p-Toluenesulfonic acid-catalyzed solvent-free synthesis and biological evaluation of new 1-(4-6-dimethylpyrimidin-2-yl)-5-amino-4H-3-arylpyrazole derivatives

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• 作者：Ranjana Aggarwal (1)
  Anshul Bansal (1)
  Isabel Rozas (2)
  Elena Diez-Cecilia (2)
  Amanjot Kaur (3)
  Ritu Mahajan (3)
  Jitender Sharma (3)
  
• 关键词：Solvent ; free synthesis ; 1 ; (4-6-Dimethylpyrimidin ; 2-yl) ; 5 ; amino ; 4H ; 3 ; arylpyrazoles ; N ; acetamide/trifluoroacetamide derivatives ; p ; Toluenesulfonic acid ; Antibacterial activity ; Cytotoxicity
• 刊名：Medicinal Chemistry Research
• 出版年：2014
• 出版时间：March 2014
• 年：2014
• 卷：23
• 期：3
• 页码：1454-1464
• 全文大小：404 KB
• 作者单位：Ranjana Aggarwal (1)
  Anshul Bansal (1)
  Isabel Rozas (2)
  Elena Diez-Cecilia (2)
  Amanjot Kaur (3)
  Ritu Mahajan (3)
  Jitender Sharma (3)
  
  1. Department of Chemistry, Kurukshetra University, Kurukshetra, 136 119, India
  2. Trinity Biomedical Sciences Institute, School of Chemistry, Trinity College Dublin, 154-160 Pearse St., Dublin 2, Ireland
  3. Department of Biotechnology, Kurukshetra University, Kurukshetra, 136 119, India
  
• ISSN：1554-8120

文摘

A solvent-free quick synthesis of 1-(4-6-dimethylpyrimidin-2-yl)-5-amino-4H-3-arylpyrazoles (3) was accomplished by grinding 2-hydrazino-4,6-dimethylpyrimidine (1) and β-ketonitriles (2) in the presence of p-Toluenesulfonic acid as a catalyst. Subsequently, 5-aminopyrazoles (3) were converted to their corresponding N-acetamide (4) and N-trifluoroacetamide (5) derivatives by treating (3) with acetic anhydride/acetic acid and trifluoroacetic anhydride/trifluoroacetic acid, respectively. The newly synthesized compounds were fully characterized using IR, NMR (1H, 13C, and 19F), mass spectral studies, and elemental analyses. All of the fifteen compounds were screened for their in vitro antibacterial activity against two Gram-positive and two Gram-negative pathogenic bacteria such as Bacillus pumilus, Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli, respectively. Additionally, nine of these compounds were screened for their cytotoxicity against the human Caucasian promyelocytic leukemia (HL-60) cell line using the alamarBlue? assay. Preliminary results reveal that compounds 3a, 3b, 3d, 5a, and 5d are showing moderate-to-significant cytotoxic and antibacterial activity.