tetraethyl ((2-methoxy-1,4-phenylene)bis(methylene))bis(phosphonate) | 906533-44-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tetraethyl ((2-methoxy-1,4-phenylene)bis(methylene))bis(phosphonate)
• 英文别名: 1,4-Bis(diethoxyphosphorylmethyl)-2-methoxybenzene
• CAS: 906533-44-6
• 化学式: C₁₇H₃₀O₇P₂
• 分子量: 408.369
• InChiKey: MBDSIIAAUXKJHT-UHFFFAOYSA-N

物化性质

• 沸点：
  514.7±50.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tetraethyl ((2-methoxy-1,4-phenylene)bis(methylene))bis(phosphonate) 在 potassium tert-butylate 、 氯化铵 、 锌 作用下， 以 二乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  神经标记的苯乙烯基型染料的荧光现象

  摘要：

  合成了几类不同取代的苯乙烯基型染料，其目标是将它们的预期荧光特性尽可能地扩展为红色，这是因为它们必须保持类似药物的特性并保持与其生物学靶标的高亲和力结合。我们报告了一系列苯乙烯基染料（d1 - d14）的合成，光学性质，以及这些被长共轭π系统（d7 - d10）分隔的供体-受体对中某些对的异常光物理行为）。我们进一步描述了具有两个不同基态构象异构体的不寻常的双重发射行为，它们在推挽式染料体系（d7，d9和d10）中可以分别被激发到局部激发（LE）和扭曲的分子内电荷转移（TICT）激发态。此外，在染料系统d7和d8中，其中氨基衍生物d7在极性介质中显示双重发射，而N，N-二甲基衍生物d8和其他甲基化衍生物d12 - d14出现了意外的发射行为仅显示LE排放，但不显示任何TICT排放。基于光物理和神经结合研究，我们选择了表现出神经组织切片最强荧光染色的化合物。随后使用内部开发的小动物多光谱成像

  DOI：

  10.1016/j.jphotochem.2015.05.033
• 作为产物：
  描述：

  2,5-二甲基苯甲醚 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 18.0h， 生成 tetraethyl ((2-methoxy-1,4-phenylene)bis(methylene))bis(phosphonate)
  参考文献：
  名称：

  Bis-pyridylethenyl benzene as novel backbone for amyloid-β binding compounds

  摘要：

  Detection of cerebral beta-amyloid (A beta) by targeted contrast agents is of great interest for in vivo diagnosis of Alzheimer's disease (AD). Partly because of their planar structure several bis-styrylbenzenes have been previously reported as potential A beta imaging agents. However, these compounds are relatively hydrophobic, which likely limits their in vivo potential. Based on their structures, we hypothesized that less hydrophobic bis-pyridylethenylbenzenes may also label amyloid. We synthesized several bis-pyridylethenylbenzenes and tested whether these compounds indeed display improved solubility and lower LogP values, and studied their fluorescent properties and A beta binding characteristics. Bis-pyridylethenylbenzenes showed a clear affinity for A beta plaques on both human and murine AD brain sections. Competitive binding experiments suggested a different binding site than Chrysamine G, a well-known stain for amyloid. With a LogP value between 3 and 5, most bis-pyridylethenylbenzenes were able to enter the brain and label murine amyloid in vivo with the bis(4-pyridylethenyl) benzenes showing the most favorable characteristics. In conclusion, the presented results suggest that bis-pyridylethenylbenzene may serve as a novel backbone for amyloid imaging agents. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2016.05.022

文献信息

• IMAGING OF MYELIN BASIC PROTEIN
  申请人：Tan Hehir Cristina Abucay

  公开号：US20100310457A1

  公开（公告）日：2010-12-09

  The present invention relates to methods for myelin basic protein detection comprises identifying a subject at risk of or diagnosed with a myelin-associated neuropathy, parenterally administering to the subject the agent, and determining myelination in the subject by detecting binding to myelin basic protein. Methods for the detection of myelin and a quantitative measurement of its local concentration in a sample using an agent with specific binding to myelin basic protein are also provided as is a kit containing the agent or its derivatives for use in detecting myelin basic protein

  本发明涉及用于髓鞘碱性蛋白检测的方法，包括识别患有或有患髓鞘相关神经病变风险的受试者，向受试者经肠外途径给予药物，并通过检测与髓鞘碱性蛋白结合来确定受试者的髓鞘生成情况。本发明还提供了用具有特异性结合髓鞘碱性蛋白的药物在样品中检测髓鞘及其局部浓度的定量测量方法，以及包含该药物或其衍生物的试剂盒，用于检测髓鞘碱性蛋白。
• Polyfluorinated bis-styrylbenzenes as amyloid-β plaque binding ligands
  作者：Rob J.A. Nabuurs、Varsha V. Kapoerchan、Athanasios Metaxas、Sanne de Jongh、Maaike de Backer、Mick M. Welling、Wim Jiskoot、Albert D. Windhorst、Hermen S. Overkleeft、Mark A. van Buchem、Mark Overhand、Louise van der Weerd

