2-(4-n-hexylphenyl)-2-hydroxy-2-phenylacetonitrile | 1075741-12-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: 2-(4-n-hexylphenyl)-2-hydroxy-2-phenylacetonitrile
• 英文别名: 2-(4-Hexylphenyl)-2-hydroxy-2-phenylacetonitrile
• CAS: 1075741-12-6
• 化学式: C₂₀H₂₃NO
• 分子量: 293.409
• InChiKey: RULBLTZNKQGTQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-n-hexylphenyl)-2-hydroxy-2-phenylacetonitrile 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 反应 2.0h， 以67%的产率得到2-(4-n-hexylphenyl)-2-phenylacetonitrile
  参考文献：
  名称：

  Potential Modes of Interaction of 9-Aminomethyl-9,10-dihydroanthracene (AMDA) Derivatives with the 5-HT_2A Receptor: A Ligand Structure-Affinity Relationship, Receptor Mutagenesis and Receptor Modeling Investigation

  摘要：

  The effects of 3-position substitution of 9-aminomethyl-9,10-dihydroanthracene (AMDA) on 5-HT2A receptor affinity were determined and compared to a parallel series of DOB-like 1-(2,5-dimethoxyphenyl)-2-aminopropanes substituted at the 4-position. The results were interpreted within the context of 5-HT2A receptor models that suggest that members of the DOB-like series call bind to the receptor in two distinct modes that correlate with the compounds' functional activity. Automated ligand docking and molecular dynamics suggest that all of the AMDA derivatives, the parent of which is a 5-HT2A antagonist, bind in a fashion analogous to that for the sterically demanding antagonist DOB-like compounds. The failure of the F340(6.52)L mutation to adversely affect the affinity of AMDA and the 3-bromo derivative is consistent with the proposed modes of orientation. Evaluation of ligand-receptor complex models suggest that a valine/threonine exchange between the 5-HT2A and D-2 receptors may be the origin of selectivity for AMDA and two substituted derivatives.

  DOI：

  10.1021/jm800771x
• 作为产物：
  描述：

  在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以0.680 g的产率得到2-(4-n-hexylphenyl)-2-hydroxy-2-phenylacetonitrile
  参考文献：
  名称：

  Potential Modes of Interaction of 9-Aminomethyl-9,10-dihydroanthracene (AMDA) Derivatives with the 5-HT_2A Receptor: A Ligand Structure-Affinity Relationship, Receptor Mutagenesis and Receptor Modeling Investigation

  摘要：

  The effects of 3-position substitution of 9-aminomethyl-9,10-dihydroanthracene (AMDA) on 5-HT2A receptor affinity were determined and compared to a parallel series of DOB-like 1-(2,5-dimethoxyphenyl)-2-aminopropanes substituted at the 4-position. The results were interpreted within the context of 5-HT2A receptor models that suggest that members of the DOB-like series call bind to the receptor in two distinct modes that correlate with the compounds' functional activity. Automated ligand docking and molecular dynamics suggest that all of the AMDA derivatives, the parent of which is a 5-HT2A antagonist, bind in a fashion analogous to that for the sterically demanding antagonist DOB-like compounds. The failure of the F340(6.52)L mutation to adversely affect the affinity of AMDA and the 3-bromo derivative is consistent with the proposed modes of orientation. Evaluation of ligand-receptor complex models suggest that a valine/threonine exchange between the 5-HT2A and D-2 receptors may be the origin of selectivity for AMDA and two substituted derivatives.

  DOI：

  10.1021/jm800771x