3-acetyl-N,N-diallylaniline | 1236376-42-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetyl-N,N-diallylaniline
• 英文别名: 1-[3-[bis(prop-2-enyl)amino]phenyl]ethanone
• CAS: 1236376-42-3
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: GSDFNKZSDAQMGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-acetyl-N,N-diallylaniline 、 5-bromo-2-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Design, synthesis, and evaluation of bromo-retrochalcone derivatives as protein tyrosine phosphatase 1B inhibitors

  摘要：

  A series of bromo-retrochalcones was designed, synthesized and evaluated as PTP1B inhibitors based on licochalcone A and E. Compounds 6, 12, 13, 14, 25, 36, 37, 39, and 41 showed potent inhibitory effects against PTP1B, and compound 37, the most potent among the series, had an IC(50) value of 1.9 mu M, about two-fold better than that of the positive control, ursolic acid. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.057
• 作为产物：
  描述：

  间氨基苯乙酮 、 3-溴丙烯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以84%的产率得到3-acetyl-N,N-diallylaniline
  参考文献：
  名称：

  Optimization of isochromanone based urotensin II receptor agonists

  摘要：

  A series of novel isochromanone based urotensin II receptor agonists have been synthesized and evaluated for their activity using a functional cell based assay (R-SAT). Several potent and efficacious derivatives were identified with 3-(3,4-dichlorophenyl)-6,7-dimethyl-3-(2-dimethylaminoethyl) isochroman-1-one (28) being the most potent compound showing an EC50-value of 51 nM, thereby being the most potent compound so far within the isochromanone series. In addition, two other heterocyclic systems (isochromanes and tetrahydroisoquinolinones) were investigated and these derivatives were found to be both potent and efficacious. The activity of the isochromane derivatives implies that the carbonyl group of the isochromanone is not necessary for activity. Furthermore it was found that the geometry of the heterocycles was more important for receptor interaction than the composition of the heteroatoms present. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.041

文献信息

• Synthesis, biological evaluation, and molecular docking study of novel allyl-retrochalcones as a new class of protein tyrosine phosphatase 1B inhibitors
  作者：Yunjie Zhao、Yongkai Cao、Huizhen Chen、Fei Zhuang、Chao Wu、Goo Yoon、Weiwei Zhu、Ying Su、Suqing Zheng、Zhiguo Liu、Seung Hoon Cheon

  DOI：10.1016/j.bmc.2019.01.034

  日期：2019.3

  We describe herein the design, synthesis, and biological evaluation of a series of novel protein tyrosine phosphatase 1B (PTP1B) inhibitor retrochalcones having an allyl chain at the C-5 position of their B ring. Biological screening results showed that the majority of these compounds exhibited an inhibitory activity against PTP1B. Thus, preliminary structure-activity relationship (SAR) and quantitative

  我们在本文中描述了一系列新颖的蛋白质酪氨酸磷酸酶1B（PTP1B）抑制剂逆向锥孔的设计，合成和生物学评估，这些酶在其B环的C-5位置具有一个烯丙基链。生物学筛选结果表明，这些化合物中的大多数表现出对PTP1B的抑制活性。因此，进行了初步的结构-活性关系（SAR）和定量SAR分析。在这些化合物中，有23种是最有效的抑制剂，对PTP1B的体外抑制活性最高，IC50为0.57 µM。此外，它通过激活2型糖尿病db / db小鼠的IR途径显示出显着的肝保护特性。此外，我们对接研究的结果表明，有23种作为PTP1B的特异抑制剂，有效地将WPD环从“