Synthesis and Biological Activity of Estafiatin Phosphonate Derivatives

被引:6
|
作者
Suleimen, E. M. [1 ]
Dzhalmakhanbetova, R. I. [1 ]
Pak, R. N. [2 ]
Kulyyasov, A. T. [2 ]
Adekenov, S. M. [2 ]
机构
[1] Eurasian Natl Univ, LN Gumilev Inst Appl Chem, Astana 010008, Kazakhstan
[2] Phytochem Corp, Karaganda 100019, Kazakhstan
关键词
sesquiterpene lactones; chemical modification; phosphorus-derivatives; two-dimensional spectra; antimicrobial activity;
D O I
10.1007/s10600-014-1097-3
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Four new dialkylphosphonate derivatives 2-5 were prepared for the first time from the guaiane-type sesquiterpene lactone estafiatin (1), which was isolated from the aerial part of Achillea nobilis. Their structures were elucidated using PMR, C-13 NMR, two-dimensional H-1-H-1 COSY, C-13-H-1 COLOC, and P-31-H-1 spectroscopy. The estafiatin phosphorylation reaction was highly chemo- and stereoselective. The antimicrobial activity of the prepared derivatives was studied.
引用
收藏
页码:846 / 849
页数:4
相关论文
共 50 条
  • [1] Synthesis and Biological Activity of Estafiatin Phosphonate Derivatives
    E. M. Suleimen
    R. I. Dzhalmakhanbetova
    R. N. Pak
    A. T. Kulyyasov
    S. M. Adekenov
    Chemistry of Natural Compounds, 2014, 50 : 846 - 849
  • [2] Synthesis and biological activity of nitrogen-containing derivatives of estafiatin
    Merkhatuly, N.
    Vojtisek, P.
    Abeuova, S. B.
    Omarova, A. T.
    Iskanderov, A. N.
    BULLETIN OF THE UNIVERSITY OF KARAGANDA-CHEMISTRY, 2014, (74): : 4 - 8
  • [3] Synthesis of dihalocarbene derivatives of estafiatin guaianolide
    R. I. Jalmakhanbetova
    V. A. Raldugin
    I. Yu. Bagryanskaya
    Yu. V. Gatilov
    M. M. Shakirov
    G. A. Atazhanova
    S. M. Adekenov
    Chemistry of Natural Compounds, 2007, 43 : 552 - 554
  • [4] Synthesis of dihalocarbene derivatives of estafiatin guaianolide
    Jalmakhanbetova, R. I.
    Raldugin, V. A.
    Bagryanskaya, I. Yu.
    Gatilov, Yu. V.
    Shakirov, M. M.
    Atazhanova, G. A.
    Adekenov, S. M.
    CHEMISTRY OF NATURAL COMPOUNDS, 2007, 43 (05) : 552 - 554
  • [5] SYNTHESIS AND BIOLOGICAL ACTIVITY OF BORANE PHOSPHONATE DNA
    Olesiak, Magdalena
    Krivenko, Angelika
    Krishna, Heera
    Caruthers, Marvin H.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2011, 186 (04) : 921 - 932
  • [6] Synthesis and biological evaluation of phosphonate derivatives as autotaxin (ATX) inhibitors
    Cui, Peng
    Tomsig, Jose L.
    McCalmont, William F.
    Lee, Sangderk
    Becker, Christopher J.
    Lynch, Kevin R.
    Macdonald, Timothy L.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (06) : 1634 - 1640
  • [7] Synthesis, Characterization and Antitumor Activity of Benzimidazole Phosphonate Derivatives
    Sabry, Eman
    Abu Bakr, Sherifa M.
    Khidre, Maha D.
    Awad, Hanem M.
    Sediek, Ashraf A.
    EGYPTIAN JOURNAL OF CHEMISTRY, 2024, 67 (13): : 443 - 452
  • [8] Synthesis and Antibacterial Activity of Novel Phosphonate Derivatives Containing Flavonoids
    Huang, Minguo
    Ruan, Xianghui
    Zhang, Juping
    Li, Qin
    Wang, Yihui
    Chen, Lijuan
    Zhang, Cheng
    Li, Pu
    Xue, Wei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (08) : 2145 - 2152
  • [9] Synthesis and Antibacterial Activity of Sulfanilamide Derivatives Containing Phosphonate Moiety
    Yang, Jia-Qiang
    Deng, Ling
    An, Jia-Li
    Zhao, Shi-Xin
    Jingxi Huagong/Fine Chemicals, 2019, 36 (09): : 1869 - 1873
  • [10] Synthesis and biological activity of novel phosphonate derivatives containing of pyridyl and 1,2,3-triazole rings
    Chen, Xiao-Bao
    Shi, De-Qing
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (05) : 1134 - 1144