2-(5-Chloro-1-ethyl-2-oxoindol-3-ylidene)propanedinitrile

• 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-(5-Chloro-1-ethyl-2-oxoindol-3-ylidene)propanedinitrile
• 化学式: C₁₃H₈ClN₃O
• 分子量: 257.679
• InChiKey: UEUPHRKHMYRQEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2,4-dimethoxyphenyl)-5,7-dihydroxy-4H-chromen-4-one 、 2-(5-Chloro-1-ethyl-2-oxoindol-3-ylidene)propanedinitrile 以 甲醇 为溶剂， 反应 8.0h， 生成 2′-amino-5-chloro-8′-(2,4-dimethoxyphenyl)-1-ethyl-5′-hydroxy-2,6′-dioxo-6′H-spiro [indoline-3,4′-pyrano[3,2-g]chromene]-3′‑carbonitrile
  参考文献：
  名称：

  Design, synthesis and evaluation of structurally diverse chrysin-chromene-spirooxindole hybrids as anticancer agents

  摘要：

  A series of structurally diverse chrysin-chromene-spirooxindole hybrids were designed, synthesized via a Knoevenagel/Michael/cyclization of chrysin and isatylidene malononitrile derivatives through utilizing a hybrid pharmacophore approach. The newly synthesized compounds were evaluated for their in vitro anticancer activity, and most of the compounds showed stronger anti-proliferative activity than parent compound chrysin. In particular, compound 3e had the highest cytotoxicity towards A549 cells (IC50 = 3.15 +/- 0.51 mu M), and had better selectivity in A549 cells and normal MRC-5 cells. Furthermore, compound 3e could significantly inhibit the proliferation and migration of A549 cells in a dose-dependent manner, as well as induce the apoptosis possibly through mitochondria-mediated caspase-3/8/9 activation and multi-target co-regulation of the p53 signaling pathway. Thus, our results provide in vitro evidence that compound 3e may be a potential candidate for the development of new anti-tumour drugs.

  DOI：

  10.1016/j.bmc.2019.115109
• 作为产物：
  描述：

  5-氯靛红 在 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 2-(5-Chloro-1-ethyl-2-oxoindol-3-ylidene)propanedinitrile
  参考文献：
  名称：

  通过连续有机催化迈克尔-多米诺迈克尔/羟醛反应立体选择性合成螺十氢萘吲哚衍生物

  摘要：

  已经开发出一种高度立体选择性的方法，用于合成具有五个连续立体中心（包括两个四取代碳）的螺多环羟吲哚。在基于吡咯烷的有机催化剂和 DBU 进行的连续有机催化下，优化了高度原子经济的 Michael-domino Michael/aldol 反应序列，产生了具有优异立体选择性的各种功能化的螺十氢萘吲哚（>99:1 dr，高达 92%） ee）。

  DOI：

  10.1021/acs.joc.2c01046

文献信息

• Visible-Light-Initiated Oxidative Coupling of Indole and Active Methylene Compounds Using Eosin Y as a Photocatalyst
  作者：Sundaram Singh、Ambuj Kumar Kushwaha、Suresh Kumar Maury、Savita Kumari、Arsala Kamal、Himanshu Kumar Singh、Dhirendra Kumar

  DOI：10.1055/a-1894-8303

  日期：2022.11

  A novel, efficient, mild, and inexpensive photocatalytic approach has been established for the visible-light-initiated oxidative coupling of indole and active methylene compounds using atmospheric air and water as an oxidant in the presence of Eosin Y to give 3-methyleneindolin-2-ones. In this work, only one molecule of malononitrile, ethyl acetoacetate, or dimedone reacts with one molecule of indole

  已经建立了一种新颖、高效、温和且廉价的光催化方法，用于在 Eosin Y 存在下使用大气和水作为氧化剂，在可见光下引发吲哚和活性亚甲基化合物的氧化偶联，得到 3-methyleneindolin-2 -那些。在这项工作中，只有一分子丙二腈、乙酰乙酸乙酯或二甲酮与一分子吲哚反应，但相反，两分子巴比妥酸与一分子吲哚反应。该方法的基本特征是无金属反应、产物收率高、无副产物和使用可再生能源。
• Synthesis of tryptanthrin appended dispiropyrrolidine oxindoles and their antibacterial evaluation
  作者：Sruthi Sudheendran Leena、Abdul Akhir、Deepanshi Saxena、Rahul Maitra、Sidharth Chopra、Ani Deepthi

  DOI：10.1039/d3md00017f

  日期：——

  The synthesis of sixteen tryptanthrin appended dispiropyrrolidine oxindoles, employing [3 + 2] cycloaddition of tryptanthrin-derived azomethine ylides with isatilidenes, and their detailed antibacterial evaluation is described. The in vitro antibacterial activities of the compounds were evaluated against ESKAPE pathogens and clinically relevant drug-resistant MRSA/VRSA strains, from which the bromo-substituted

  描述了采用色胺酮衍生的偶氮甲碱叶立德与伊沙替利烯的[3+2]环加成合成了十六种色胺酮附加的二螺吡咯烷羟吲哚，并描述了它们的详细抗菌评价。评估了化合物对 ESKAPE 病原体和临床相关耐药 MRSA/VRSA 菌株的体外抗菌活性，其中溴代二螺吡咯烷羟吲哚5b (MIC = 0.125 μg mL -1 ) 被发现是一种有效的分子金黄色葡萄球菌ATCC 29213 具有良好的选择性指数。