  DOI：10.1016/j.bmc.2014.02.054

  日期：2014.4

  Detection of cerebral beta-amyloid (A beta) by targeted contrast agents remains of great interest to aid the in vivo diagnosis of Alzheimer's disease (AD). Bis-styrylbenzenes have been previously reported as potential A beta imaging agents. To further explore their potency as F-19 MRI contrast agents we synthetized several novel fluorinated bis-styrylbenzenes and studied their fluorescent properties and amyloid-beta binding characteristics. The compounds showed a high affinity for Ab plaques on murine and human brain sections. Interestingly, competitive binding experiments demonstrated that they bound to a different binding site than chrysamine G. Despite their high logP values, many bis-styrylbenzenes were able to enter the brain and label murine amyloid in vivo. Unfortunately initial post-mortem F-19 NMR studies showed that these compounds as yet do not warrant further MRI studies due to the reduction of the 19F signal in the environment of the brain. (C) 2014 Published by Elsevier Ltd.
• Fluorescence phenomena in nerve-labeling styryl-type dyes
  作者：Tiberiu M. Siclovan、Rong Zhang、Victoria Cotero、Anshika Bajaj、Dmitry V. Dylov、Siavash Yazdanfar、Randall L. Carter、Cristina A.Tan Hehir、Arunkumar Natarajan

  DOI：10.1016/j.jphotochem.2015.05.033

  日期：2016.2

  classes of diversely substituted styryl type dyes have been synthesized with the goal of extending their expected fluorescent properties as much toward red as possible given the constraint that they maintain drug-like properties and retain high affinity binding to their biological target. We report on the synthesis, optical properties of a series of styryl dyes (d1–d14), and the anomalous photophysical

  合成了几类不同取代的苯乙烯基型染料，其目标是将它们的预期荧光特性尽可能地扩展为红色，这是因为它们必须保持类似药物的特性并保持与其生物学靶标的高亲和力结合。我们报告了一系列苯乙烯基染料（d1 - d14）的合成，光学性质，以及这些被长共轭π系统（d7 - d10）分隔的供体-受体对中某些对的异常光物理行为）。我们进一步描述了具有两个不同基态构象异构体的不寻常的双重发射行为，它们在推挽式染料体系（d7，d9和d10）中可以分别被激发到局部激发（LE）和扭曲的分子内电荷转移（TICT）激发态。此外，在染料系统d7和d8中，其中氨基衍生物d7在极性介质中显示双重发射，而N，N-二甲基衍生物d8和其他甲基化衍生物d12 - d14出现了意外的发射行为仅显示LE排放，但不显示任何TICT排放。基于光物理和神经结合研究，我们选择了表现出神经组织切片最强荧光染色的化合物。随后使用内部开发的小动物多光谱成像
• Bis-pyridylethenyl benzene as novel backbone for amyloid-β binding compounds
  作者：Rob J.A. Nabuurs、Varsha V. Kapoerchan、Athanasios Metaxas、Sarah Hafith、Maaike de Backer、Mick M. Welling、Wim Jiskoot、Adrianus M.C.H. van den Nieuwendijk、Albert D. Windhorst、Herman S. Overkleeft、Mark A. van Buchem、Mark Overhand、Louise van der Weerd

  DOI：10.1016/j.bmc.2016.05.022

  日期：2016.12

  Detection of cerebral beta-amyloid (A beta) by targeted contrast agents is of great interest for in vivo diagnosis of Alzheimer's disease (AD). Partly because of their planar structure several bis-styrylbenzenes have been previously reported as potential A beta imaging agents. However, these compounds are relatively hydrophobic, which likely limits their in vivo potential. Based on their structures, we hypothesized that less hydrophobic bis-pyridylethenylbenzenes may also label amyloid. We synthesized several bis-pyridylethenylbenzenes and tested whether these compounds indeed display improved solubility and lower LogP values, and studied their fluorescent properties and A beta binding characteristics. Bis-pyridylethenylbenzenes showed a clear affinity for A beta plaques on both human and murine AD brain sections. Competitive binding experiments suggested a different binding site than Chrysamine G, a well-known stain for amyloid. With a LogP value between 3 and 5, most bis-pyridylethenylbenzenes were able to enter the brain and label murine amyloid in vivo with the bis(4-pyridylethenyl) benzenes showing the most favorable characteristics. In conclusion, the presented results suggest that bis-pyridylethenylbenzene may serve as a novel backbone for amyloid imaging agents. (C) 2016 Published by Elsevier Ltd.