N-(4-chlorobenzyl)-N'-ethylthiourea | 57294-95-8

• 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: N-(4-chlorobenzyl)-N'-ethylthiourea
• 英文别名: 1-(4-Chlorobenzyl)-3-ethylthiourea；1-[(4-chlorophenyl)methyl]-3-ethylthiourea
• CAS: 57294-95-8
• 化学式: C₁₀H₁₃ClN₂S
• mdl: MFCD04208855
• 分子量: 228.746
• InChiKey: UWZZUKMOHNJNEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 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：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-chlorobenzyl)-N'-ethylthiourea 、 4-(3-bromopropyl)-1H-imidazole hydrobromide 以 乙醇 为溶剂， 反应 48.0h， 以25%的产率得到N-(4-chlorobenzyl)-N'-ethyl-S-[3-(4(5)-imidazolyl)propyl]isothiourea dihydrobromide
  参考文献：
  名称：

  Development of a Pharmacophore Model for Histamine H₃ Receptor Antagonists, Using the Newly Developed Molecular Modeling Program SLATE

  摘要：

  New molecular modeling tools were developed to construct a qualitative pharmacophore model for histamine HQ receptor antagonists. The program SLATE superposes ligands assuming optimum hydrogen bond geometry. One or two ligands are allowed to flex in the procedure, thereby enabling the determination of the bioactive conformation of flexible Hg antagonists. In the derived model, four hydrogen-bonding site points and two hydrophobic pockets available for binding antagonists are revealed. The model results in a better understanding of the structure-activity relationships of Ha antagonists. To validate the model, a series of new antagonists was synthesized. The compounds were designed to interact with all four hydrogen-bonding site points and the two hydrophobic pockets simultaneously. These ligands have high HE receptor affinity, thereby illustrating how the model can be used in the design of new classes of H-3 antagonists.

  DOI：

  10.1021/jm001109k
• 作为产物：
  描述：

  异硫氰酸乙酯 、 对氯苄胺 以 乙醚 为溶剂， 反应 2.0h， 以90%的产率得到N-(4-chlorobenzyl)-N'-ethylthiourea
  参考文献：
  名称：

  Development of a Pharmacophore Model for Histamine H₃ Receptor Antagonists, Using the Newly Developed Molecular Modeling Program SLATE

  摘要：

  New molecular modeling tools were developed to construct a qualitative pharmacophore model for histamine HQ receptor antagonists. The program SLATE superposes ligands assuming optimum hydrogen bond geometry. One or two ligands are allowed to flex in the procedure, thereby enabling the determination of the bioactive conformation of flexible Hg antagonists. In the derived model, four hydrogen-bonding site points and two hydrophobic pockets available for binding antagonists are revealed. The model results in a better understanding of the structure-activity relationships of Ha antagonists. To validate the model, a series of new antagonists was synthesized. The compounds were designed to interact with all four hydrogen-bonding site points and the two hydrophobic pockets simultaneously. These ligands have high HE receptor affinity, thereby illustrating how the model can be used in the design of new classes of H-3 antagonists.

  DOI：

  10.1021/jm001109k

文献信息

• Aminolysis of Aryl <i>N</i>-Ethyl Thionocarbamates: Cooperative Effects of Atom Pairs O and S on the Reactivity and Mechanism
  作者：Hyuck Keun Oh、Ji Young Oh、Dae Dong Sung、Ikchoon Lee

  DOI：10.1021/jo050606b

  日期：2005.7.1

  with benzylamines (XC6H4CH2NH2) in acetonitrile are investigated at 30.0 °C. The rate of ETNC is slower by a factor of ca. 3 than the corresponding aminolysis of aryl N-ethyl thiocarbamate (AETC/EtHN-(CO)-SC6H4Z), which has been interpreted in terms of cooperative effects of atom pairs O and S on the reactivity and mechanism. For concerted processes, these effects predict a rate sequence, −C(S)−S− <

  在30.0°C下研究了芳基N-乙基硫代氨基甲酸酯（ETNC / EtHN-C（S）-OC 6 H 4 Z）与苄胺（XC 6 H 4 CH 2 NH 2）的氨解反应。ETNC的速度减慢了大约两倍。与芳基N-乙基硫代氨基甲酸酯的相应氨解反应（AETC / EtHN-（C O）-SC 6 H 4 Z）相比，它的原子分解反应要比图3所示，这是根据原子对O和S对反应性和机理的协同作用来解释的。对于一致的过程，这些效应可预测速率序列-C（S）-S- <-C（S）-O- <-C-（O）-S- <-C-（O）-O-，并且当前结果与此顺序一致。负交叉相互作用常数，ρ XZ = -0.87，的幅度β Ž（= 0.36-0.50）和失败的RSP的是在与该协同机制一致。涉及氘化苄胺的正常动力学同位素效应k H / k D = 1.52-1.78表明存在氢键合的环状过渡态。还讨论了影响该机制的其他因素。
• VASSILEV G. N.; YONOVA P. A., DOKL. BOLG. AN. <DVAN-AD>, 1975, 28, NO 7, 931-933
  作者：VASSILEV G. N.、 YONOVA P. A.

  DOI：——

  日期：——
• Development of a Pharmacophore Model for Histamine H₃ Receptor Antagonists, Using the Newly Developed Molecular Modeling Program SLATE
  作者：Iwan J. P. De Esch、James E. J. Mills、Tim D. J. Perkins、Giuseppe Romeo、Marcel Hoffmann、Kerstin Wieland、Rob Leurs、Wiro M. P. B. Menge、Paul H. J. Nederkoorn、Philip M. Dean、Henk Timmerman

  DOI：10.1021/jm001109k

  日期：2001.5.1

  New molecular modeling tools were developed to construct a qualitative pharmacophore model for histamine HQ receptor antagonists. The program SLATE superposes ligands assuming optimum hydrogen bond geometry. One or two ligands are allowed to flex in the procedure, thereby enabling the determination of the bioactive conformation of flexible Hg antagonists. In the derived model, four hydrogen-bonding site points and two hydrophobic pockets available for binding antagonists are revealed. The model results in a better understanding of the structure-activity relationships of Ha antagonists. To validate the model, a series of new antagonists was synthesized. The compounds were designed to interact with all four hydrogen-bonding site points and the two hydrophobic pockets simultaneously. These ligands have high HE receptor affinity, thereby illustrating how the model can be used in the design of new classes of H-3 antagonists.