1H-吡唑并[3,4-b]喹啉,6-氯-3-甲基-1,4-二苯基- | 133175-88-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 1H-吡唑并[3,4-b]喹啉,6-氯-3-甲基-1,4-二苯基-
• 英文名称: 6-chloro-3-methyl-1,4-diphenyl-1H-pyrazolo[3,4-b]quinoline
• 英文别名: 6-chloro-3-methyl-1,4-diphenylpyrazolo[3,4-b]quinoline
• CAS: 133175-88-9
• 化学式: C₂₃H₁₆ClN₃
• 分子量: 369.853
• InChiKey: KGOHKGRCZPJHQC-UHFFFAOYSA-N

物化性质

• 熔点：
  193-194 °C
• 沸点：
  506.6±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(6-氯-2-羟基-4-苯基-喹啉-3-基)-乙酮 、 苯肼 在 indium(III) chloride 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以86%的产率得到1H-吡唑并[3,4-b]喹啉,6-氯-3-甲基-1,4-二苯基-
  参考文献：
  名称：

  Object-oriented synthetic approach toward angular and linear fused pyrazoloquinolines of biological importance with InCl₃catalyst

  摘要：

  A simple and short approach for the synthesis of pyrazolo[3,4-b]quinoline (3a-3p) and pyrazolo[4,3-c]quinoline (6a-6h) using various Lewis acid catalysts was developed. InCl3 was found to be more effective in providing greater yield of products compared to Yb(OTf)(3), Sc(OTf)(3), SnCl4, AlCl3, TiCl4, ZnCl2, FeCl3, and BF3 center dot Et2O. Moreover, a comparison of conventional and microwave methods has revealed that the latter method is more efficient compared to former one. Structures were confirmed by Fourier transform infrared, mass spectrometry, H-1 and C-13 NMR, X-ray crystallography, and elemental analyses. All of the synthesized compounds were evaluated for alpha-glucosidase inhibitory activity. Compounds 3a, 3p, 3i, 3h, 3k, 3o, and 3g exhibited anti alpha-glucosidase inhibitory activity with IC50 values of 57.5, 60.3, 65.9, 71.9, 80.8, 123.7, and 126.4 mu M, respectively, which is quite comparable to the standard drug acarbose (IC50=115.8 mu M).

  DOI：

  10.1080/00397911.2015.1133827

文献信息

• Chaczatrian; Chaczatrian; Danel, Polish Journal of Chemistry, 2003, vol. 77, # 9, p. 1141 - 1147
  作者：Chaczatrian、Chaczatrian、Danel、Tomasik

  DOI：——

  日期：——
• Hennig, L.; Mueller, T.; Grosche, M., Journal fur praktische Chemie (Leipzig 1954), 1990, vol. 332, # 5, p. 693 - 698
  作者：Hennig, L.、Mueller, T.、Grosche, M.

  DOI：——

  日期：——
• Object-oriented synthetic approach toward angular and linear fused pyrazoloquinolines of biological importance with InCl₃catalyst
  作者：Thangaraj Arasakumar、Sadasivam Mathusalini、Krishnasamy Lakshmi、Palathurai Subramaniam Mohan、Athar Ata、Chia-Her Lin

  DOI：10.1080/00397911.2015.1133827

  日期：2016.2

  A simple and short approach for the synthesis of pyrazolo[3,4-b]quinoline (3a-3p) and pyrazolo[4,3-c]quinoline (6a-6h) using various Lewis acid catalysts was developed. InCl3 was found to be more effective in providing greater yield of products compared to Yb(OTf)(3), Sc(OTf)(3), SnCl4, AlCl3, TiCl4, ZnCl2, FeCl3, and BF3 center dot Et2O. Moreover, a comparison of conventional and microwave methods has revealed that the latter method is more efficient compared to former one. Structures were confirmed by Fourier transform infrared, mass spectrometry, H-1 and C-13 NMR, X-ray crystallography, and elemental analyses. All of the synthesized compounds were evaluated for alpha-glucosidase inhibitory activity. Compounds 3a, 3p, 3i, 3h, 3k, 3o, and 3g exhibited anti alpha-glucosidase inhibitory activity with IC50 values of 57.5, 60.3, 65.9, 71.9, 80.8, 123.7, and 126.4 mu M, respectively, which is quite comparable to the standard drug acarbose (IC50=115.8 mu M).