4-benzyloxy-1-naphthoic acid | 87344-63-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-benzyloxy-1-naphthoic acid
• 英文别名: 4-benzyloxy-[1]naphthoic acid；4-Benzyloxy-[1]naphthoesaeure；4-(Phenylmethoxy)-1-naphthalenecarboxylic acid；4-phenylmethoxynaphthalene-1-carboxylic acid
• CAS: 87344-63-6
• 化学式: C₁₈H₁₄O₃
• 分子量: 278.307
• InChiKey: JMTFAIVHIUNGRO-UHFFFAOYSA-N

物化性质

• 沸点：
  487.6±20.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-1-naphthoic acid 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 反应 2.0h， 生成 4-benzyloxy-1-naphthoic acid chloride
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of a Novel Series of Aminoalkylindoles with Potential for Imaging the Neuronal Cannabinoid Receptor by Positron Emission Tomography

  摘要：

  A new series of CB1 ligands with high binding affinity (K-i = 0.7-100 nM) and moderate lipophilicity (cLogD(7.4)) in the range of 2.1-4.5 has been synthesized. A structure-activity relationship study demonstrated that for the studied set of aminoalkylindoles, the molecular dipole of the ground state conformation within the series was inversely related to the affinity. The racemic ligand with highest affinity (0.7 nM), 3-(4-fluoronaphthoyl)-1-(N-methylpiperidin-2-ylmethyl)indole, was radiolabeled with F-18. This radioligand specifically labeled CB, receptors in mouse brain and accumulated in regions of high versus low CB1 receptor density in a ratio of 1.6. The displaceable radioactivity of one enantiomer in the brains of mice determined in a pretreatment study using the CB, antagonist N-(piperidinyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716) was nearly double that of the racemate for the same determination; therefore, the active enantiomer is a candidate for PET studies in animals. A pretreatement study for the other enantiomer found no displaceable radioactivity in the same group of mice; this result suggested the enantiomer was inactive.

  DOI：

  10.1021/jm0502743
• 作为产物：
  描述：

  4-(benzyloxy)-1-naphthaldehyde 在 sodium hydroxide 、 silver(l) oxide 作用下， 生成 4-benzyloxy-1-naphthoic acid
  参考文献：
  名称：

  696.羟基萘甲酸酯系列。第一部分。4-羟基萘甲酸及其简单酯的合成

  摘要：

  DOI：

  10.1039/jr9520003634

文献信息

• Synthesis and Structure−Activity Relationship of a Novel Series of Aminoalkylindoles with Potential for Imaging the Neuronal Cannabinoid Receptor by Positron Emission Tomography
  作者：Peter G. Willis、Olga A. Pavlova、Svetlana I. Chefer、D. Bruce Vaupel、Alexey G. Mukhin、Andrew G. Horti

  DOI：10.1021/jm0502743

  日期：2005.9.1

  A new series of CB1 ligands with high binding affinity (K-i = 0.7-100 nM) and moderate lipophilicity (cLogD(7.4)) in the range of 2.1-4.5 has been synthesized. A structure-activity relationship study demonstrated that for the studied set of aminoalkylindoles, the molecular dipole of the ground state conformation within the series was inversely related to the affinity. The racemic ligand with highest affinity (0.7 nM), 3-(4-fluoronaphthoyl)-1-(N-methylpiperidin-2-ylmethyl)indole, was radiolabeled with F-18. This radioligand specifically labeled CB, receptors in mouse brain and accumulated in regions of high versus low CB1 receptor density in a ratio of 1.6. The displaceable radioactivity of one enantiomer in the brains of mice determined in a pretreatment study using the CB, antagonist N-(piperidinyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716) was nearly double that of the racemate for the same determination; therefore, the active enantiomer is a candidate for PET studies in animals. A pretreatement study for the other enantiomer found no displaceable radioactivity in the same group of mice; this result suggested the enantiomer was inactive.
• 696. The hydroxynaphthoate series. Part I. A synthesis of 4-hydroxynaphthoic acid and its simple esters
  作者：G. W. K. Cavill、J. R. Tetaz

  DOI：10.1039/jr9520003634

  日期：——