2-(4-aminophenoxy)-N-(4-chlorophenyl)acetamide | 881607-14-3

• 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: 2-(4-aminophenoxy)-N-(4-chlorophenyl)acetamide
• CAS: 881607-14-3
• 化学式: C₁₄H₁₃ClN₂O₂
• mdl: MFCD06662308
• 分子量: 276.722
• InChiKey: NSZOTDJQIOUVRN-UHFFFAOYSA-N

物化性质

• 熔点：
  195-196 °C
• 沸点：
  537.7±40.0 °C(Predicted)
• 密度：
  1.348±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-aminophenoxy)-N-(4-chlorophenyl)acetamide 在 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 水 为溶剂， 反应 15.0h， 生成 5-(6-{4-[(4-chloro-phenylcarbamoyl)-methoxy]-phenylamino}-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid ethylamide
  参考文献：
  名称：

  N6-[(Hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5′-N-ethylcarboxamido-adenosines: The first example of adenosine-related structures with potent agonist activity at the human A2B adenosine receptor

  摘要：

  A new series of N-6-[(hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5'-N-ethylcarboxamido-adenosines (24-43) has been synthesised and tested in binding assays at hA(1), hA(2A) and hA(3) adenosine receptors, and in a functional assay at the hA(2B) subtype. The examined compounds displayed high potency in activating A(2B) receptors with good selectivity versus A(2A) subtypes. The introduction of an unsubstituted 4-[(phenylcarbamoyl)-methoxyl-phenyI chain at the N-6 position of 5'-N-ethylcarboxamido -adenosine led us to the recognition of compound 24 as a full agonist displaying the highest efficacy of the series (EC50 hA(2B) = 7.3 nM). These compounds represent the first report about adenosine-related structures capable of activating hA2B subtype in the low nanomolar range. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.055
• 作为产物：
  描述：

  N-(4-氯苯基)-2-氯乙酰胺 在 palladium on activated charcoal sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 12.0h， 生成 2-(4-aminophenoxy)-N-(4-chlorophenyl)acetamide
  参考文献：
  名称：

  N6-[(Hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5′-N-ethylcarboxamido-adenosines: The first example of adenosine-related structures with potent agonist activity at the human A2B adenosine receptor

  摘要：

  A new series of N-6-[(hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5'-N-ethylcarboxamido-adenosines (24-43) has been synthesised and tested in binding assays at hA(1), hA(2A) and hA(3) adenosine receptors, and in a functional assay at the hA(2B) subtype. The examined compounds displayed high potency in activating A(2B) receptors with good selectivity versus A(2A) subtypes. The introduction of an unsubstituted 4-[(phenylcarbamoyl)-methoxyl-phenyI chain at the N-6 position of 5'-N-ethylcarboxamido -adenosine led us to the recognition of compound 24 as a full agonist displaying the highest efficacy of the series (EC50 hA(2B) = 7.3 nM). These compounds represent the first report about adenosine-related structures capable of activating hA2B subtype in the low nanomolar range. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.055

文献信息

• Novel Quinazoline Derivatives Bearing Various 4-Aniline Moieties as Potent EGFR Inhibitors with Enhanced Activity Against NSCLC Cell Lines
  作者：Changyan Wang、Yajun Sun、Xingqi Zhu、Bin Wu、Qiao Wang、Yuhong Zhen、Xiaohong Shu、Kexin Liu、Youwen Zhou、Xiaodong Ma

  DOI：10.1111/cbdd.12692

  日期：2016.4

  the EGFR wild‐type A431 cells and 5c with an IC50 of 0.001 μm against the gefitinib‐sensitive HCC827 cells (EGFR del E746‐A750) was identified as highly active EGFR inhibitors. It was also significant that the discovered analogue 2f, not only has high potency against the gefitinib‐sensitive cells (IC50 = 0.031 μm), but also possesses remarkably improved activity against the gefitinib‐resistant cells

  合成了一类带有各种C-4苯胺部分的新型喹唑啉衍生物，并对其进行了生物学评估，认为它们是有效的表皮生长因子受体（EGFR）抑制剂，可用于治疗非小细胞肺癌（NSCLC）。这些抑制剂中的大多数在抑制这些癌细胞系方面与吉非替尼相当，其中一些甚至表现出优异的抑制活性。特别地，模拟图5b与IC 50 0.10 μ米针对EGFR野生型A431细胞和5c中有一个IC 50 0.001的μ米对吉非替尼敏感的HCC827细胞（EGFR del E746‐A750）的抗性被确定为高活性EGFR抑制剂。它也是显著所发现的类似物2F，不仅具有对吉非替尼敏感性细胞的高效力（IC 50 = 0.031 μ米），但也具有显着的对抗吉非替尼抗性细胞改善的活性。另外，用于评估典型抑制剂作用的酶促测定和蛋白质印迹分析表明，这些分子强烈干扰EGFR靶标。
• N6-[(Hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5′-N-ethylcarboxamido-adenosines: The first example of adenosine-related structures with potent agonist activity at the human A2B adenosine receptor
  作者：Pier Giovanni Baraldi、Delia Preti、Mojgan Aghazadeh Tabrizi、Francesca Fruttarolo、Giulia Saponaro、Stefania Baraldi、Romeo Romagnoli、Allan R. Moorman、Stefania Gessi、Katia Varani、Pier Andrea Borea

  DOI：10.1016/j.bmc.2007.01.055

  日期：2007.4

  A new series of N-6-[(hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5'-N-ethylcarboxamido-adenosines (24-43) has been synthesised and tested in binding assays at hA(1), hA(2A) and hA(3) adenosine receptors, and in a functional assay at the hA(2B) subtype. The examined compounds displayed high potency in activating A(2B) receptors with good selectivity versus A(2A) subtypes. The introduction of an unsubstituted 4-[(phenylcarbamoyl)-methoxyl-phenyI chain at the N-6 position of 5'-N-ethylcarboxamido -adenosine led us to the recognition of compound 24 as a full agonist displaying the highest efficacy of the series (EC50 hA(2B) = 7.3 nM). These compounds represent the first report about adenosine-related structures capable of activating hA2B subtype in the low nanomolar range. (c) 2007 Elsevier Ltd. All rights reserved.