N-(methoxycarbonyl)-9-aminonmethyl-9,10-dihydroanthracene | 425629-82-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-(methoxycarbonyl)-9-aminonmethyl-9,10-dihydroanthracene
• 英文别名: methyl N-(9,10-dihydroanthracen-9-ylmethyl)carbamate
• CAS: 425629-82-9
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: WSLYSJBWSCDURL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(methoxycarbonyl)-9-aminonmethyl-9,10-dihydroanthracene 在 硼烷四氢呋喃络合物 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 37.0h， 生成 2,3,7,11b-Tetrahydro-1H-dibenzo[de,h]isoquinoline
  参考文献：
  名称：

  Geometry−Affinity Relationships of the Selective Serotonin Receptor Ligand 9-(Aminomethyl)-9,10-dihydroanthracene

  摘要：

  With the exception of its two aromatic rings and basic nitrogen atom, 9-(aminomethyl)-9,10-dihydroanthracene (AMDA; 1) is remarkably devoid of the pharmacophore features usually associated with high-affinity receptor ligands such as the heteroatom hydrogen bonding features of the endogenous ligand serotonin. AMDA does contain a phenylethylamine skeleton within a tricyclic ring system, and the presence of the second aromatic group is necessary for optimal receptor affinity. The structural requirements for the binding of AMDA at 5-HT2A receptors were investigated with respect to the geometric relationship between the two aromatic rings. It appears that the geometry of the AMDA parent is in the optimal range for fold angle between aromatic moieties. Evaluation of conformationally constrained derivatives of AMDA suggests that a chain extended trans, gauche form is most likely responsible for high affinity.

  DOI：

  10.1021/jm010354g
• 作为产物：
  描述：

  9-Aminomethyl-9,10-dihydroanthracen 、 氯甲酸甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以67.4 %的产率得到N-(methoxycarbonyl)-9-aminonmethyl-9,10-dihydroanthracene
  参考文献：
  名称：

  [EN] COMPOUNDS AND COMPOSITIONS FOR TREATING CNS DISORDERS
  [FR] COMPOSÉS ET COMPOSITIONS POUR LE TRAITEMENT DE TROUBLES DU SYSTÈME NERVEUX CENTRAL

  摘要：

  本公开提供化合物及其制药组合物。还提供制备和使用这些化合物的方法。这些化合物可以用于调节，例如激活TAAR1，并可用于治疗、预防、诊断和/或管理各种中枢神经系统疾病。

  公开号：

  WO2022204150A1

文献信息

• [EN] COMPOUNDS AND COMPOSITIONS FOR TREATING CNS DISORDERS<br/>[FR] COMPOSÉS ET COMPOSITIONS POUR LE TRAITEMENT DE TROUBLES DU SYSTÈME NERVEUX CENTRAL
  申请人：BLUE OAK PHARMACEUTICALS INC

  公开号：WO2022204150A1

  公开（公告）日：2022-09-29

  The present disclosure provides compounds and pharmaceutical compositions thereof. Methods of making and using the compounds are also provided. The compounds can be used to modulate such as activate TAAR1 and can be used for the treatment, prevention, diagnosis and/or management of various CNS disorders.

  本公开提供化合物及其制药组合物。还提供制备和使用这些化合物的方法。这些化合物可以用于调节，例如激活TAAR1，并可用于治疗、预防、诊断和/或管理各种中枢神经系统疾病。
• Geometry−Affinity Relationships of the Selective Serotonin Receptor Ligand 9-(Aminomethyl)-9,10-dihydroanthracene
  作者：Scott P. Runyon、Srinivas Peddi、Jason E. Savage、Bryan L. Roth、Richard A. Glennon、Richard B. Westkaemper

  DOI：10.1021/jm010354g

  日期：2002.4.1

  With the exception of its two aromatic rings and basic nitrogen atom, 9-(aminomethyl)-9,10-dihydroanthracene (AMDA; 1) is remarkably devoid of the pharmacophore features usually associated with high-affinity receptor ligands such as the heteroatom hydrogen bonding features of the endogenous ligand serotonin. AMDA does contain a phenylethylamine skeleton within a tricyclic ring system, and the presence of the second aromatic group is necessary for optimal receptor affinity. The structural requirements for the binding of AMDA at 5-HT2A receptors were investigated with respect to the geometric relationship between the two aromatic rings. It appears that the geometry of the AMDA parent is in the optimal range for fold angle between aromatic moieties. Evaluation of conformationally constrained derivatives of AMDA suggests that a chain extended trans, gauche form is most likely responsible for high affinity.