N-(2-(1H-Indol-3-yl)ethyl)biphenyl-4-carboxamide | 372109-21-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-(1H-Indol-3-yl)ethyl)biphenyl-4-carboxamide
• 英文别名: N-[2-(1H-indol-3-yl)ethyl]-4-phenylbenzamide
• CAS: 372109-21-2
• 化学式: C₂₃H₂₀N₂O
• 分子量: 340.425
• InChiKey: GYEGDDXJVFNDOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-bromo-N-[2-(1H-indol-3-yl)ethyl]benzamide 、 苯硼酸 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 24.0h， 以63%的产率得到N-(2-(1H-Indol-3-yl)ethyl)biphenyl-4-carboxamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of new tryptamine and tetrahydro-β-carboline-based selective inhibitors of CDK4

  摘要：

  We present the design, synthesis and biological activity of a library of substituted (biphenylcarbonyl)-tryptamine and ( biphenylcarbonyl)-tetrahydro-beta-carboline compounds related to the natural product fascaplysin, as novel inhibitors of CDK4/cyclin D1. We show all these molecules, prepared using the Suzuki-Miyaura reaction, being selective inhibitors of CDK4 over CDK2. The most active compounds have a CDK4 IC50 in the range 9-11 mu M, three of them containing the para-biphenyl plus para-substituents supporting the existence of a pi-stacking pocket within the active site of CDK4. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.07.002

文献信息

• An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y
  作者：Suresh Babu Meruva、Akula Raghunadh、Raghavendra Rao Kamaraju、U K Syam Kumar、P K Dubey

  DOI：10.3762/bjoc.10.45

  日期：——

  A novel synthetic methodology has been developed for the synthesis of dihydro-β-carboline derivatives employing oxidative amidation–Bischler–Napieralski reaction conditions using tryptamine and 2,2-dibromo-1-phenylethanone as key starting materials. A number of dihydro-β-carboline derivatives have been synthesized in moderate to good yields using this methodology. Attempts were made towards the conversion of these dihydro-β-carbolines to naturally occurring eudistomin alkaloids.

  一种新的合成方法已经开发出来，用于合成二氢-β-咔啉衍生物，采用氧化酰胺化-Bischler-Napieralski反应条件，使用色胺和2,2-二溴-1-苯乙酮作为关键起始材料。使用这种方法，合成了多种二氢-β-咔啉衍生物，收率在中等到良好之间。尝试将这些二氢-β-咔啉转化为天然存在的尤地斯托明生物碱。
• 一种吲哚衍生物及其制备方法和应用
  申请人：中国医学科学院医药生物技术研究所

  公开号：CN114644583A

  公开（公告）日：2022-06-21

  本发明提供了一种吲哚衍生物及其制备方法和应用，属于有机合成技术领域。本发明提供的吲哚衍生物，具有式I～IV所示结构中的任意一种。本发明提供的吲哚衍生物具有良好的抗菌活性，能够用于制备抗菌药物，尤其是可以作为TrpRS抑制剂应用。本发明提供的吲哚衍生物中吲哚与芳香环之间连接基是硫脲时，吲哚衍生物的抗菌活性优于酰胺类连接基的吲哚衍生物。而且，当芳香环为吸电子基取代的苯环时吲哚衍生物的抗菌活性更好。酶活性及亲和力实验结果表明本发明提供的吲哚衍生物的作用靶点是TrpRS，且对TrpRS的亲和力高，具有进一步临床开发应用的价值，可以作为药物先导分子进一步研究开发。
• Design, synthesis and biological evaluation of new tryptamine and tetrahydro-β-carboline-based selective inhibitors of CDK4
  作者：Paul R. Jenkins、James Wilson、Daniel Emmerson、Marcos D. Garcia、Matthew R. Smith、Stephen J. Gray、Robert G. Britton、Sachin Mahale、Bhabatosh Chaudhuri

  DOI：10.1016/j.bmc.2008.07.002

  日期：2008.8

  We present the design, synthesis and biological activity of a library of substituted (biphenylcarbonyl)-tryptamine and ( biphenylcarbonyl)-tetrahydro-beta-carboline compounds related to the natural product fascaplysin, as novel inhibitors of CDK4/cyclin D1. We show all these molecules, prepared using the Suzuki-Miyaura reaction, being selective inhibitors of CDK4 over CDK2. The most active compounds have a CDK4 IC50 in the range 9-11 mu M, three of them containing the para-biphenyl plus para-substituents supporting the existence of a pi-stacking pocket within the active site of CDK4. (C) 2008 Published by Elsevier Ltd.