(6-bromonaphthalen-2-yloxy)triisopropylsilane | 1186217-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (6-bromonaphthalen-2-yloxy)triisopropylsilane
• 英文别名: (6-bromonaphthalen-2-yl)oxy-tri(propan-2-yl)silane
• CAS: 1186217-25-3
• 化学式: C₁₉H₂₇BrOSi
• 分子量: 379.412
• InChiKey: CPXOWHXUNOFRFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.16
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (6-bromonaphthalen-2-yloxy)triisopropylsilane 在 正丁基锂 、 盐酸羟胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 9.75h， 生成 6-(triisopropylsilyloxy)-2-naphthaldehydeoxime
  参考文献：
  名称：

  Glucose-derived spiro-isoxazolines are anti-hyperglycemic agents against type 2 diabetes through glycogen phosphorylase inhibition

  摘要：

  Glycogen phosphorylase (GP) is a target for the treatment of hyperglycaemia in the context of type 2 diabetes. This enzyme is responsible for the depolymerization of glycogen into glucose thereby affecting the levels of glucose in the blood stream. Twelve new D-glucopyranosylidene-spiro-isoxazolines have been prepared from O-peracylated exo-D-glucals by regio- and stereoselective 1,3-dipolar cycloaddition of nitrile oxides generated in situ by treatment of the corresponding oximes with bleach. This mild and direct procedure appeared to be applicable to a broad range of substrates. The corresponding 0-unprotected spiro-isoxazolines were evaluated as glycogen phosphorylase (GP) inhibitors and exhibited IC50 values ranging from 1 to 800 mu M. Selected inhibitors were further evaluated in vitro using rat and human hepatocytes and exhibited significant inhibitory properties in the primary cell culture. Interestingly, when tested with human hepatocytes, the tetra-O-acetylated spiro-isoxazoline bearing a 2-naphthyl residue showed a much lower IC50 value (2.5 mu M), compared to that of the 0-unprotected analog (19.95 mu M). The most promising compounds were investigated in Zucker fa/fa rat model in acute and sub-chronic assays and decreased hepatic glucose production, which is known to be elevated in type 2 diabetes. This indicates that glucose-based spiro-isoxazolines can be considered as anti-hyperglycemic agents in the context of type 2 diabetes. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.004
• 作为产物：
  描述：

  6-溴-2-萘酚 、 三异丙基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以98%的产率得到(6-bromonaphthalen-2-yloxy)triisopropylsilane
  参考文献：
  名称：

  Glucose-derived spiro-isoxazolines are anti-hyperglycemic agents against type 2 diabetes through glycogen phosphorylase inhibition

  摘要：

  Glycogen phosphorylase (GP) is a target for the treatment of hyperglycaemia in the context of type 2 diabetes. This enzyme is responsible for the depolymerization of glycogen into glucose thereby affecting the levels of glucose in the blood stream. Twelve new D-glucopyranosylidene-spiro-isoxazolines have been prepared from O-peracylated exo-D-glucals by regio- and stereoselective 1,3-dipolar cycloaddition of nitrile oxides generated in situ by treatment of the corresponding oximes with bleach. This mild and direct procedure appeared to be applicable to a broad range of substrates. The corresponding 0-unprotected spiro-isoxazolines were evaluated as glycogen phosphorylase (GP) inhibitors and exhibited IC50 values ranging from 1 to 800 mu M. Selected inhibitors were further evaluated in vitro using rat and human hepatocytes and exhibited significant inhibitory properties in the primary cell culture. Interestingly, when tested with human hepatocytes, the tetra-O-acetylated spiro-isoxazoline bearing a 2-naphthyl residue showed a much lower IC50 value (2.5 mu M), compared to that of the 0-unprotected analog (19.95 mu M). The most promising compounds were investigated in Zucker fa/fa rat model in acute and sub-chronic assays and decreased hepatic glucose production, which is known to be elevated in type 2 diabetes. This indicates that glucose-based spiro-isoxazolines can be considered as anti-hyperglycemic agents in the context of type 2 diabetes. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.004

