2-(1H-indole-3-carbonyl)-3-(pyridin-3-yl)acrylonitrile | 1097563-80-8

• 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: 2-(1H-indole-3-carbonyl)-3-(pyridin-3-yl)acrylonitrile
• 英文别名: 2-(1H-indole-3-carbonyl)-3-pyridin-3-ylprop-2-enenitrile
• CAS: 1097563-80-8
• 化学式: C₁₇H₁₁N₃O
• 分子量: 273.294
• InChiKey: IISJXCBJRHDVLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.54
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-氨基-3-甲基-1-苯基吡唑 、 2-(1H-indole-3-carbonyl)-3-(pyridin-3-yl)acrylonitrile 反应 0.15h， 生成 6-(1H-indol-3-yl)-4-(3-pyridil)-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile
  参考文献：
  名称：

  Regioselective Three-Component Synthesis of Indolylpyrazolo[3,4- b]pyridines Induced by Microwave and under Solvent-Free Conditions

  摘要：

  新型 4-(1H-吲哚-3-基)-6-芳基吡唑并[3,4-b]吡啶 7 是由 5-氨基吡唑 1、苯甲醛 2 和 3-吲哚基-3-氧代丙腈 5 通过微波诱导的无溶剂三组分反应制备的。这些化合物也是通过氨基吡唑 1 与 3-(1H-吲哚-3-基)-3-氧代丙腈和醛反应制备的 3-(1H-吲哚-3-基)-3-氧代丙腈 6 的亚苄基衍生物反应得到的。

  DOI：

  10.2174/157017809788681284
• 作为产物：
  描述：

  3-吡啶甲醛 、 3-(1H-吲哚-3-基)-3-氧丙腈 反应 0.1h， 以88%的产率得到2-(1H-indole-3-carbonyl)-3-(pyridin-3-yl)acrylonitrile
  参考文献：
  名称：

  Regioselective Three-Component Synthesis of Indolylpyrazolo[3,4- b]pyridines Induced by Microwave and under Solvent-Free Conditions

  摘要：

  新型 4-(1H-吲哚-3-基)-6-芳基吡唑并[3,4-b]吡啶 7 是由 5-氨基吡唑 1、苯甲醛 2 和 3-吲哚基-3-氧代丙腈 5 通过微波诱导的无溶剂三组分反应制备的。这些化合物也是通过氨基吡唑 1 与 3-(1H-吲哚-3-基)-3-氧代丙腈和醛反应制备的 3-(1H-吲哚-3-基)-3-氧代丙腈 6 的亚苄基衍生物反应得到的。

  DOI：

  10.2174/157017809788681284

文献信息

• Design and synthesis of spirooxindole–pyrrolidines embedded with indole and pyridine heterocycles by multicomponent reaction: anticancer and <i>in silico</i> studies
  作者：Sivakalai Mayakrishnan、Devarajan Kathirvelan、Yuvaraj Arun、Krishnan Saranraj、Chandrasekaran Balachandran、Shin Aoki、Pannerselvam Yuvaraj、Narayanan Uma Maheswarai

  DOI：10.1039/d1nj05839h

  日期：——

  environment-friendly route for synthesizing a series of spirooxindoles using the 1,3-dipolar cycloaddition reaction of a dipolarophile with in situ generated azomethine ylide using ethanol as a solvent without any catalyst. The reaction offers potent biologically active spirooxindole fused with indole and pyridine heterocycles in good to excellent yield (69–94%) with higher diastereoselectivity. These synthesized

  由于现有抗癌药物的缺点，有必要为全球药物化学研究人员寻找更有效和选择性的抗癌药物。螺氧吲哚被视为特权支架，因为它们存在于许多天然产物和生物活性分子中。在此，我们报告了一种高效、环保的合成一系列螺氧吲哚类化合物的路线，该路线使用偶极试剂与原位生成的偶氮甲碱叶立德的 1,3-偶极环加成反应，使用乙醇作为溶剂，无需任何催化剂。该反应提供了与吲哚和吡啶杂环稠合的有效生物活性螺氧吲哚，产率从良好到极好（69-94%），非对映选择性更高。这些合成的化合物（4a-x) 使用 MTT 测定法使用 A549、HepG-2 和 SKOV-3 癌细胞系筛选抗癌活性。在所有筛选的化合物中，4u和4w在低于10 μg mL -1时显示出对HepG-2 细胞的显着细胞毒活性。与 Bcl-2 和 ALK 受体的分子对接研究表明，对于4u和4w以及4c和4o观察到更高的结合能，其值分别为 -6.56 和 -8.41、-6
• Indole acrylonitriles as potential anti-hyperglycemic agents: Synthesis, α-glucosidase inhibitory activity and molecular docking studies
  作者：Mehwish Solangi、Kanwal、Khalid Mohammed Khan、Faiza Saleem、Shehryar Hameed、Jamshed Iqbal、Zainab Shafique、Urooj Qureshi、Zaheer Ul-Haq、Muhammad Taha、Shahnaz Perveen

  DOI：10.1016/j.bmc.2020.115605

  日期：2020.11

  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.