5,7-ditrifluoromethyl-3-phenylpyrazolo<1,5-a>pyrimidine | 70594-15-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5,7-ditrifluoromethyl-3-phenylpyrazolo<1,5-a>pyrimidine
• 英文别名: 3-phenyl-5,7-bis(trifluoromethyl)pyrazolo[1,5-a]pyrimidine
• CAS: 70594-15-9
• 化学式: C₁₄H₇F₆N₃
• 分子量: 331.22
• InChiKey: QGZOMUVIDLHZOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-甲酸基-2-苯基乙腈 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 5,7-ditrifluoromethyl-3-phenylpyrazolo<1,5-a>pyrimidine
  参考文献：
  名称：

  Synthesis and biological evaluation of 7-trifluoromethylpyrazolo[1,5- a ]pyrimidines as anti-inflammatory and antimicrobial agents

  摘要：

  A series of 2-H/methyl-3-phenyl-5-alkyl/aryl/heteroaryl-7-trifluoromethylpyrazolo[1,5-alpha]pyrimidines (4a-l) were synthesized by refluxing 3(5)-amino-4-phenyl-5(3)-H/methyl-1H-pyrazoles (12) with trifluoromethyl-beta-diketones (3a-f) in ethanol for 6 h. The structure of the compounds was assigned on the basis of H-1, C-13, F-19 NMR and IR spectral data. The intermediate, 5-methyl-4-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-alpha]pyrimidin-5,7-diol (5b), involved in the reaction was also isolated and characterized in one case by performing the reaction in DCM at -15 degrees C. A total of nine compounds 4a-f, 4h-i, 4k were tested for their anti-inflammatory activity by Carrageenan-induced rat paw edema assay. Compound 4e exhibited the comparable anti-inflammatory activity (83.4%) to the standard drug Indomethacin (84.2%). To rationalize the anti-inflammatoy activity, docking experiments were performed to study the ability of these compounds to bind into the active site of COX-2 enzyme. All the twelve compounds synthesized (4a-l) were screened for their antimicrobial activity in vitro against two Gram +ve, two Gram -ve bacteria and two fungi. Preliminary results reveal that some of the synthesized compounds revealed promising antimicrobial activity against Gram +ve bacteria and pathogenic fungi used in this study. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.08.017

文献信息

• Balicki, Roman, Polish Journal of Chemistry, 1981, vol. 55, # 10, p. 1995 - 2005
  作者：Balicki, Roman

  DOI：——

  日期：——
• JOSHI K. C.; DUBEY K., J. PRAKT. CHEM., 1979, 321, NO 2, 341-344
  作者：JOSHI K. C.、 DUBEY K.

  DOI：——

  日期：——
• BALICKI, R., POL. J. CHEM., 1981, 55, N 10, 1995-2005
  作者：BALICKI, R.

  DOI：——

  日期：——
• Synthesis and biological evaluation of 7-trifluoromethylpyrazolo[1,5- a ]pyrimidines as anti-inflammatory and antimicrobial agents
  作者：Ranjana Aggarwal、Eakta Masan、Pawan Kaushik、Dhirender Kaushik、Chetan Sharma、K.R. Aneja

  DOI：10.1016/j.jfluchem.2014.08.017

  日期：2014.12

  A series of 2-H/methyl-3-phenyl-5-alkyl/aryl/heteroaryl-7-trifluoromethylpyrazolo[1,5-alpha]pyrimidines (4a-l) were synthesized by refluxing 3(5)-amino-4-phenyl-5(3)-H/methyl-1H-pyrazoles (12) with trifluoromethyl-beta-diketones (3a-f) in ethanol for 6 h. The structure of the compounds was assigned on the basis of H-1, C-13, F-19 NMR and IR spectral data. The intermediate, 5-methyl-4-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-alpha]pyrimidin-5,7-diol (5b), involved in the reaction was also isolated and characterized in one case by performing the reaction in DCM at -15 degrees C. A total of nine compounds 4a-f, 4h-i, 4k were tested for their anti-inflammatory activity by Carrageenan-induced rat paw edema assay. Compound 4e exhibited the comparable anti-inflammatory activity (83.4%) to the standard drug Indomethacin (84.2%). To rationalize the anti-inflammatoy activity, docking experiments were performed to study the ability of these compounds to bind into the active site of COX-2 enzyme. All the twelve compounds synthesized (4a-l) were screened for their antimicrobial activity in vitro against two Gram +ve, two Gram -ve bacteria and two fungi. Preliminary results reveal that some of the synthesized compounds revealed promising antimicrobial activity against Gram +ve bacteria and pathogenic fungi used in this study. (C) 2014 Elsevier B.V. All rights reserved.