4-benzyloxy-1-naphthoic acid chloride | 136593-80-1

• 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 chloride
• 英文别名: 4-(phenylmethoxy)naphthalenecarbonyl chloride；4-Benzyloxy-1-naphthoic acid chloride；4-phenylmethoxynaphthalene-1-carbonyl chloride
• CAS: 136593-80-1
• 化学式: C₁₈H₁₃ClO₂
• 分子量: 296.753
• InChiKey: SDJFEICDNFXJCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-1-naphthoic acid chloride 在 palladium on activated charcoal 、 ammonium formate 、 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate 作用下， 反应 1.0h， 生成 (4-Hydroxy-naphthalen-1-yl)-[1-(1-methyl-piperidin-2-ylmethyl)-1H-indol-3-yl]-methanone
  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：

  1-溴-4-苯基甲氧基萘 在 正丁基锂 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 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

文献信息

• ISOINDOLE DERIVATIVES USEFUL FOR TREATING PAIN, GASTROINTESTINAL DISEASES AND CANCER
  申请人：AstraZeneca AB

  公开号：EP2029535A1

  公开（公告）日：2009-03-04
• [EN] ISOINDOLE DERIVATIVES USEFUL FOR TREATING PAIN, GASTROINTESTINAL DISEASES AND CANCER<br/>[FR] DÉRIVÉS D'ISOINDOLE UTILISÉS POUR TRAITER LA DOULEUR, LES MALADIES DU TUBE DIGESTIF ET LE CANCER
  申请人：ASTRAZENECA AB

  公开号：WO2007139464A1

  公开（公告）日：2007-12-06

  [EN] Compounds of formula I or pharmaceutically acceptable salts thereof: [Chemical formula should be inserted here. Please see paper copy] I wherein X, R₁, R₂, R₃, m and n are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.
  [FR] L'invention concerne des composés de formule (I) ou leurs sels pharmaceutiquement acceptables. Dans cette formule, X, R₁, R₂, R₃, m and n sont spécifiés dans la description, de même que la préparation des sels et des compositions pharmaceutiques contenant lesdits composés. Les composés de l'invention sont utilisés dans le cadre d'une thérapie, en particulier dans la gestion de la douleur.