phenyl 1H-indol-5-ylcarbamate | 109737-03-3

• 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: phenyl 1H-indol-5-ylcarbamate
• 英文别名: phenyl N-(1H-indol-5-yl)carbamate
• CAS: 109737-03-3
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: QNGCAJGLRUINME-UHFFFAOYSA-N

物化性质

• 沸点：
  436.2±27.0 °C(Predicted)
• 密度：
  1.350±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phenyl 1H-indol-5-ylcarbamate 在 一水合肼 作用下， 以 乙醇 为溶剂， 以82 %的产率得到4-(1H-indol-5-yl)semicarbazide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of carbonyl-hydrazine-1-carboxamide derivatives as anti-hepatic fibrosis agents targeting Nur77

  摘要：

  DOI：

  10.1016/j.bioorg.2023.106795
• 作为产物：
  描述：

  5-硝基吲哚 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 phenyl 1H-indol-5-ylcarbamate
  参考文献：
  名称：

  Identification of (E)-1-((1H-indol-3-yl)methylene)-4-substitute-thiosemicarbazones as potential anti-hepatic fibrosis agents

  摘要：

  DOI：

  10.1016/j.bioorg.2023.107022

文献信息

• Discovery of CC Chemokine Receptor-3 (CCR3) Antagonists with Picomolar Potency
  作者：George V. De Lucca、Ui Tae Kim、Brian J. Vargo、John V. Duncia、Joseph B. Santella、Daniel S. Gardner、Changsheng Zheng、Ann Liauw、Zhang Wang、George Emmett、Dean A. Wacker、Patricia K. Welch、Maryanne Covington、Nicole C. Stowell、Eric A. Wadman、Anuk M. Das、Paul Davies、Swamy Yeleswaram、Danielle M. Graden、Kimberly A. Solomon、Robert C. Newton、George L. Trainor、Carl P. Decicco、Soo. S. Ko

  DOI：10.1021/jm049530m

  日期：2005.3.1

  Starting with our previously described(20) class of CC chemokine receptor-3 (CCR3) antagonist, we improved the potency by replacing the phenyl linker of 1 with a cyclohexyl linker and by replacing the 4-benzylpiperidine with a 3-benzylpiperidine. The resulting compound, 32, is a potent and selective antagonist of CCR3. SAR studies showed that the 3-acetylphenyl urea of 32 could be replaced with heterocyclic ureas or heterocyclic-substituted phenyl ureas and still maintain the potency (inhibition of eotaxin-induced chemotaxis) of this class of compounds in the low-picomolar range (IC50 = 10-60 pM), representing some of the most potent CCR3 antagonists reported to date. The potency of 32 for mouse CCR3 (chemotaxis IC50 = 41 nM) and its oral bioavailability in mice (20% F) were adequate to assess the efficacy in animal models of allergic airway inflammation. Oral administration of 32 reduced eosinophil recruitment into the lungs in a dose-dependent manner in these animal models. On the basis of its overall potency, selectivity, efficacy, and safety profile, the benzenesulfonate salt of 32, designated DPC168, entered phase 1 clinical trials.
• Discovery of Potent and Selective Transient Receptor Potential Vanilloid 1 (TRPV1) Agonists with Analgesic Effects <i>In Vivo</i> Based on the Functional Conversion Induced by Altering the Orientation of the Indazole Core
  作者：Qianqian Liang、Zhen Qiao、Qiqi Zhou、Dengqi Xue、KeWei Wang、Liming Shao

  DOI：10.1021/acs.jmedchem.2c00469

  日期：2022.9.8
• Design, synthesis, and biological evaluation of carbonyl-hydrazine-1-carboxamide derivatives as anti-hepatic fibrosis agents targeting Nur77
  作者：Hongyu Hu、Gang Lin、Fengming He、Jie Liu、Rong Jia、Kun Li、Wenbin Hong、Meijuan Fang、Jin-Zhang Zeng

  DOI：10.1016/j.bioorg.2023.106795

  日期：2023.11
• Identification of (E)-1-((1H-indol-3-yl)methylene)-4-substitute-thiosemicarbazones as potential anti-hepatic fibrosis agents
  作者：Gang Lin、Yijing Zhong、Shengwei Hu、Fengming He、Zhaolin Zhang、Weibi Li、Hongyu Hu、Jin-Zhang Zeng

  DOI：10.1016/j.bioorg.2023.107022

  日期：2024.2