containing Combretastatin A-4 Analogues: Design, Synthesis, Antiproliferative, and Anti-Tubulin Activity
    Ibrahim, Tarek S.
    Hawwas, Mohamed M.
    Malebari, Azizah M.
    Taher, Ehab S.
    Omar, Abdelsattar M.
    O'Boyle, Niamh M.
    McLoughlin, Eavan
    Abdel-Samii, Zakaria K.
    Elshaier, Yaseen A. M. M.
    PHARMACEUTICALS, 2020, 13 (11) : 1 - 22
  • [34] Synthesis and cytotoxic activity of certain trisubstituted azetidin-2-one derivatives as a cis-restricted combretastatin A-4 analogues
    Salwa Elmeligie
    Azza. T. Taher
    Nadia A. Khalil
    Ahmed H. El-said
    Archives of Pharmacal Research, 2017, 40 : 13 - 24
  • [35] Design, concise synthesis and evaluation of novel amide-based combretastatin A-4 analogues as potent tubulin inhibitors
    Ma, Yufeng
    Wang, Ting
    Cheng, Li
    Ma, Xuanxuan
    Li, Rou
    Zhang, Mengting
    Chen, Jingkao
    Zhao, Peiliang
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2024, 108
  • [36] Synthesis and cytotoxic evaluation of cis-locked and constrained analogues of combretastatin and combretastatin A4
    Lorion, Magali
    Agouridas, Vangelis
    Couture, Axel
    Deniau, Eric
    Grandclaudon, Pierre
    TETRAHEDRON LETTERS, 2010, 51 (39) : 5146 - 5149
  • [37] Synthesis and Biological Evaluation of New cis-Restricted Triazole Analogues of Combretastatin A-4
    Prieto, Lidia
    Gavina, Daniel
    Escolano, Marcos
    Canovas-Belchi, Maria
    Sanchez-Rosello, Maria
    del Pozo, Carlos
    Falomir, Eva
    Diaz-Oltra, Santiago
    MOLECULES, 2025, 30 (02):
  • [38] Synthesis and Biological Evaluations of 1,2-Diaryl Pyrroles as Analogues of Combretastatin A-4
    Sun, Jun
    Chen, Lei
    Liu, Chunjiang
    Wang, Zhan
    Zuo, Daiying
    Pan, Jiatong
    Qi, Huan
    Bao, Kai
    Wu, Yingliang
    Zhang, Weige
    CHEMICAL BIOLOGY & DRUG DESIGN, 2015, 86 (06) : 1541 - 1547
  • [39] Synthesis,characterization and biological activities of nitrogen-containing Combretastatin A-4 derivatives
    Tang, Hui
    Liu, Yunli
    Nie, Hui
    Xue, Kangyan
    Huang, Jinwen
    Wu, Fanhong
    MEDICINAL CHEMISTRY RESEARCH, 2022, 31 (12) : 2160 - 2171
  • [40] Design, Synthesis and Biological Evaluation of Novel Aminosaccharide Derivatives of Combretastatin A-4
    Tang, Yan
    Tu, Zhewei
    Sun, Jing
    Zhu, Xiong
    Liu, Kun
    He, Shuying
    Xu, Yungen
    LETTERS IN DRUG DESIGN & DISCOVERY, 2013, 10 (10) : 935 - 941