4-indol-3-ylmethylene-5-methyl-2-p-tolyl-2,4-dihydro-pyrazol-3-one | 43106-27-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-indol-3-ylmethylene-5-methyl-2-p-tolyl-2,4-dihydro-pyrazol-3-one
• 英文别名: 4-indol-3-ylmethylene-5-methyl-2-p-tolyl-2,4-dihydro-pyrazol-3-one
• CAS: 43106-27-0
• 化学式: C₂₀H₁₇N₃O
• mdl: MFCD01157749
• 分子量: 315.374
• InChiKey: KIUIFOGWOCSNBD-UHFFFAOYSA-N

物化性质

• 沸点：
  537.6±60.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  48.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-indol-3-ylmethylene-5-methyl-2-p-tolyl-2,4-dihydro-pyrazol-3-one 在 aluminum (III) chloride 、 sodium hydride 作用下， 以 二氯甲烷 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 13.5h， 生成 4-((1-(2-hydroxy-3-(3-morpholinopropylamino)propyl)-1H-indol-3-yl)methylene)-3-methyl-1-p-tolyl-1H-pyrazol-5(4H)-one
  参考文献：
  名称：

  The discovery of indole derivatives as novel hepatitis C virus inhibitors

  摘要：

  In this study, a library of in-house small molecule was screened using a HCV cell-based assay and a compound (1) containing an N-protected indole scaffold (NINS) was identified as a novel anti-HCV inhibitor. Through structure activity relationship (SAR) study, it was observed that the racemic inhibitor (10m) displayed good anti-HCV activity (EC50 = 1.02 +/- 0.10 mu M) with the excellent selectivity index (SI = 45.56). Interestingly, R-enantiomer ((R)-10m) showed better anti-HCV activity and lower cytotoxicity than S-enantiomer ((S)-10m). (R)-10m gave the best anti-HCV potency (EC50 = 0.72 +/- 0.09 mu M) with the highest selectivity index (SI > 69.44). In addition, the mechanism of action study of NINS derivatives demonstrated that NINS derivatives interfere with the early step (viral entry) of the HCV life cycle. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.062
• 作为产物：
  描述：

  对甲基苯肼 在 哌啶 作用下， 以 甲醇 、 正丁醇 为溶剂， 生成 4-indol-3-ylmethylene-5-methyl-2-p-tolyl-2,4-dihydro-pyrazol-3-one
  参考文献：
  名称：

  The discovery of indole derivatives as novel hepatitis C virus inhibitors

  摘要：

  In this study, a library of in-house small molecule was screened using a HCV cell-based assay and a compound (1) containing an N-protected indole scaffold (NINS) was identified as a novel anti-HCV inhibitor. Through structure activity relationship (SAR) study, it was observed that the racemic inhibitor (10m) displayed good anti-HCV activity (EC50 = 1.02 +/- 0.10 mu M) with the excellent selectivity index (SI = 45.56). Interestingly, R-enantiomer ((R)-10m) showed better anti-HCV activity and lower cytotoxicity than S-enantiomer ((S)-10m). (R)-10m gave the best anti-HCV potency (EC50 = 0.72 +/- 0.09 mu M) with the highest selectivity index (SI > 69.44). In addition, the mechanism of action study of NINS derivatives demonstrated that NINS derivatives interfere with the early step (viral entry) of the HCV life cycle. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.062