Negishi Cross-Coupling Reaction as a Route to Isocombretastatins

被引:8
|
作者
Malysheva, Yulia B. [1 ]
Buchvalova, Svetlana Y. [1 ]
Svirshchevskaya, Elena V. [2 ]
Fokin, Valery V. [3 ]
Fedorov, Alexey Y. [1 ]
机构
[1] Lobachevsky State Univ Nizhni Novgorod, Dept Organ Chem, Nizhnii Novgorod 603950, Russia
[2] Russian Acad Sci, MM Shemyakin & Yu A Ovchinnikov Inst Bioorgan Che, Moscow 117997, Russia
[3] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
基金
俄罗斯基础研究基金会;
关键词
isocombretastatins; antitubulin agents; turbo Grignard reagent; Negishi cross-coupling; cytotoxicity; COMBRETASTATIN A-4 ANALOGS; BIOLOGICAL EVALUATION; 4-ARYLCOUMARIN ANALOGS; ANTINEOPLASTIC AGENTS; SUZUKI-MIYAURA; TUBULIN; MICROTUBULE; HALIDES; 1,1-DIARYLETHYLENES; CHEMISTRY;
D O I
10.1055/s-0033-1339334
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of isocombretastatins A has been synthesized by a new method based on the Negishi cross-coupling reaction in 19-84% yields. Five of the synthesized compounds exhibit high cytotoxic activity in nanomolar concentrations (IC50 = 1-100 nM) towards Jurkat, K562, Colo357, and A549 cell lines.
引用
收藏
页码:1772 / 1776
页数:5
相关论文
共 50 条
  • [1] POxAP Precatalysts and the Negishi Cross-Coupling Reaction
    Tang, Shuang-Qi
    Schmitt, Martine
    Bihel, Frederic J. J.
    SYNTHESIS-STUTTGART, 2020, 52 (01): : 51 - 59
  • [2] An extremely active catalyst for the Negishi cross-coupling reaction
    Milne, JE
    Buchwald, SL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (40) : 13028 - 13032
  • [3] An extremely active catalyst for the Negishi cross-coupling reaction
    Buchwald, S.L. (sbuchwal@mit.edu), 1600, American Chemical Society (126):
  • [4] New insights into the mechanism of the Negishi cross-coupling reaction
    Organ, Michael G.
    Hunter, Howard N.
    Bohme, Diethart K.
    Hadei, Niloufar
    Blagojevic, Voislav
    Achonduh, George T.
    Avola, Stephanie
    McCann, Lucas
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [5] A Negishi cross-coupling reaction enables the total synthesis of (+)-stachyflin
    Haut, Franz-Lucas
    Speck, Klaus
    Wildermuth, Raphael
    Moeller, Kristof
    Mayer, Peter
    Magauer, Thomas
    TETRAHEDRON, 2018, 74 (26) : 3348 - 3357
  • [6] Synthesis of α- and β-Carbolines by a Metalation/Negishi Cross-Coupling/SNAr Reaction Sequence
    Sathiyalingam, Shainthavaan
    Roesner, Stefan
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (10) : 1769 - 1774
  • [7] Synthetic Aromatic Amino Acids from a Negishi Cross-Coupling Reaction
    Suhartono, Marcel
    Schneider, Angelika E.
    Duerner, Gerd
    Goebel, Michael W.
    SYNTHESIS-STUTTGART, 2010, (02): : 293 - 303
  • [8] Online and In Situ Monitoring of the Exchange, Transmetalation, and Cross-Coupling of a Negishi Reaction
    Malig, Thomas C.
    Kumar, Archana
    Kurita, Kenji L.
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2022, 26 (05) : 1514 - 1519
  • [9] New insights into the Negishi cross-coupling reaction: The role of salt additives
    Hoi, Ka Hou
    Calimsiz, Selcuk
    McCann, Lucas
    Organ, Michael
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [10] Recent Developments in Negishi Cross-Coupling Reactions
    Haas, Diana
    Hammann, Jeffrey M.
    Greiner, Robert
    Knochel, Paul
    ACS CATALYSIS, 2016, 6 (03): : 1540 - 1552