(R)-(-)-1-phenyl-2-benzylaminopropane | 40816-61-3

• 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: (R)-(-)-1-phenyl-2-benzylaminopropane
• 英文别名: N-Benzylamphetamine；(2R)-N-benzyl-1-phenylpropan-2-amine
• CAS: 40816-61-3
• 化学式: C₁₆H₁₉N
• 分子量: 225.334
• InChiKey: JLCDKDGHTWGGQM-CQSZACIVSA-N

物化性质

• 沸点：
  339.0±11.0 °C(Predicted)
• 密度：
  1.000±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-(-)-1-phenyl-2-benzylaminopropane 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 120.0 ℃ 、344.75 kPa 条件下， 反应 44.0h， 生成 (R,R)-5-[1-hydroxy-2-(1-methyl-2-phenylethylamino)ethyl]-1,3-benzenediol
  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：

  苯基丙酮 在 (S)-(+)-扁桃酸 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (R)-(-)-1-phenyl-2-benzylaminopropane
  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

• PREPARATION OF (R,R)-FENOTEROL AND (R,R)-OR (R,S)-FENOTEROL ANALOGUES AND THEIR USE IN TREATING CONGESTIVE HEART FAILURE
  申请人：Wainer Irving W.

  公开号：US20120157543A1

  公开（公告）日：2012-06-21

  This disclosure concerns the discovery of (R,R)- and (R,S)-fenoterol analogues which are highly effective at binding β2-adrenergic receptors. Exemplary chemical structures for these analogues are provided. Also provided are pharmaceutical compositions including the disclosed (R,R)-fenoterol and fenoterol analogues, and methods of using such compounds and compositions for the treatment of cardiac disorders such as congestive heart failure and pulmonary disorders such as asthma or chronic obstructive pulmonary disease.

  本公开涉及(R,R)-和(R,S)-芬特罗类似物的发现，它们在结合β2-肾上腺素受体方面具有高度有效性。提供了这些类似物的示例化学结构。还提供了包括所披露的(R,R)-芬特罗和芬特罗类似物的制药组合物，以及使用这些化合物和组合物治疗心脏疾病，如充血性心力衰竭和肺部疾病，如哮喘或慢性阻塞性肺疾病的方法。
• THE USE OF FENOTEROL AND FENOTEROL ANALOGUES IN THE TREATMENT OF GLIOBLASTOMAS AND ASTROCYTOMAS
  申请人：Wainer Irving W.

  公开号：US20130005799A1

  公开（公告）日：2013-01-03

  This disclosure concerns the discovery of the use of fenoterol and (R,R)- and (R,S)-fenoterol analogues for the treatment of a tumor expressing a β2-adrenergic receptor, such as a primary brain tumor, including a glioblastoma or astrocytoma expressing a β2-adrenergic receptor. In one example, the method includes administering to a subject a therapeutically effective amount of fenoterol, a specific fenoterol analogue or a combination thereof to reduce one or more symptoms associated with the tumor, thereby treating the tumor in the subject.

  此披露涉及使用费诺特罗及(R,R)-和(R,S)-费诺特罗类似物治疗表达β2-肾上腺素能受体的肿瘤，例如表达β2-肾上腺素能受体的原发性脑肿瘤，包括胶质母细胞瘤或星形细胞瘤。在一个例子中，该方法包括向受试者施用治疗有效量的费诺特罗、特定的费诺特罗类似物或其组合物，以减轻与肿瘤相关的一个或多个症状，从而治疗受试者的肿瘤。
• Preparation of (R,R)-fenoterol and (R,R)-or (R,S)-fenoterol analogues and their use in treating congestive heart failure
  申请人：Wainer Irving W.

  公开号：US08703826B2

  公开（公告）日：2014-04-22

  This disclosure concerns the discovery of (R,R)- and (R,S)-fenoterol analogues which are highly effective at binding β2-adrenergic receptors. Exemplary chemical structures for these analogues are provided. Also provided are pharmaceutical compositions including the disclosed (R,R)-fenoterol and fenoterol analogues, and methods of using such compounds and compositions for the treatment of cardiac disorders such as congestive heart failure and pulmonary disorders such as asthma or chronic obstructive pulmonary disease.

  本公开涉及发现(R,R)-和(R,S)-芬特罗类似物，其在结合β2-肾上腺素能受体方面具有高度的效果。提供了这些类似物的示例化学结构。还提供了包括公开的(R,R)-芬特罗和芬特罗类似物的制药组合物，以及使用这些化合物和组合物治疗心脏疾病（如充血性心力衰竭）和肺部疾病（如哮喘或慢性阻塞性肺疾病）的方法。
• Use of fenoterol and fenoterol analogues in the treatment of glioblastomas and astrocytomas
  申请人：The United States of America, as represented by the Secretary, Department of Health and Human Services

  公开号：US10130594B2

  公开（公告）日：2018-11-20

  This disclosure concerns the discovery of the use of fenoterol and (R,R)- and (R,S)-fenoterol analogs for the treatment of a tumor expressing a β2-adrenergic receptor, such as a primary brain tumor, including a glioblastoma or astrocytoma expressing a β2-adrenergic receptor. In one example, the method includes administering to a subject a therapeutically effective amount of fenoterol, a specific fenoterol analog or a combination thereof to reduce one or more symptoms associated with the tumor, thereby treating the tumor in the subject.

  本公开涉及发现非诺特罗及(R,R)-和(R,S)-非诺特罗类似物用于治疗表达β2-肾上腺素能受体的肿瘤，如原发性脑肿瘤，包括表达β2-肾上腺素能受体的胶质母细胞瘤或星形细胞瘤。在一个例子中，该方法包括向受试者施用治疗有效量的非诺特罗、特异性非诺特罗类似物或其组合，以减轻与肿瘤相关的一种或多种症状，从而治疗受试者的肿瘤。
• Preparation of (R,R)-fenoterol and (R,R)- or (R,S)-fenoterol analogues and their use in treating congestive heart failure
  申请人：The United States of America, as represented by the Secretary, Department of Health and Human Services

  公开号：US10308591B2

  公开（公告）日：2019-06-04

  This disclosure concerns the discovery of (R,R)- and (R,S)-fenoterol analogs which are highly effective at binding β2-adrenergic receptors. Exemplary chemical structures for these analogs are provided. Also provided are pharmaceutical compositions including the disclosed (R,R)-fenoterol and fenoterol analogs, and methods of using such compounds and compositions for the treatment of cardiac disorders such as congestive heart failure and pulmonary disorders such as asthma or chronic obstructive pulmonary disease.

  本公开涉及(R,R)-和(R,S)-非诺特罗类似物的发现，这些类似物能非常有效地结合β2-肾上腺素能受体。本文提供了这些类似物的示例性化学结构。还提供了包括所公开的(R,R)-非诺特罗和非诺特罗类似物的药物组合物，以及使用此类化合物和组合物治疗充血性心力衰竭等心脏疾病和哮喘或慢性阻塞性肺病等肺部疾病的方法。