文献信息

• POLYMERIZABLE COMPOUNDS AND USE THEREOF IN LIQUID CRYSTAL DISPLAYS
  申请人：Taugerbeck Andreas

  公开号：US20130093975A1

  公开（公告）日：2013-04-18

  The present invention relates to polymerisable compounds, to processes and intermediates for the preparation thereof, and to the use thereof for optical, electro-optical and electronic purposes, in particular in liquid-crystal (LC) media and LC displays, especially in LC displays of the PS (“polymer sustained”) or PSA (“polymer sustained alignment”) type.

  本发明涉及可聚合化合物，以及用于其制备的工艺和中间体，以及其在光学、电光和电子方面的用途，特别是在液晶（LC）介质和LC显示器中的应用，特别是在PS（“聚合物持续”）或PSA（“聚合物持续取向”）类型的LC显示器中的应用。
• Polymerizable compounds and use thereof in liquid crystal displays
  申请人：Taugerbeck Andreas

  公开号：US09045683B2

  公开（公告）日：2015-06-02

  The present invention relates to polymerizable compounds, to processes and intermediates for the preparation thereof, and to the use thereof for optical, electro-optical and electronic purposes, in particular in liquid-crystal (LC) media and LC displays, especially in LC displays of the PS (“polymer sustained”) or PSA (“polymer sustained alignment”) type.

  本发明涉及可聚合化合物、其制备过程和中间体，以及其在光学、电光和电子方面的用途，特别是在液晶（LC）介质和LC显示器中，尤其是在PS（“聚合物维持”）或PSA（“聚合物维持对准”）类型的LC显示器中的用途。
• Glucose-derived spiro-isoxazolines are anti-hyperglycemic agents against type 2 diabetes through glycogen phosphorylase inhibition
  作者：David Goyard、Bálint Kónya、Aikaterini S. Chajistamatiou、Evangelia D. Chrysina、Jérémy Leroy、Sophie Balzarin、Michel Tournier、Didier Tousch、Pierre Petit、Cédric Duret、Patrick Maurel、László Somsák、Tibor Docsa、Pál Gergely、Jean-Pierre Praly、Jacqueline Azay-Milhau、Sébastien Vidal

  DOI：10.1016/j.ejmech.2015.12.004

  日期：2016.1

  Glycogen phosphorylase (GP) is a target for the treatment of hyperglycaemia in the context of type 2 diabetes. This enzyme is responsible for the depolymerization of glycogen into glucose thereby affecting the levels of glucose in the blood stream. Twelve new D-glucopyranosylidene-spiro-isoxazolines have been prepared from O-peracylated exo-D-glucals by regio- and stereoselective 1,3-dipolar cycloaddition of nitrile oxides generated in situ by treatment of the corresponding oximes with bleach. This mild and direct procedure appeared to be applicable to a broad range of substrates. The corresponding 0-unprotected spiro-isoxazolines were evaluated as glycogen phosphorylase (GP) inhibitors and exhibited IC50 values ranging from 1 to 800 mu M. Selected inhibitors were further evaluated in vitro using rat and human hepatocytes and exhibited significant inhibitory properties in the primary cell culture. Interestingly, when tested with human hepatocytes, the tetra-O-acetylated spiro-isoxazoline bearing a 2-naphthyl residue showed a much lower IC50 value (2.5 mu M), compared to that of the 0-unprotected analog (19.95 mu M). The most promising compounds were investigated in Zucker fa/fa rat model in acute and sub-chronic assays and decreased hepatic glucose production, which is known to be elevated in type 2 diabetes. This indicates that glucose-based spiro-isoxazolines can be considered as anti-hyperglycemic agents in the context of type 2 diabetes. (C) 2015 Elsevier Masson SAS. All rights reserved.