2-(1H-indole-3-carbonyl)-3-(2-methylphenyl)prop-2-enenitrile | 1012927-93-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-(1H-indole-3-carbonyl)-3-(2-methylphenyl)prop-2-enenitrile
• CAS: 1012927-93-3
• 化学式: C₁₉H₁₄N₂O
• 分子量: 286.333
• InChiKey: JVZZLTWWAQAJAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  56.65
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(1H-indole-3-carbonyl)-3-(2-methylphenyl)prop-2-enenitrile 、 N-苯甲酰甲基溴吡啶 在 三乙胺 作用下， 以 水 为溶剂， 反应 1.5h， 以87%的产率得到trans-5-benzoyl-2-(1H-3-indolyl)-4-(2-methylphenyl)-4,5-dihydro-3-furancarbonitrile
  参考文献：
  名称：

  Domino reactions in water: diastereoselective synthesis of densely functionalized indolyldihydrofuran derivatives

  摘要：

  反式-5-芳酰基-2-(吲哚-3-基)-4-芳基-4,5-二氢呋喃-3-甲腈化合物库是由 2-(3-吲哚羰基)-3-芳基-2-丙烯腈与(2-芳基-2-氧代乙基)溴化吡啶鎓在三乙胺存在下通过一个简单、易操作的多米诺过程在水中非对映选择性合成的，产量极佳。由于只需从水性反应介质中过滤并重结晶最终产物，因此避免了萃取和色谱步骤。这种一锅转化生成了一个 C-C 键和一个 C-O 键，并可能通过多米诺顺序进行，包括生成吡啶鎓酰亚胺、迈克尔加成和通过分子内亲核取代最终环化。

  DOI：

  10.1039/c2gc16517a
• 作为产物：
  描述：

  3-(1H-吲哚-3-基)-3-氧丙腈 、 2-甲基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-(1H-indole-3-carbonyl)-3-(2-methylphenyl)prop-2-enenitrile
  参考文献：
  名称：

  Indole acrylonitriles as potential anti-hyperglycemic agents: Synthesis, α-glucosidase inhibitory activity and molecular docking studies

  摘要：

  One of the most prevailing metabolic disorder diabetes mellitus has become the global health issue that has to be addressed and cured. Different marketed drugs have been made available for the treatment of diabetes but there is still a need of introducing new therapeutic agents that are economical and have lesser or no side effects. The current study deals with the synthesis of indole acrylonitriles (3-23) and the evaluation of these compounds for their potential for alpha-glucosidase inhibition. The structures of these synthetic molecules were deduced by using different spectroscopic techniques. Acarbose (IC50 = 2.91 +/- 0.02 mu M) was used as standard in this study and the synthetic molecules (3-23) have shown promising alpha-glucosidase inhibitory activity. Compounds 4, 8, 10, 11, 14, 18, and 21 displayed superior inhibition of alpha-glucosidase enzyme in the range of (IC50 = 0.53 +/- 0.01-1.36 +/- 0.04 mu M) as compared to the standard acarbose. Compound 10 (IC50 = 0.53 +/- 0.01 mu M) was the most effective inhibitor of this library and displayed many folds enhanced activity in contrast to the standard. Molecular docking of synthetic compounds was performed to verify the binding interactions of ligand with the active site of enzyme. This study had identified a number of potential alpha-glucosidase inhibitors that can be used for further research to identify a potent therapeutic agent against diabetes.

  DOI：

  10.1016/j.bmc.2020.115605