Heterocycles as classical and nonclassical ring B isosters in combretastatin A-4

被引:8
作者
Zefirov, Nikolay A. [1 ]
Zefirova, Olga N. [1 ,2 ]
机构
[1] Lomonosov Moscow State Univ, Dept Chem, Leninskie Gory 1-3, Moscow 119991, Russia
[2] Inst Physiol Act Cpds, Severny Proezd 1, Chernogolovka 142432, Moscow Region, Russia
基金
俄罗斯基础研究基金会;
关键词
combretastatin A-4; cytotoxicity; heterocycles; isosteric replacement; structure-activity relationship; TUBULIN POLYMERIZATION INHIBITORS; COLCHICINE BINDING-SITE; BIOLOGICAL EVALUATION; ANTICANCER AGENTS; COMMON PHARMACOPHORE; CYTOTOXIC ACTIVITIES; ANTIMITOTIC AGENTS; DRUG DESIGN; ANALOGS; DERIVATIVES;
D O I
10.1007/s10593-017-2049-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The minireview provides a survey of combretastatin A-4 analogs, obtained by isosteric replacement of 3-hydroxy-4-methoxyphenyl ring (ring B) with various heterocyclic systems. The basic synthetic approaches and structure-activity relationships are summarized.
引用
收藏
页码:273 / 280
页数:8
相关论文
共 47 条
  • [1] Synthesis and biotests of 2-aryl-5-arylmethylidene-substituted 1,3-oxazol-5(4H)-ones and N-methyl-3,5-dihydro-4H-imidazol-4-ones as combretastatin A-4 analogs
    Barskaia, E. S.
    Beloglazkina, A. A.
    Wobith, B.
    Zefirov, N. A.
    Majouga, A. G.
    Beloglazkina, E. K.
    Zyk, N. V.
    Kuznetsov, S. A.
    Zefirova, O. N.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2015, 64 (07) : 1560 - 1563
  • [2] An Efficient Microwave-Promoted Route to (Z)-Stilbenes from trans-Cinnamic Acids: Synthesis of Combretastatin A-4 and Analogues
    Bazin, Marc-Antoine
    Jouanne, Marie
    El-Kashef, Hussein
    Rault, Sylvain
    [J]. SYNLETT, 2009, (17) : 2789 - 2794
  • [3] Synthesis and biological testing of (5Z)-2-aryl-5-arylmethylidene-3,5-dihydro-4H-imidazol-4-ones as antimitotic agents
    Beloglazkina, Anastasia A.
    Wobith, Birgit
    Barskaia, Elena S.
    Zefirov, Nikolay A.
    Majouga, Alexander G.
    Beloglazkina, Elena K.
    Zyk, Nikolay V.
    Kuznetsov, Sergei A.
    Zefirova, Olga N.
    [J]. MEDICINAL CHEMISTRY RESEARCH, 2016, 25 (06) : 1239 - 1249
  • [4] Sydnone Cycloaddition Route to Pyrazole-Based Analogs of Combretastatin A4
    Brown, Andrew W.
    Fisher, Matthew
    Tozer, Gillian M.
    Kanthou, Chryso
    Harrity, Joseph P. A.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (20) : 9473 - 9488
  • [5] Novel Combretastatin-2-aminoimidazole Analogues as Potent Tubulin Assembly Inhibitors: Exploration of Unique Pharmacophoric Impact of Bridging Skeleton and Aryl Moiety
    Chaudhary, Vikas
    Venghateri, Jubina B.
    Dhaked, Hemendra P. S.
    Bhoyar, Anil S.
    Guchhait, Sankar K.
    Panda, Dulal
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (07) : 3439 - 3451
  • [6] Synthesis and biological evaluation of thiophene and benzo[b]thiophene analogs of combretastatin A-4 and isocombretastatin A-4: A comparison between the linkage positions of the 3,4,5-trimethoxystyrene unit
    Cong Viet Do
    Faouzi, Abdelfattah
    Barette, Caroline
    Farce, Amaury
    Fauvarque, Marie-Odile
    Colomb, Evelyne
    Catry, Laura
    Berthier-Vergnes, Odile
    Haftek, Marek
    Barret, Roland
    Lomberget, Thierry
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (01) : 174 - 180
  • [7] SYNTHESIS AND EVALUATION OF STILBENE AND DIHYDROSTILBENE DERIVATIVES AS POTENTIAL ANTICANCER AGENTS THAT INHIBIT TUBULIN POLYMERIZATION
    CUSHMAN, M
    NAGARATHNAM, D
    GOPAL, D
    CHAKRABORTI, AK
    LIN, CM
    HAMEL, E
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (08) : 2579 - 2588
  • [8] Combretastatin A-4 analogues with benzoxazolone scaffold: Synthesis, structure and biological activity
    Gerova, Mariana S.
    Stateva, Silviya R.
    Radonova, Elena M.
    Kalenderska, Rositsa B.
    Rusew, Rusi I.
    Nikolova, Rositsa P.
    Chanev, Christo D.
    Shivachev, Boris L.
    Apostolova, Margarita D.
    Petrov, Ognyan I.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 120 : 121 - 133
  • [9] González MA, 2012, NAT PROD COMMUN, V7, P1051
  • [10] Novel B-ring modified combretastatin analogues: Syntheses and antineoplastic activity
    Hatanaka, T
    Fujita, K
    Ohsumi, K
    Nakagawa, R
    Fukuda, Y
    Nihei, Y
    Suga, Y
    Akiyama, Y
    Tsuji, T
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (23) : 3371 - 3374