2-[4-(acetylamino)phenyl]ethyl chloride | 52273-67-3

• 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-(acetylamino)phenyl]ethyl chloride
• 英文别名: N-[4-(2-chloro-ethyl)-phenyl]-acetamide；N-[4-(2-Chloroethyl)phenyl]acetamide；2-p-Acetamidophenylethylchlorid
• CAS: 52273-67-3
• 化学式: C₁₀H₁₂ClNO
• mdl: MFCD19304930
• 分子量: 197.664
• InChiKey: YGKNSAIBTCSDDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  117-119 °C
• 沸点：
  381.0±25.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-[4-(acetylamino)phenyl]ethyl chloride 在 盐酸 、 硫酸 、 溴 、 硝酸 、 镍 、 sodium carbonate 、 一水合肼 、 potassium iodide 作用下， 以 乙醇 、 乙酸酐 、 溶剂黄146 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 3-bromo-5-(2-dipropylamino-ethyl)-benzene-1,2-diamine
  参考文献：
  名称：

  几种新型卤代苯并咪唑类多巴胺能配体的静电表面电位计算

  摘要：

  我们检查了几种新的苯并咪唑型配体的电子密度分布（静电表面电位；ESP）对其与 D1 和 D2 多巴胺受体 (DAR) 结合亲和力的影响。从牛尾状核的突触体膜制备受体。[3H] SCH 23390 和 [3H] 螺环哌啶酮分别用作 D1 和 D2 受体的特异性放射性标记。这些化合物的 ESP 使用 Gaussian 98 W 软件计算。用已知的多巴胺能配体进行的计算表明，这些化合物的芳环中的电子密度电荷有利于 D2 DAR 的更高结合亲和力。这通过几种已知多巴胺能配体的卤化类似物的合成得到证实。卤化导致分子芳香部分的正电荷增加。新合成的化合物都不能有效地从 D1 DAR 中置换 [3H] SCH 23390。与母体化合物和溴化配体相比，将氯引入分子中导致新配体的 D2 DAR 具有更高的结合亲和力。这种差异可能源于氯原子和溴原子大小的差异，这可能影响配体与受体结合位点的相互作用。然而，在以溴

  DOI：

  10.1002/ardp.200300846
• 作为产物：
  描述：

  邻氯乙苯 在 10percent Pd/C 吡啶 、 氢气 、 硝酸 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 24.5h， 生成 2-[4-(acetylamino)phenyl]ethyl chloride
  参考文献：
  名称：

  7-Substituted 5-Amino-2-(2-furyl)pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines as A_2A Adenosine Receptor Antagonists:  A Study on the Importance of Modifications at the Side Chain on the Activity and Solubility

  摘要：

  It was demonstrated in the early 1990s that adenosine exerts many physiological functions through the interaction with four different receptors, named A(1), A(2A), A(2B), and A(3). In the past few years, our group has been involved in the development of A(2A) antagonists, which led to the synthesis of SCH 58261 (1), the first potent and selective adenosine A(2A) antagonist, which has been widely used as a reference compound. In this paper, we present an extended series of pyrazolotriazolopyrimidines synthesized with the aim to investigate the influence of the substitutions on the pyrazole ring. The choice of the substituents was based on their capability to improve water solubility while retaining high affinity and selectivity at the human A(2A) adenosine receptor subtype. In this series, some structural characteristics that are important for activity, i.e., tricyclic structure, free amino group at 5-position, furan ring, and substituent at 7-position on the pyrazole moiety, have been maintained. We focused our attention on the nature of the phenyl ring substituent to improve water solubility. Following this strategy, we developed new compounds with good affinity and selectivity for A(2A) adenosine receptors, such as 8d (K-i 0.12 nM; hA(1)/hA(2A) ratio = 1025; R-m = 2.8), 8h (K-i 0.22; hA(1)/hA(2A) ratio = 9818; R-m = 3.4), 8i (K-i 0.18 nM; hA(1)/hA(2A) ratio = 994; R-m = 2.8), 8k (K-i 0.13 nM; hA(1)/hA(2A) ratio = 4430; R-m = 3.6), and 14b (K-i 0.19 nM; hA(1)/hA(2A) ratio = 2273; R-m = 2.7). All the new synthesized compounds have no significant interaction with either-A(2B) or A(3) receptor subtypes. This new series of compounds deeply enlightens some structural requirements to display high affinity and selectivity for the A(2A) adenosine receptor subtype, although our goal of identifying new compounds with increased water solubility was not completely achieved. On this basis, other strategies will be devised to improve this class of compounds with a profile that appears to be promising for treatment of neurodegenerative disorders, such as Parkinson's disease.

