Synthesis of thiourea derivatives of the alkaloid anabasine and crystal structure of N-(anabasino-1-thiocarbonyl)furan-2-carboxamide

被引:15
|
作者
Kulakov, I. V. [1 ]
Nurkenov, O. A. [1 ]
Turdybekov, D. M. [2 ]
Ibragimov, B. T. [3 ]
Talipov, S. A. [3 ]
Zhambekov, Z. M. [1 ]
Ainabaev, A. A. [1 ]
Turdybekov, K. M. [2 ]
机构
[1] Inst Organ Synth & Carbon Chem Republ Kazakhstan, Karaganda 100008, Kazakhstan
[2] Sci Prod Ctr Fitokhimiya, Karaganda 100009, Kazakhstan
[3] Inst Bioorgan Chem, Tashkent 100125, Uzbekistan
关键词
alkaloid anabasine; thiourea derivatives; isothiocyanates; PMR spectroscopy; x-ray structure analysis; antibacterial activity;
D O I
10.1007/s10600-009-9284-3
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of new N-acylsubstituted thioureas, the compositions and structures of which were determined by IR and PMR spectroscopy and mass spectrometry, were synthesized from the alkaloid anabasine. The crystal structure of one of the products, N-(anabasino-1-thiocarbonyl)furan-2-carboxamide, was confirmed by x-ray structure analysis. It was also shown that this compound exhibited moderate antibacterial activity.
引用
收藏
页码:209 / 212
页数:4
相关论文
共 50 条
  • [1] Synthesis of thiourea derivatives of the alkaloid anabasine and crystal structure of N-(anabasino1-thiocarbonyl)furan-2-carboxamide
    I. V. Kulakov
    O. A. Nurkenov
    D. M. Turdybekov
    B. T. Ibragimov
    S. A. Talipov
    Z. M. Zhambekov
    A. A. Ainabaev
    K. M. Turdybekov
    Chemistry of Natural Compounds, 2009, 45 : 209 - 212
  • [2] N-(2-Nitrophenyl)furan-2-carboxamide
    Moreno-Fuquen, Rodolfo
    Azcarate, Alexis
    Kennedy, Alan R.
    Gilmour, Denise
    De Almeida Santos, Regina H.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O1592 - +
  • [3] Synthesis, Characterization, and Antimicrobial Evaluation of New Furan-2-Carboxamide Derivatives
    Sweidan, Kamal
    Idrees, Gada
    Abu-Qatouseh, Luay
    Tahir, Muhammad Nawaz
    Khanfar, Monther
    Joshi, Rajendra
    Mallah, Eyad
    Mubarak, Mohammsad S.
    LETTERS IN ORGANIC CHEMISTRY, 2022, 19 (04) : 314 - 325
  • [4] Synthesis, characterization, crystal structure, hirshfeld surface analysis and DFT calculations of N-(pyridin-2-ylmethyl)furan-2-carboxamide and its molecular docking
    M. Mohanbabu
    P. N. Sathishkumar
    N. S. P. Bhuvanesh
    R. Karvembu
    K. Saravanan
    E. Vinoth
    S. Aravindhan
    Journal of Materials Science: Materials in Electronics, 2022, 33 : 9616 - 9628
  • [5] Synthesis, characterization, crystal structure, hirshfeld surface analysis and DFT calculations of N-(pyridin-2-ylmethyl)furan-2-carboxamide and its molecular docking
    Mohanbabu, M.
    Sathishkumar, P. N.
    Bhuvanesh, N. S. P.
    Karvembu, R.
    Saravanan, K.
    Vinoth, E.
    Aravindhan, S.
    JOURNAL OF MATERIALS SCIENCE-MATERIALS IN ELECTRONICS, 2022, 33 (12) : 9616 - 9628
  • [6] New N-(1,3,4-thiadiazol-2-yl)furan-2-carboxamide derivatives as potential inhibitors of the VEGFR-2
    Hekal, Mohamed H.
    Farag, Paula S.
    Hemdan, Magdy M.
    El-Sayed, Wael M.
    BIOORGANIC CHEMISTRY, 2021, 115
  • [7] (E)-N-[2-(Biphenyl-4-ylvinyl)phenyl]furan-2-carboxamide
    Kee, Chin Hui
    Thomas, Noel F.
    Ariffin, Azhar
    Awang, Khalijah
    Ng, Seik Weng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O2210 - U2833
  • [8] Structures and properties in different media of N,N-(diethylcarbamothioyl)furan-2-carboxamide: A ionophore for sensor membranes
    Lazo Fraga, Ana Rosa
    Collins, Anna
    Forte, Giuseppe
    Rescifina, Antonio
    Punzo, Francesco
    JOURNAL OF MOLECULAR STRUCTURE, 2009, 929 (1-3) : 174 - 181
  • [9] Synthesis, characterization and corrosion inhibition efficiency of N-(4-(Morpholinomethyl Carbamoyl Phenyl) Furan-2-Carboxamide for brass in HCl medium
    Zulfareen, N.
    Kannan, K.
    Venugopal, T.
    Gnanavel, S.
    ARABIAN JOURNAL OF CHEMISTRY, 2016, 9 (01) : 121 - 135
  • [10] Synthesis of Thiourea Derivatives of the Alkaloids Anabasine, Cytisine, and d-Pseudoephedrine. Crystal Structure of N-ethyl-N-Anabasinocarbothioamide
    O. A. Nurkenov
    Zh. B. Satpaeva
    S. D. Fazylov
    T. M. Seilkhanov
    K. M. Turdybekov
    D. M. Turdybekov
    S. B. Akhmetova
    A. S. Makhmutova
    A. M. Gazaliev
    Chemistry of Natural Compounds, 2016, 52 : 276 - 279