2-溴-1-(3,5-二(苄氧基)苯基)乙醇 | 103145-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-溴-1-(3,5-二(苄氧基)苯基)乙醇
• 英文名称: (S)-(+)-3',5'-dibenzyloxyphenylbromohydrin
• 英文别名: (1S)-1-[3,5-bis(phenylmethoxy)phenyl]-2-bromoethanol
• CAS: 103145-39-7
• 化学式: C₂₂H₂₁BrO₃
• 分子量: 413.311
• InChiKey: KNEIXCFXUQTJQL-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-溴-1-(3,5-二(苄氧基)苯基)乙醇 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 22.0h， 生成 (1S)-2-[benzyl-[(2R)-heptan-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
• 作为产物：
  描述：

  3,5-二苄氧基苯乙酮 在 三氟化硼乙醚 、 溴 、 (1S,2R)-(-)-1-氨基-2-茚醇 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 为溶剂， 反应 4.5h， 生成 2-溴-1-(3,5-二(苄氧基)苯基)乙醇
  参考文献：
  名称：

  Use of fenoterol and fenoterol analogues in the treatment of glioblastomas and astrocytomas

  摘要：

  这项披露涉及发现使用非托罗尔和(R,R)-和(R,S)-非托罗尔类似物治疗表达β2肾上腺素受体的肿瘤，例如表达β2肾上腺素受体的原发性脑肿瘤，包括表达β2肾上腺素受体的胶质母细胞瘤或星形细胞瘤。在一个示例中，该方法包括向受试者施用治疗有效量的非托罗尔、特定的非托罗尔类似物或其组合，以减少与肿瘤相关的一个或多个症状，从而治疗受试者的肿瘤。

  公开号：

  US09492405B2

文献信息

• Use of fenoterol and fenoterol analogues in the treatment of glioblastomas and astrocytomas
  申请人：Wainer Irving W.

  公开号：US09492405B2

  公开（公告）日：2016-11-15

  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.

  这项披露涉及发现使用非托罗尔和(R,R)-和(R,S)-非托罗尔类似物治疗表达β2肾上腺素受体的肿瘤，例如表达β2肾上腺素受体的原发性脑肿瘤，包括表达β2肾上腺素受体的胶质母细胞瘤或星形细胞瘤。在一个示例中，该方法包括向受试者施用治疗有效量的非托罗尔、特定的非托罗尔类似物或其组合，以减少与肿瘤相关的一个或多个症状，从而治疗受试者的肿瘤。
• Asymmetric Transfer Hydrogenation of Ketones Catalyzed by Hydrophobic Metal−Amido Complexes in Aqueous Micelles and Vesicles
  作者：Fei Wang、Hui Liu、Linfeng Cun、Jin Zhu、Jingen Deng、Yaozhong Jiang

  DOI：10.1021/jo0514826

  日期：2005.11.1

  Asymmetric transfer hydrogenation of ketones, especially (X-bromomethyl aromatic ketones, catalyzed by unmodified, hydrophobic transition metal-amido complexes (TsDPEN-M), was performed successfully with significant enhancement of activity, chemoselectivity, and enantioselectivity (up to 99% ee) in aqueous media containing micelles and vesicles. The hydrophobic catalyst, embedded in micelles constructed from the surfactant cetyltrimethylammonium bromide (CTAB), could be separated from the organic phase along with the products and was recycled for at least six times.
• Comparative Molecular Field Analysis of the Binding of the Stereoisomers of Fenoterol and Fenoterol Derivatives to the β₂ Adrenergic Receptor
  作者：Krzysztof Jozwiak、Chakir Khalid、Mary J. Tanga、Ilona Berzetei-Gurske、Lucita Jimenez、Joseph A. Kozocas、Anthony Woo、Weizhong Zhu、Rui-Ping Xiao、Darrell R. Abernethy、Irving W. Wainer

  DOI：10.1021/jm070030d

  日期：2007.6.1

  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.