  DOI：

  10.1021/jm010924c

文献信息

• Nouveaux dérivés chroméniques, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：ADIR ET COMPAGNIE

  公开号：EP0887350B1

  公开（公告）日：2001-08-22
• US6090837A
  申请人：——

  公开号：US6090837A

  公开（公告）日：2000-07-18
• US6326377B1
  申请人：——

  公开号：US6326377B1

  公开（公告）日：2001-12-04
• US6365605B1
  申请人：——

  公开号：US6365605B1

  公开（公告）日：2002-04-02
• 7-Substituted 5-Amino-2-(2-furyl)pyrazolo[4,3-<i>e</i>]-1,2,4-triazolo[1,5-<i>c</i>]pyrimidines as A_2A Adenosine Receptor Antagonists:  A Study on the Importance of Modifications at the Side Chain on the Activity and Solubility
  作者：Pier Giovanni Baraldi、Barbara Cacciari、Romeo Romagnoli、Giampiero Spalluto、Angela Monopoli、Ennio Ongini、Katia Varani、Pier Andrea Borea

  DOI：10.1021/jm010924c

  日期：2002.1.1

  It was demonstrated in the early 1990s that adenosine exerts many physiological functions through the interaction with four different receptors, named A(1), A(2A), A(2B), and A(3). In the past few years, our group has been involved in the development of A(2A) antagonists, which led to the synthesis of SCH 58261 (1), the first potent and selective adenosine A(2A) antagonist, which has been widely used as a reference compound. In this paper, we present an extended series of pyrazolotriazolopyrimidines synthesized with the aim to investigate the influence of the substitutions on the pyrazole ring. The choice of the substituents was based on their capability to improve water solubility while retaining high affinity and selectivity at the human A(2A) adenosine receptor subtype. In this series, some structural characteristics that are important for activity, i.e., tricyclic structure, free amino group at 5-position, furan ring, and substituent at 7-position on the pyrazole moiety, have been maintained. We focused our attention on the nature of the phenyl ring substituent to improve water solubility. Following this strategy, we developed new compounds with good affinity and selectivity for A(2A) adenosine receptors, such as 8d (K-i 0.12 nM; hA(1)/hA(2A) ratio = 1025; R-m = 2.8), 8h (K-i 0.22; hA(1)/hA(2A) ratio = 9818; R-m = 3.4), 8i (K-i 0.18 nM; hA(1)/hA(2A) ratio = 994; R-m = 2.8), 8k (K-i 0.13 nM; hA(1)/hA(2A) ratio = 4430; R-m = 3.6), and 14b (K-i 0.19 nM; hA(1)/hA(2A) ratio = 2273; R-m = 2.7). All the new synthesized compounds have no significant interaction with either-A(2B) or A(3) receptor subtypes. This new series of compounds deeply enlightens some structural requirements to display high affinity and selectivity for the A(2A) adenosine receptor subtype, although our goal of identifying new compounds with increased water solubility was not completely achieved. On this basis, other strategies will be devised to improve this class of compounds with a profile that appears to be promising for treatment of neurodegenerative disorders, such as Parkinson's disease.