1-(4-aminophenyl)-2-(pyridin-3-yl)ethane-1,2-dione | 1259524-89-4

• 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: 1-(4-aminophenyl)-2-(pyridin-3-yl)ethane-1,2-dione
• 英文别名: 1-(4-Aminophenyl)-2-pyridin-3-ylethane-1,2-dione
• CAS: 1259524-89-4
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: MPIAROLOKMJZIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  tert-butyl (4-(2-oxo-2-(pyridin-2-yl)acetyl)phenyl)carbamate 在 甲醇 、 乙酰氯 作用下， 以60%的产率得到1-(4-aminophenyl)-2-(pyridin-3-yl)ethane-1,2-dione
  参考文献：
  名称：

  Structure−Activity Relationships of Substituted 1-Pyridyl-2-phenyl-1,2-ethanediones: Potent, Selective Carboxylesterase Inhibitors

  摘要：

  Inhibition of intestinal carboxylesterases may allow modification of the pharmacokinetics/pharmacodynamic profile of existing drugs by altering half-life or toxicity. Since previously identified diarylethane-1,2-dione inhibitors are decidedly hydrophobic, a modified dione scaffold was designed and elaborated into a > 300 member library, which was subsequently screened to establish the SAR for esterase inhibition. This allowed the identification of single digit nanomolar hiCE inhibitors that showed improvement in selectivity and measured solubility.

  DOI：

  10.1021/jm101101q

文献信息

• One-Pot Synthesis of<i>p</i>-Amino-Substituted Unsymmetrical Benzils and Benzil Derivatives
  作者：Hongjin Zhang、Xiangwei Ren、Wentao Zhao、Xiangyang Tang、Guangwei Wang

  DOI：10.1002/adsc.201600389

  日期：2017.2.2

  An efficient iodine/copper(II) oxide co‐promoted direct oxidative coupling of anilines and methyl aryl ketones has been developed for the synthesis of p‐amino‐substituted unsymmetrical benzils and their iodo‐substituted derivatives. The chemoselectivity of the reactions can be easily controlled by adjusting the amount of iodine. This method exhibits good functional group tolerance for various substituents

  已开发出一种高效的碘/铜（II）共同促进苯胺和甲基芳基酮的直接氧化偶联反应，用于合成对氨基取代的不对称苯及其碘取代的衍生物。通过调节碘的量，可以容易地控制反应的化学选择性。该方法对甲基芳基酮的芳环上的各种取代基表现出良好的官能团耐受性。已经基于对照实验提出了该反应的可能机理。从苯甲醚产品中合成了几个代表性的喹喔啉，以证明该方法的实用性。
• Structure−Activity Relationships of Substituted 1-Pyridyl-2-phenyl-1,2-ethanediones: Potent, Selective Carboxylesterase Inhibitors
  作者：Brandon M. Young、Janice L. Hyatt、David C. Bouck、Taosheng Chen、Parimala Hanumesh、Jeanine Price、Vincent A. Boyd、Philip M. Potter、Thomas R. Webb

  DOI：10.1021/jm101101q

  日期：2010.12.23

  Inhibition of intestinal carboxylesterases may allow modification of the pharmacokinetics/pharmacodynamic profile of existing drugs by altering half-life or toxicity. Since previously identified diarylethane-1,2-dione inhibitors are decidedly hydrophobic, a modified dione scaffold was designed and elaborated into a > 300 member library, which was subsequently screened to establish the SAR for esterase inhibition. This allowed the identification of single digit nanomolar hiCE inhibitors that showed improvement in selectivity and measured solubility.