(2-(3-bromopropoxy)ethoxy)(tert-butyl)dimethylsilane | 1451015-27-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2-(3-bromopropoxy)ethoxy)(tert-butyl)dimethylsilane
• 英文别名: [2-(3-Bromopropoxy)ethoxy](tert-butyl)dimethylsilane；2-(3-bromopropoxy)ethoxy-tert-butyl-dimethylsilane
• CAS: 1451015-27-2
• 化学式: C₁₁H₂₅BrO₂Si
• 分子量: 297.308
• InChiKey: RHZCUJSNCLIKOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-(3-bromopropoxy)ethoxy)(tert-butyl)dimethylsilane 在 四丁基氟化铵 、 caesium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.08h， 生成 2-(3-(3-(((3s,5s,7s)-adamantan-1-yl)carbamoyl)-8-methoxy-4-oxoquinolin-1(4H)-yl)propoxy)ethyl methanesulfonate
  参考文献：
  名称：

  Evaluation of 4-oxo-quinoline-based CB2 PET radioligands in R6/2 chorea huntington mouse model and human ALS spinal cord tissue

  摘要：

  The cannabinoid receptor 2 (CB2) has been implicated in a series of neurodegenerative disorders and has emerged as an interesting biological target for therapeutic as well as diagnostic purposes. In the present work, we describe an improved radiosynthetic approach to obtain the previously reported CB2-specific PET radioligand [F-18]RS-126 in higher radiochemical yields and molar activities. Additionally, the study revealed that prolongation of the [F-18]RS-126 fluoroalkyl side chain ultimately leads to an improved stability towards mouse liver enzymes but is accompanied by a reduction in selectivity over the cannabinoid receptor 1 (CB1). Huntington-related phenotypic changes as well as striatal D2R down regulation were confirmed for the transgenic R6/2 mouse model. CB2 upregulation in R6/2 Chorea Huntington mice was observed in hippocampus, cortex, striatum and cerebellum by qPCR, however, these results could not be confirmed at the protein level by PET imaging. Furthermore, we evaluated the utility of the newly developed [C-11]RS-028, a potent [F-18]RS-126 derivative with increased polarity and high selectivity over CB1 in post-mortem human ALS spinal cord and control tissue. Applying in vitro autoradiography, the translational relevance of CB2 imaging was demonstrated by the specific binding of [C-11]RS-028 to post-mortem human ALS spinal cord tissue. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.12.097
• 作为产物：
  描述：

  叔丁基二甲基羟乙氧基硅烷 在 indium(III) bromide 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 23.5h， 生成 (2-(3-bromopropoxy)ethoxy)(tert-butyl)dimethylsilane
  参考文献：
  名称：

  Fluorinated pyridylacetylene derivatives as tracers

  摘要：

  这项发明涉及一种化合物，其化学式为（I） 其中F为19F或18F，以自由碱基或酸盐形式存在。在其放射性形式中，使用含有18F的化合物作为大脑和外周神经系统组织或其他体内或体外含有mGlu5受体的组织的放射成像标记物。

  公开号：

  EP2671872A1

文献信息

• [EN] FLUORINATED PYRIDYLACETYLENE DERIVATIVES AS TRACERS<br/>[FR] DÉRIVÉS FLUORÉS DE PYRIDYLACