4-(4'-methylphenyl)isatin | 1421700-79-9

• 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-(4'-methylphenyl)isatin
• 英文别名: 4-(4-methylphenyl)indoline-2,3-dione；4-(p-tolyl)indoline-2,3-dione
• CAS: 1421700-79-9
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: BJWSELNAUFMCDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(4'-methylphenyl)isatin 在 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 生成 2-(((9-(4'-methylphenyl)-5H-[1,2,4]triazino[5,6-b]indol-3-yl)thio)methyl)benzonitrile
  参考文献：
  名称：

  Ligand-based virtual screening identifies a family of selective cannabinoid receptor 2 agonists

  摘要：

  The cannabinoid receptor 2 (CB2R) has been linked with the regulation of inflammation, and selective receptor activation has been proposed as a target for the treatment of a range of inflammatory diseases such as atherosclerosis and arthritis. In order to identify selective CB2R agonists with appropriate physicochemical and ADME properties for future evaluation in vivo, we first performed a ligand-based virtual screen. Subsequent medicinal chemistry optimisation studies led to the identification of a new class of selective CB2R agonists. Several examples showed high levels of activity (EC50 < 200 nM) and binding affinity (K-i < 200 nM) for the CB2R, and no detectable activity at the CB1R. The most promising example, DIAS2, also showed favourable in vitro metabolic stability and absorption properties along with a clean selectivity profile when evaluated against a panel of GPCRs and kinases. (C) 2014 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/3.0/).

  DOI：

  10.1016/j.bmc.2014.11.002
• 作为产物：
  描述：

  4-溴靛红 、 potassium (4-methylphenyl)trifluoroborate 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium phosphate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以68%的产率得到4-(4'-methylphenyl)isatin
  参考文献：
  名称：

  Ligand-based virtual screening identifies a family of selective cannabinoid receptor 2 agonists

  摘要：

  The cannabinoid receptor 2 (CB2R) has been linked with the regulation of inflammation, and selective receptor activation has been proposed as a target for the treatment of a range of inflammatory diseases such as atherosclerosis and arthritis. In order to identify selective CB2R agonists with appropriate physicochemical and ADME properties for future evaluation in vivo, we first performed a ligand-based virtual screen. Subsequent medicinal chemistry optimisation studies led to the identification of a new class of selective CB2R agonists. Several examples showed high levels of activity (EC50 < 200 nM) and binding affinity (K-i < 200 nM) for the CB2R, and no detectable activity at the CB1R. The most promising example, DIAS2, also showed favourable in vitro metabolic stability and absorption properties along with a clean selectivity profile when evaluated against a panel of GPCRs and kinases. (C) 2014 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/3.0/).

  DOI：

  10.1016/j.bmc.2014.11.002

文献信息

• Efficient synthesis of bulky 4-substituted-isatins via microwave-promoted Suzuki cross-coupling reaction
  作者：Yu-Chao Liu、Chen-Jin Ye、Qiong Chen、Guang-Fu Yang

  DOI：10.1016/j.tetlet.2012.12.021

  日期：2013.2

  Indoline-2,3-diones (isatins) and their derivatives are important heterocycles found in nature and present in numerous bioactive compounds. Very few examples related to the synthesis of 4-substituted-arylisatins have been reported before. Utilizing microwave irradiation, the synthesis of bulky 4-substituted-arylisatins via a Suzuki cross-coupling has been developed with a wide range of substrates. All the reactions proceeded smoothly and afforded moderate to excellent yields of products, which indicating that electronic effects and steric modifications have little effect on this reaction. (C) 2012 Elsevier Ltd. All rights reserved.