Ionic liquid catalyzed one-pot multi-component synthesis, characterization and antibacterial activity of novel chromeno[2,3-d]pyrimidin-8-amine derivatives

被引:38
作者
Kanakaraju, Sankari [1 ]
Prasanna, Bethanamudi [1 ]
Basavoju, Srinivas [1 ]
Chandramouli, G. V. P. [1 ]
机构
[1] Natl Inst Technol, Dept Chem, Warangal 506004, Andhra Pradesh, India
关键词
One-pot synthesis; Multi-component reaction; bmim]BF4; Chromeno[2,3-d]pyrimidin-8-amine; Antibacterial activity; Single-crystal X-ray diffraction; INHIBITORS; APOPTOSIS; COMPOUND; PROTEIN;
D O I
10.1016/j.molstruc.2012.02.044
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
An efficient, simple and convenient method for the one-pot multi-component synthesis of novel chromeno[2,3-d]pyrimidin-8-amine derivatives has been accomplished by starting from alpha-naphthol, aryl aldehydes, malononitrile and NH4Cl. The reaction has been catalyzed by 1-butyl-3-methylimidazolium tetrafluoroborate [bmim]BF4 ionic liquid. The newly synthesized compounds were characterized by IR, H-1 NMR, C-13 NMR, mass spectra, and elemental analysis. The structure of compound 4a was confirmed by single-crystal X-ray diffraction. All the synthesized compounds were evaluated for their in vitro antibacterial activity. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码:60 / 64
页数:5
相关论文
共 42 条
  • [1] Synthesis of 2,4,6-trisubstituted pyrimidines as antimalarial agents
    Agarwal, A
    Srivastava, K
    Puri, SK
    Chauhan, PMS
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (15) : 4645 - 4650
  • [2] Novel pyrazolo[3,4-d]pyrimidine-based inhibitors of Staphlococcus aureus DNA polymerase III:: Design, synthesis, and biological evaluation
    Ali, A
    Taylor, GE
    Ellsworth, K
    Harris, G
    Painter, R
    Silver, LL
    Young, K
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (10) : 1824 - 1830
  • [3] One-pot synthesis of arylsulfonamides and azetidine-2,4-diones via multicomponent reaction of an amine, an acetylenic compound, and an arylsuffonyl isocyanate
    Alizadeh, Abdolali
    Rezvanian, Atieh
    [J]. SYNTHESIS-STUTTGART, 2008, (11): : 1747 - 1752
  • [4] Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)
    Anderson, DR
    Hegde, S
    Reinhard, E
    Gomez, L
    Vernier, WF
    Lee, L
    Liu, S
    Sambandam, A
    Snider, PA
    Masih, L
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (06) : 1587 - 1590
  • [5] [Anonymous], 2000, SHELXTL PROGR SOL RE
  • [6] Barbour L.J., 2001, J SUPRAMOL CHEM, V1, P189, DOI [DOI 10.1016/S1472-7862(02)00030-8, 10.1016/S1472-7862(02)00030-8]
  • [7] ASYMMETRIC-SYNTHESIS .3. SYNTHESIS OF (2R)-(+)-2,3-DIHYDRO-2,6-DIMETHYL-4H-PYRAN-4-ONE, A HOMOLOG OF PHEROMONES OF A SPECIES IN THE HEPIALIDAE FAMILY
    BIANCHI, G
    TAVA, A
    [J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1987, 51 (07): : 2001 - 2002
  • [8] Collin C H, 1964, MICROBIOLOGICAL METH, P92
  • [9] Dell C. P., 1993, CHEM ABSTR, Patent No. [EP 537,949, EP 537949]
  • [10] Desiraju G. R., 1999, The Weak Hydrogen Bond