(1R)-2-[benzyl-[(2R)-1-(4-phenylmethoxyphenyl)propan-2-yl]amino]-1-[3,5-bis(phenylmethoxy)phenyl]ethanol | 1026184-18-8

• 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: (1R)-2-[benzyl-[(2R)-1-(4-phenylmethoxyphenyl)propan-2-yl]amino]-1-[3,5-bis(phenylmethoxy)phenyl]ethanol
• CAS: 1026184-18-8
• 化学式: C₄₅H₄₅NO₄
• 分子量: 663.857
• InChiKey: CYMKAMITANZWOJ-IVVILSPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  50
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R)-2-[benzyl-[(2R)-1-(4-phenylmethoxyphenyl)propan-2-yl]amino]-1-[3,5-bis(phenylmethoxy)phenyl]ethanol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 (R,R)-(-)-Fenoterol
  参考文献：
  名称：

  Comparative Molecular Field Analysis of the Binding of the Stereoisomers of Fenoterol and Fenoterol Derivatives to the β₂ Adrenergic Receptor

  摘要：

  Stereoisomers of fenoterol and six fenoterol derivatives have been synthesized and their binding affinities for the beta(2) adrenergic receptor (K-i beta(2)-AR), the subtype selectivity relative to the beta(1)-AR (K-i beta(1)-AR/K-i beta(2)-AR) and their functional activities were determined. Of the 26 compounds synthesized in the study, submicromolar binding affinities were observed for (R,R)-fenoterol, the (R,R)-isomer of the p-methoxy, and (R,R)- and (R,S)-isomers of 1-naphthyl derivatives and all of these compounds were active at submicromolar concentrations in cardiomyocyte contractility tests. The K-i beta(1)-AR/K-i beta(2)-AR ratios were > 40 for (R,R)-fenoterol and the (R,R)-p-methoxy and (R,S)-1-naphthyl derivatives and 14 for the (R,R)-1-napthyl derivative. The binding data was analyzed using comparative molecular field analysis (CoMFA), and the resulting model indicated that the fenoterol derivatives interacted with two separate binding sites and one steric restricted site on the pseudo-receptor and that the chirality of the second stereogenic center affected K-i beta(2) and subtype selectivity.

  DOI：

  10.1021/jm070030d
• 作为产物：
  描述：

  1-[3,5-二(苯基甲氧基)苯基]-2-溴乙烷-1-酮 在 dimethyl sulfide borane 、 (1R,2S)-1-氨基-2-茚醇 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 24.0h， 生成 (1R)-2-[benzyl-[(2R)-1-(4-phenylmethoxyphenyl)propan-2-yl]amino]-1-[3,5-bis(phenylmethoxy)phenyl]ethanol
  参考文献：
  名称：

  Comparative Molecular Field Analysis of the Binding of the Stereoisomers of Fenoterol and Fenoterol Derivatives to the β₂ Adrenergic Receptor

  摘要：

  Stereoisomers of fenoterol and six fenoterol derivatives have been synthesized and their binding affinities for the beta(2) adrenergic receptor (K-i beta(2)-AR), the subtype selectivity relative to the beta(1)-AR (K-i beta(1)-AR/K-i beta(2)-AR) and their functional activities were determined. Of the 26 compounds synthesized in the study, submicromolar binding affinities were observed for (R,R)-fenoterol, the (R,R)-isomer of the p-methoxy, and (R,R)- and (R,S)-isomers of 1-naphthyl derivatives and all of these compounds were active at submicromolar concentrations in cardiomyocyte contractility tests. The K-i beta(1)-AR/K-i beta(2)-AR ratios were > 40 for (R,R)-fenoterol and the (R,R)-p-methoxy and (R,S)-1-naphthyl derivatives and 14 for the (R,R)-1-napthyl derivative. The binding data was analyzed using comparative molecular field analysis (CoMFA), and the resulting model indicated that the fenoterol derivatives interacted with two separate binding sites and one steric restricted site on the pseudo-receptor and that the chirality of the second stereogenic center affected K-i beta(2) and subtype selectivity.

  DOI：

  10.1021/jm070030d

文献信息

• [EN] METHODS OF REGULATING CANNABINOID RECEPTOR ACTIVITY-RELATED DISORDERS AND DISEASES<br/>[FR] PROCÉDÉS DE RÉGULATION DE TROUBLES ET MALADIES ASSOCIÉS À UNE ACTIVITÉ DE RÉCEPTEUR CANNABINOÏDE
  申请人：US HEALTH

  公开号：WO2013177418A1

  公开（公告）日：2013-11-28

  This disclosure concerns the discovery of the use of fenoterol analogues for regulating cannabinoid (CB) receptor activity-related disorders and disease, such as dysregulated CB receptors, including treating a disorder or disease, such as a glioblastoma, hepatocellular carcinoma, liver cancer, colon cancer, and/or lung cancer, which is associated with altered cannabinoid receptor activity. In one example, the method includes administering to a subject having or at risk of developing a disorder or disease regulated by CB receptor activity an effective amount of a fenoterol analogue to reduce one or more symptoms associated with the disorder or disease regulated by CB receptor activity.

  本披露涉及发现使用芬特罗类似物来调节与大麻素（CB）受体活性相关的疾病和疾病，如失调的CB受体，包括治疗与改变的大麻素受体活性相关的疾病或疾病，例如胶质母细胞瘤，肝细胞癌，肝癌，结肠癌和/或肺癌。在一个例子中，该方法包括向具有或有发展CB受体活性调节的疾病或疾病的主体施用有效量的芬特罗类似物，以减少与CB受体活性调节的疾病或疾病相关的一个或多个症状。