Carbamic acid,(2,3-dihydro-1h-indol-5-yl)-,phenyl ester | 865538-84-7

• 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: Carbamic acid,(2,3-dihydro-1h-indol-5-yl)-,phenyl ester
• 英文别名: phenyl N-(2,3-dihydro-1H-indol-5-yl)carbamate
• CAS: 865538-84-7
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: UFJUDWVPCGWBDK-UHFFFAOYSA-N

物化性质

• 沸点：
  404.9±45.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Carbamic acid,(2,3-dihydro-1h-indol-5-yl)-,phenyl ester 、 (1R,2S)-2-(((S)-3-(4-fluorobenzyl)piperidin-1-yl)methyl)cyclohexylamine 以 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 1-((1R,2S)-2-(((S)-3-(4-fluorobenzyl)piperidin-1-yl)methyl)cyclohexyl)-3-(indolin-5-yl)urea
  参考文献：
  名称：

  Discovery of CC Chemokine Receptor-3 (CCR3) Antagonists with Picomolar Potency

  摘要：

  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.

  DOI：

  10.1021/jm049530m
• 作为产物：
  描述：

  C₂₀H₂₂N₂O₄ 在 三氟乙酸 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 Carbamic acid,(2,3-dihydro-1h-indol-5-yl)-,phenyl ester
  参考文献：
  名称：

  Oxazolidinone antibacterial agents having a thiocarbonyl functionality

  摘要：

  本发明提供了式1化合物： 或药物可接受的盐，其中A，G和R1如权利要求中所定义，它们是抗菌剂。

  公开号：

  US06342513B1