(5-bromo-1-ethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)propanedinitrile | 330833-67-5

• 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: (5-bromo-1-ethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)propanedinitrile
• 英文别名: 2-(5-bromo-1-ethyl-2-oxoindol-3-ylidene)propanedinitrile
• CAS: 330833-67-5
• 化学式: C₁₃H₈BrN₃O
• 分子量: 302.13
• InChiKey: JIGHJGNWXWJXGK-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：

  碳酸二稀丙酯 、 (5-bromo-1-ethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)propanedinitrile 在 bis(η3-allyl-μ-chloropalladium(II)) 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以55%的产率得到2-allyl-2-[3-(allyloxy)-5-bromo-1-ethyl-2-oxoindolin-3-yl]malononitrile
  参考文献：
  名称：

  Isatylidenes 的钯催化双功能化：通往 Spiro-Indol-2-ones 的简便途径

  摘要：

  通过利用两亲性双-π-烯丙基钯和相关中间体，开发了一种有效的协议，用于从 isatylidenes 构建 3,3-二取代 indol-2-ones。所开发的策略是一种将 indol-2-one 的 3 位季铵化为双取代的功能化 indol-2-one 的新方法。这些产物经过闭环复分解反应合成螺[环己烯-1,3'-吲哚]-2'-酮和螺[oxep​​-5-ene-2,3'-吲哚]-2'-酮，具有生物学意义。

  DOI：

  10.1002/ejoc.201000604
• 作为产物：
  描述：

  丙二腈 、 5-溴-1-乙基-1H-吲哚-2,3-二酮 在 calcium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 (5-bromo-1-ethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)propanedinitrile
  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

文献信息

• Design, synthesis and evaluation of structurally diverse chrysin-chromene-spirooxindole hybrids as anticancer agents
  作者：Wen-Hui Zhang、Shuang Chen、Xiong-Li Liu、Ting-Ting Feng、Wu-De Yang、Ying Zhou

  DOI：10.1016/j.bmc.2019.115109

  日期：2019.11

  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.
• Palladium-Catalyzed Bis-Functionalization of Isatylidenes: A Facile Route towards Spiro-Indol-2-ones
  作者：Sholly Clair George、Jubi John、Saithalavi Anas、Joshni John、Yoshinori Yamamoto、Eringathodi Suresh、K. V. Radhakrishnan

  DOI：10.1002/ejoc.201000604

  日期：——

  construction of 3,3-disubstituted indol-2-ones from isatylidenes by utilizing amphiphilic bis-π-allylpalladium and related intermediates. The developed strategy is a new method for the quaternization of position 3 of the indol-2-one towards disubstituted functionalized indol-2-ones. These products were subjected to ring-closing metathesis towards the synthesis of spiro[cyclohexene-1,3′-indol]-2′-ones

  通过利用两亲性双-π-烯丙基钯和相关中间体，开发了一种有效的协议，用于从 isatylidenes 构建 3,3-二取代 indol-2-ones。所开发的策略是一种将 indol-2-one 的 3 位季铵化为双取代的功能化 indol-2-one 的新方法。这些产物经过闭环复分解反应合成螺[环己烯-1,3'-吲哚]-2'-酮和螺[oxep​​-5-ene-2,3'-吲哚]-2'-酮，具有生物学意义。