Synthesis of Functionalized Difluorocyclopropanes: Unique Building Blocks for Drug Discovery

被引：44
作者：
Bychek, Roman M. [1 ]
Levterov, Vadym V. [1 ]
Sadkova, Iryna V. [1 ]
Tolmachev, Andrey A. [1 ,2 ]
Mykhailiuk, Pavel K. [1 ,2 ]
机构：
[1] Enamine Ltd, Chervonotkatska 78, UA-02094 Kiev, Ukraine
[2] Taras Shevchenko Natl Univ Kyiv, Dept Chem, Volodymyrska 64, UA-01601 Kiev, Ukraine
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 47期
关键词：
amines; cycloaddition; drug discovery; difluorocyclopropane; fluorine; GEM-DIFLUORINATED CYCLOPROPANES; MEDICINAL CHEMISTRY; F-19; NMR; ESCHERICHIA-COLI; MEMBRANE-PROTEIN; FLUORINE; DIFLUOROCARBENE; PROLINE; PEPTIDE; CONFORMATION;
D O I：
10.1002/chem.201705708
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Difluorocyclopropane-containing building blocks for drug discovery were synthesized from the functionalized alkenes and TMSCF3/NaI. Novel fluorinated acids, amines, amino acids, alcohols, ketones and sulfonyl chlorides were obtained.
引用
收藏
页码：12291 / 12297
页数：7
相关论文
共 58 条
  • [1] [Anonymous], 2004, ChemBioChem, V5, P557
  • [2] Synthesis of Trifluoromethyl-Substituted 3-Azabicyclo[n.1.0]alkanes: Advanced Building Blocks for Drug Discovery
    Artamonov, Olexiy S.
    Slobodyanyuk, Evgeniy Y.
    Volochnyuk, Dmitriy M.
    Komarov, Igor V.
    Tolmachev, Andrey A.
    Mykhailiuk, Pavel K.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (17) : 3592 - 3598
  • [3] Synthesis of Isomeric 6-Trifluoromethyl-3-azabicyclo[3.1.0]hexanes: Conformationally Restricted Analogues of 4-Trifluoromethylpiperidine
    Artamonov, Olexiy S.
    Slobodyanyuk, Evgeniy Y.
    Shishkin, Oleg V.
    Komarov, Igor V.
    Mykhailiuk, Pavel K.
    [J]. SYNTHESIS-STUTTGART, 2013, 45 (02): : 225 - 230
  • [4] Baudoux J., 2008, ELECTROPHILIC FLUORI, P347
  • [5] (5S)-5-(Trifluoromethyl)pyrrolidin-2-one as a Promising Building Block for Fluoroorganic Chemistry
    Bezdudny, Andrii V.
    Alekseenko, Anatoliy N.
    Mykhailiuk, Pavel K.
    Manoilenko, Olga V.
    Shishkin, Oleg V.
    Pustovit, Yurii M.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (09) : 1782 - 1785
  • [6] Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine
  • [7] Sulfonyl Fluorides as Alternative to Sulfonyl Chlorides in Parallel Synthesis of Aliphatic Sulfonamides
    Bogolubsky, Andrey V.
    Moroz, Yurii S.
    Mykhailiuk, Pavel K.
    Pipko, Sergey E.
    Konovets, Anzhelika I.
    Sadkova, Irina V.
    Tolmachev, Andrey
    [J]. ACS COMBINATORIAL SCIENCE, 2014, 16 (04) : 192 - 197
  • [8] Fluorine in medicinal chemistry
    Böhm, HJ
    Banner, D
    Bendels, S
    Kansy, M
    Kuhn, B
    Müller, K
    Obst-Sander, U
    Stahl, M
    [J]. CHEMBIOCHEM, 2004, 5 (05) : 637 - 643
  • [9] Fluorinated carbenes
    Brahms, DLS
    Dailey, WP
    [J]. CHEMICAL REVIEWS, 1996, 96 (05) : 1585 - 1632
  • [10] Iodocyclization of Chiral CF3-Allylmorpholinones: A Versatile Strategy for the Synthesis of Enantiopure α-Tfm-Prolines and α-Tfm-Dihydroxyprolines
    Caupene, Caroline
    Chaume, Gregory
    Ricard, Louis
    Brigaud, Thierry
    [J]. ORGANIC LETTERS, 2009, 11 (01) : 209 - 212
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