4-chloro-2-(4-chlorophenylcarbamoyl)phenyl undecylcarbamate | 1219818-86-6

• 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: 4-chloro-2-(4-chlorophenylcarbamoyl)phenyl undecylcarbamate
• 英文别名: [4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl] N-undecylcarbamate
• CAS: 1219818-86-6
• 化学式: C₂₅H₃₂Cl₂N₂O₃
• 分子量: 479.447
• InChiKey: UVMDTAATHCSZLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-氯代水杨酸 在 三乙胺 、 三氯化磷 作用下， 以 氯苯 、 乙腈 为溶剂， 生成 4-chloro-2-(4-chlorophenylcarbamoyl)phenyl undecylcarbamate
  参考文献：
  名称：

  Acetylcholinesterase-Inhibiting Activity of Salicylanilide N-Alkylcarbamates and Their Molecular Docking

  摘要：

  研究了一系列二十五种新型水杨酰苯胺N-烷基氨基甲酸酯作为潜在的乙酰胆碱酯酶抑制剂。这些化合物被测试了其抑制电鳗（Electrophorus electricus L.）乙酰胆碱酯酶（AChE）的能力。实验测定了它们的亲脂性，并讨论了结构-活性关系。通过分子对接研究了它们在AChE活性部位的结合模式。所有讨论的化合物都表现出比利伐斯明显著更高的AChE抑制活性，略低于加兰他敏。在苯胺环的C'(3,4)位上通过氯进行二取代，以及氨基甲酸酯部分中己基-十一烷基链的最佳长度，提供了最活性的AChE抑制剂。在C'(4)位上的单氯取代表现出比C'(3)位上稍有效的AChE抑制剂。一般来说，可以认为具有较高亲脂性的化合物表现出更高的抑制作用，化合物的活性强烈依赖于N-烷基链的长度。

  DOI：

  10.3390/molecules170910142

文献信息

• Photosynthesis—Inhibiting efficiency of 4-chloro-2-(chlorophenylcarbamoyl)phenyl alkylcarbamates
  作者：Ales Imramovsky、Matus Pesko、Juana Monreal Ferriz、Katarina Kralova、Jarmila Vinsova、Josef Jampilek

  DOI：10.1016/j.bmcl.2011.05.118

  日期：2011.8

  A series of photosynthetic electron transport (PET) inhibitors from the group of salicylanilide alkylcarbamates was investigated. The compounds were analyzed using RP-HPLC to determine lipophilicity, and their PET inhibition was determined in spinach (Spinacia oleracea L.) chloroplasts. The site of action of the studied compounds is situated at the donor site of photosystem 2 (PS 2). Compounds substituted by chlorine in C'-3 and C'-4 of the aniline ring and the optimal length of the alkyl chain pentyl-heptyl in the carbamate moiety provided the most active PET inhibitors (IC50 inhibition <10 mu mol/L). Disubstitution in C'-3,4 by chlorine caused significant PET inhibiting activity decrease. Nevertheless, for all three series of C'-3, C'-4, C'-3,4 compounds, the dependence of PET activity on lipophilicity showed to be quasi-parabolic. (C) 2011 Elsevier Ltd. All rights reserved.
• Acetylcholinesterase-Inhibiting Activity of Salicylanilide N-Alkylcarbamates and Their Molecular Docking
  作者：Ales Imramovsky、Sarka Stepankova、Jan Vanco、Karel Pauk、Juana Monreal-Ferriz、Jarmila Vinsova、Josef Jampilek

  DOI：10.3390/molecules170910142

  日期：——

  A series of twenty-five novel salicylanilide N-alkylcarbamates were investigated as potential acetylcholinesterase inhibitors. The compounds were tested for their ability to inhibit acetylcholinesterase (AChE) from electric eel (Electrophorus electricus L.). Experimental lipophilicity was determined, and the structure-activity relationships are discussed. The mode of binding in the active site of AChE was investigated by molecular docking. All the discussed compounds expressed significantly higher AChE inhibitory activity than rivastigmine and slightly lower than galanthamine. Disubstitution by chlorine in C'(3,4) of the aniline ring and the optimal length of hexyl-undecyl alkyl chains in the carbamate moiety provided the most active AChE inhibitors. Monochlorination in C'(4) exhibited slightly more effective AChE inhibitors than in C'(3). Generally it can be stated that compounds with higher lipophilicity showed higher inhibition, and the activity of the compounds is strongly dependent on the length of the N-alkyl chain.

  研究了一系列二十五种新型水杨酰苯胺N-烷基氨基甲酸酯作为潜在的乙酰胆碱酯酶抑制剂。这些化合物被测试了其抑制电鳗（Electrophorus electricus L.）乙酰胆碱酯酶（AChE）的能力。实验测定了它们的亲脂性，并讨论了结构-活性关系。通过分子对接研究了它们在AChE活性部位的结合模式。所有讨论的化合物都表现出比利伐斯明显著更高的AChE抑制活性，略低于加兰他敏。在苯胺环的C'(3,4)位上通过氯进行二取代，以及氨基甲酸酯部分中己基-十一烷基链的最佳长度，提供了最活性的AChE抑制剂。在C'(4)位上的单氯取代表现出比C'(3)位上稍有效的AChE抑制剂。一般来说，可以认为具有较高亲脂性的化合物表现出更高的抑制作用，化合物的活性强烈依赖于N-烷基链的长度。