Synthesis of Three Stereoisomers of p-tert-Butylthiacalix[4] arene Substituted with (Ethoxycarbonyl) methoxy and Fluorescent 1-Amidoanthraquinone Fragments

被引:10
作者
Vavilova, Alena A. [1 ]
Nosov, Roman V. [1 ]
Mostovaya, Olga A. [1 ]
Stoikov, Ivan I. [1 ]
机构
[1] Kazan Fed Univ, AM Butlerov Chem Inst, Kazan 420008, Russia
来源
MACROHETEROCYCLES | 2016年 / 9卷 / 03期
基金
俄罗斯科学基金会;
关键词
Thiacalix[4] arene; synthesis; template effect; fluorescence spectroscopy; P-TERT-BUTYL; LOWER RIM; DERIVATIVES; THIACALIXARENES; BINDING;
D O I
10.6060/mhc160531s
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
New tetrasubstituted at the lower rim thiacalix[4]arenes containing both (ethoxycarbonyl) methoxy and 1-amidoanthraquinone fragments in three conformations: cone, partial cone and 1,3-alternate were synthesized. It was shown that depending on the alkali metal cation (sodium, potassium or cesium) in the alkylation of the diester based on p-tert-butylthiacalix[4] arene by 2-bromo-N-(9', 10'-dioxo-9', 10'-dihydroanthracene-1'-yl) acetamide template effect of metal cation was observed. The fluorescent properties of the obtained compounds were studied.
引用
收藏
页码:294 / 300
页数:7
相关论文
共 25 条
  • [1] Fluorescent Probes and Fluorescence (Microscopy) Techniques - Illuminating Biological and Biomedical Research
    Drummen, Gregor P. C.
    [J]. MOLECULES, 2012, 17 (12) : 14067 - 14090
  • [2] ESIPT-based anthraquinonylcalix[4]crown chemosensor for In3+
    Han, Do Young
    Kim, Jun Myung
    Kim, Joohoon
    Jung, Hyo Sung
    Lee, Young Hoon
    Zhang, Jun Feng
    Kim, Jong Seung
    [J]. TETRAHEDRON LETTERS, 2010, 51 (15) : 1947 - 1951
  • [3] Near-infrared fluorescence: application to in vivo molecular imaging
    Hilderbrand, Scott A.
    Weissleder, Ralph
    [J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 2010, 14 (01) : 71 - 79
  • [4] Novel molecular receptors based on a thiacalix[4]arene platform. Preparations of the di- and tetracarboxylic acid derivatives and their binding properties towards transition metal ions
    Iki, N
    Morohashi, N
    Narumi, F
    Fujimoto, T
    Suzuki, T
    Miyano, S
    [J]. TETRAHEDRON LETTERS, 1999, 40 (41) : 7337 - 7341
  • [5] A new fluorescent chemosensor for F- based on inhibition of excited-state intramolecular proton transfer
    Jung, Hyci Sung
    Kim, Hyun Jung
    Vicens, Jacques
    Kim, Jong Seung
    [J]. TETRAHEDRON LETTERS, 2009, 50 (09) : 983 - 987
  • [6] New Strategies for Fluorescent Probe Design in Medical Diagnostic Imaging
    Kobayashi, Hisataka
    Ogawa, Mikako
    Alford, Raphael
    Choyke, Peter L.
    Urano, Yasuteru
    [J]. CHEMICAL REVIEWS, 2010, 110 (05) : 2620 - 2640
  • [7] Lakowicz J. R., 2006, Principles of fluorescence spectroscopy, DOI [DOI 10.1007/978-0-387-46312-4, DOI 10.1007/978-0-387-46312-4/COVER]
  • [8] Chemistry of thiacalixarenes
    Lhoták, P
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (08) : 1675 - 1692
  • [9] Thiacalixarenes
    Morohashi, Naoya
    Narumi, Fumitaka
    Iki, Nobuhiko
    Hattori, Tetsutaro
    Miyano, Sotaro
    [J]. CHEMICAL REVIEWS, 2006, 106 (12) : 5291 - 5316
  • [10] DEVELOPMENT OF LUMINESCENCE SPECTROMETRY AS AN ANALYTICAL TOOL
    OHAVER, TC
    [J]. JOURNAL OF CHEMICAL EDUCATION, 1978, 55 (07) : 423 - 428