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
  • [21] The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4
    Flynn, BL
    Flynn, GP
    Hamel, E
    Jung, MK
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (17) : 2341 - 2343
  • [22] Design, stereoselective synthesis, and antitumoral activity of combretastatin A-4 analogs
    da Silva, Wilson P.
    Caiana, Robrigo R. A.
    Barros, Maria E. S. B.
    Freitas, Juliano C. R.
    da Silva, Paulo B. N.
    Milita, Gardenia G. C.
    Oliveira, Roberta A.
    Menezes, Paulo H.
    RESULTS IN CHEMISTRY, 2024, 7
  • [23] Photoswitching off the Antiproliferative Activity of Combretastatin A-4 Analogues
    Yadykov, Anton V.
    Scherbakov, Alexander M.
    Trofimova, Victoria V.
    Lvov, Andrey G.
    Markosyan, Ashot I.
    Zavarzin, Igor V.
    Shirinian, Valerii Z.
    ORGANIC LETTERS, 2019, 21 (23) : 9608 - 9612
  • [24] Synthesis and cytotoxic activity of novel water-soluble prodrugs of combretastatin A-4
    Yong, ZQ
    Xu, XP
    Chen, YC
    Bao, X
    Weng, LL
    Zheng, H
    CHINESE CHEMICAL LETTERS, 2006, 17 (01) : 23 - 26
  • [25] Synthesis of New Combretastatin A-4 Analogues and Study of Their Anti-Inflammatory Activity
    Davydova, M. P.
    Sorokina, I. V.
    Tolstikova, T. G.
    Mamatyuk, V. I.
    Fadeev, D. S.
    Vasilevsky, S. F.
    RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2015, 41 (01) : 70 - 76
  • [26] Synthesis of new combretastatin A-4 analogues and study of their anti-inflammatory activity
    M. P. Davydova
    I. V. Sorokina
    T. G. Tolstikova
    V. I. Mamatyuk
    D. S. Fadeev
    S. F. Vasilevsky
    Russian Journal of Bioorganic Chemistry, 2015, 41 : 70 - 76
  • [27] Photostability and Antiproliferative Activity of Furan Analogues of Combretastatin A-4
    Scherbakov, Alexander
    Zakharov, Alexey V.
    Mikhaevich, Ekaterina I.
    Salnikova, Diana I.
    Yadykov, Anton V.
    Kozhevnikova, Arina A.
    Shirinian, Valerii Z.
    CHEMICAL RESEARCH IN TOXICOLOGY, 2022, 35 (11) : 2014 - 2024
  • [28] Synthesis of dihydronaphthalene analogues inspired by combretastatin A-4 and their biological evaluation as anticancer agents
    Maguire, Casey J.
    Chen, Zhi
    Mocharla, Vani P.
    Sriram, Madhavi
    Strecker, Tracy E.
    Hamel, Ernest
    Zhou, Heling
    Lopez, Ramona
    Wang, Yifan
    Mason, Ralph P.
    Chaplin, David J.
    Trawick, Mary Lynn
    Pinney, Kevin G.
    MEDCHEMCOMM, 2018, 9 (10) : 1649 - 1662
  • [30] Cytotoxic activities and metabolic studies of new combretastatin analogues
    Yohan Macé
    Emilie Bony
    David Delvaux
    Adan Pinto
    Véronique Mathieu
    Robert Kiss
    Olivier Feron
    Joëlle Quetin-Leclercq
    Olivier Riant
    Medicinal Chemistry Research, 2015, 24 : 3143 - 3156