4-bromo-N-[2-(1H-indol-3-yl)ethyl]benzamide | 57691-97-1

• 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: 4-bromo-N-[2-(1H-indol-3-yl)ethyl]benzamide
• 英文别名: N-(2-(1 H-indol-3-yl)ethyl)-4-bromobenzamide
• CAS: 57691-97-1
• 化学式: C₁₇H₁₅BrN₂O
• 分子量: 343.223
• InChiKey: SUTWXMRWCAFANX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-N-[2-(1H-indol-3-yl)ethyl]benzamide 、 4-叔丁基苯硼酸 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61%的产率得到N-(2-(1H-Indol-3-yl)ethyl)-4''-tert-butylbiphenyl-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
• 作为产物：
  描述：

  色胺 、 4-溴苯甲酰氯 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到4-bromo-N-[2-(1H-indol-3-yl)ethyl]benzamide
  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

• <i>N</i>-Heterocyclic Carbene-Mediated Microfluidic Oxidative Electrosynthesis of Amides from Aldehydes
  作者：Robert A. Green、Derek Pletcher、Stuart G. Leach、Richard C. D. Brown

  DOI：10.1021/acs.orglett.6b00339

  日期：2016.3.4

  A flow process for N-Heterocyclic Carbene (NHC)-mediated anodic oxidative amidation of aldehydes is described, employing an undivided microfluidic electrolysis cell to oxidize Breslow intermediates. After electrochemical oxidation, the reaction of the intermediate N-acylated thiazolium cation with primary amines is completed by passage through a heating cell to achieve high conversion in a single pass

  描述了一种N-杂环卡宾（NHC）介导的醛的阳极氧化酰胺化的工艺，该工艺采用未分开的微流体电解槽氧化Breslow中间体。电化学氧化后，中间体N-酰化噻唑鎓阳离子与伯胺的反应通过通过加热单元以单次实现高转化率来完成。流动混合方案避免了醛和胺底物之间竞争性亚胺形成的问题，否则将阻止所需产物的形成。对于19种酰胺，实现了高收率（71–99％），生产率（高达2.6 gh –1）和电流效率（65–91％）。
• [EN] FASCAPLYSIN DERIVATIVES AND THEIR USE IN THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS DE FASCAPLYSINE ET LEUR UTILISATION DANS LE TRAITEMENT D'UN CANCER
  申请人：UNIV MONTFORT

  公开号：WO2009022104A1

  公开（公告）日：2009-02-19

  A method of treating cancer comprising administering a compound of Formula (I), (II) or (III) to a patient.

  一种治疗癌症的方法，包括向患者给予化合物I、II或III的剂量。
• Espejo, Vinson R.; Rainier, Jon D., Journal of the American Chemical Society, 2008, vol. 130, p. 12894 - 12895
  作者：Espejo, Vinson R.、Rainier, Jon D.

  DOI：——

  日期：——
• 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.