N-(4-chlorobenzyl)-N'-cyclohexylthiourea | 345302-92-3

• 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: N-(4-chlorobenzyl)-N'-cyclohexylthiourea
• 英文别名: 1-(4-chlorobenzyl)-3-cyclohexylthiourea；1-[(4-Chlorophenyl)methyl]-3-cyclohexylthiourea
• CAS: 345302-92-3
• 化学式: C₁₄H₁₉ClN₂S
• mdl: MFCD02335767
• 分子量: 282.837
• InChiKey: XRVFNSGNRHTPDJ-UHFFFAOYSA-N

物化性质

• 熔点：
  115.5-116 °C
• 沸点：
  401.6±47.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  溴丙烷 、 N-(4-chlorobenzyl)-N'-cyclohexylthiourea 以 乙醇 为溶剂， 反应 48.0h， 以43%的产率得到[N-(4-chlorobenzyl)-N'-cyclohexyl-S-propyl]isothiourea hydrobromide
  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：

  异氰环已烷 、 对氯苄胺 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 反应 1.0h， 以77%的产率得到N-(4-chlorobenzyl)-N'-cyclohexylthiourea
  参考文献：
  名称：

  异氰化物，脂肪胺和元素硫之间的三组分反应：温和条件下完全硫原子经济的硫脲的制备

  摘要：

  摘要 发现在元素硫存在下，异氰化物与脂肪胺的反应在室温或接近室温的条件下有效进行，以极好的收率和完全的原子经济性生产硫脲。 发现在元素硫存在下，异氰化物与脂肪胺的反应在室温或接近室温的条件下有效进行，以极好的收率和完全的原子经济性生产硫脲。

  DOI：

  10.1055/s-0034-1379327

文献信息

• Molecular Determinants of Ligand Binding Modes in the Histamine H₄ Receptor: Linking Ligand-Based Three-Dimensional Quantitative Structure–Activity Relationship (3D-QSAR) Models to in Silico Guided Receptor Mutagenesis Studies
  作者：Enade P. Istyastono、Saskia Nijmeijer、Herman D. Lim、Andrea van de Stolpe、Luc Roumen、Albert J. Kooistra、Henry F. Vischer、Iwan J. P. de Esch、Rob Leurs、Chris de Graaf

  DOI：10.1021/jm201042n

  日期：2011.12.8

  pharmacophore features in H4R and its ligands, different alternative ligand binding mode hypotheses have been proposed. The current study focuses on the elucidation of the molecular determinants of H4R–ligand binding modes by combining (3D) quantitative structure–activity relationship (QSAR), protein homology modeling, molecular dynamics simulations, and site-directed mutagenesis studies. We have designed

  组胺H 4受体（H 4 R）是一种G蛋白偶联受体（GPCR），在炎症中起重要作用。与同源组胺H 3受体（H 3 R）相似，H 4 R结合口袋中的两个酸性残基D 3.32和E 5.46充当H 4 R配体中可正电离的氢键供体的必要氢键受体。考虑到这些互补药效基团特征在H 4 R及其配体中的对称分布，提出了不同的替代配体结合模式假说。当前的研究集中在阐明H 4的分子决定因素通过结合（3D）定量结构-活性关系（QSAR），蛋白质同源性建模，分子动力学模拟和定点诱变研究，实现R-配体结合模式。我们设计并合成了一系列clobenpropit（N-（4-氯苄基）-S- [3-（4（5）-咪唑基）丙基]异硫脲）衍生物，以研究H 4 R-配体相互作用和配体结合方向。有趣的是，我们的研究表明clobenpropit（2）本身可以以两种不同的结合模式结合H 4 R，而在clobenpropit isothiou
• Three-Component Reaction between Isocyanides, Aliphatic Amines and Elemental Sulfur: Preparation of Thioureas under Mild Conditions with Complete­ Atom Economy
  作者：Thanh Nguyen、Ali Al-Mourabit、Ludmila Ermolenko

  DOI：10.1055/s-0034-1379327

  日期：——

  Abstract The reaction of isocyanides with aliphatic amines in the presence of elemental sulfur was found to proceed efficiently at, or near, room temperature to produce thioureas in excellent yields and with complete atom economy. The reaction of isocyanides with aliphatic amines in the presence of elemental sulfur was found to proceed efficiently at, or near, room temperature to produce thioureas in excellent

  摘要 发现在元素硫存在下，异氰化物与脂肪胺的反应在室温或接近室温的条件下有效进行，以极好的收率和完全的原子经济性生产硫脲。 发现在元素硫存在下，异氰化物与脂肪胺的反应在室温或接近室温的条件下有效进行，以极好的收率和完全的原子经济性生产硫脲。
• 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.