Synthesis and Properties of N-Alkyl-6-hydroxy-5-(2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-1H-pyrimidine-2,4-diones and Their 2-Thioanalogs

被引:0
|
作者
K. A. Krasnov
V. G. Kartsev
M. N. Yurova
机构
[1] St. Petersburg Mechnikov State Medical Academy,
[2] ZAO “INTERBIOSKRIN”,undefined
[3] Chernogolovka,undefined
[4] Moscow oblast,undefined
来源
关键词
Spectroscopy; Ethyl; Organic Chemistry; Adduct; Alkaloid;
D O I
暂无
中图分类号
学科分类号
摘要
Addition of N-substituted barbituric and 2-thiobarbituric acids to 3,4-dihydro-β-carboline results in formation of N-alkyl-6-hydroxy-5-(2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-1H-pyrimidine-2,4-diones and their 2-thioanalogs, which are structural analogs of alkaloids from annomontin group. Acylation of 1,3-dimethyl-substituted adduct is accompanied by opening of the tetrahydropyridine ring furnishing N-{2-[2-(1,3-dimethyl-2,4,6-trioxotetrahydropyrimidin-5-ylidenomethyl)-1H-indol-3-yl]ethyl}acetamide. The structure of compounds synthesized was studied by means of 1H NMR spectroscopy.
引用
收藏
页码:596 / 600
页数:4
相关论文
共 50 条
  • [1] Synthesis and properties of N-alkyl-6-hydroxy-5-(2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-1H-pyrimidine-2,4-diones and their 2-thioanalogs
    Krasnov, KA
    Kartsev, VG
    Yurova, MN
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 39 (04) : 596 - 600
  • [2] Diastereomerically directed synthesis of 6-hydroxy-1,3-dimethyl-5-(1R*, 4R*-4-phenyl-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-1H-pyrimidine-2,4-dione
    Semenov, BB
    Novikov, KA
    Krasnov, KA
    Kachala, VV
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2005, (05): : 793 - 795
  • [3] Diastereocontrolled Synthesis of 6-Hydroxy-1,3-dimethyl-5-(R,R-4-phenyl-1,2,3,4-tetrahydro-1H-β-carbolin-1-yl)-1H-pyrimidine-2,4-dione
    B. B. Semenov
    K. A. Novikov
    K. A. Krasnov
    V. V. Kachala
    Chemistry of Heterocyclic Compounds, 2005, 41 (5) : 686 - 688
  • [4] Synthesis of 4-phenyl-1-(2-thienyl)-2,3,4,9-tetrahydro-1H-β-carboline
    B. B. Semenov
    K. A. Novikov
    V. V. Kachala
    V. N. Azev
    Chemistry of Natural Compounds, 2006, 42 : 582 - 584
  • [5] Synthesis of 4-phenyl-1-(2-thienyl)-2,3,4,9-tetrahydro-1H-β-carboline
    Semenov, B. B.
    Novikov, K. A.
    Kachala, V. V.
    Azev, V. N.
    CHEMISTRY OF NATURAL COMPOUNDS, 2006, 42 (05) : 582 - 584
  • [6] Bis(6-methoxy-1-methyl-2,3,4,9-tetrahydro-1H- beta-carbolin-2-ium) tetrachloridozincate(II) dihydrate
    Goh, Teik Beng
    Mordi, Mohd Nizam
    Mansor, Sharif Mahsufi
    Rosli, Mohd Mustaqim
    Fun, Hoong-Kun
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : M464 - +
  • [7] Synthesis of 2-(pyrimidin-2-yl)-1-phenyl-2,3,4,9-tetrahydro-1H-β-carbolines as antileishmanial agents
    Kumar, Ravi
    Khan, Shahnawaz
    Verma, Aditya
    Srivastava, Saumya
    Viswakarma, Preeti
    Gupta, Suman
    Meena, Sanjeev
    Singh, Neetu
    Sarkar, Jayanta
    Chauhan, Prem M. S.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (08) : 3274 - 3280
  • [8] Synthesis of 5-acyl-6-[2-hydroxy-3-(amino)propylamino-]1,3-dialkyl-1H-pyrimidine-2,4-diones
    Singh, P
    Paul, K
    Holzer, W
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (21) : 3958 - 3965
  • [9] Synthesis of Novel Tetrazole Containing Quinoline and 2,3,4,9-Tetrahydro-1H-β-Carboline Derivatives
    Ghandi, Mehdi
    Rahimi, Shahnaz
    Zarezadeh, Nahid
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (01) : 102 - 109
  • [10] 9-(2-Hydroxy-6-oxocyclohex-1-en-1-yl)-2,3,4,9-tetrahydro-1H-xanthen-1-one
    Mohamed, Shaaban K.
    Akkurt, Mehmet
    Abdelhamid, Antar A.
    Saeed, Aamer
    Florke, Ulrich
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O616 - +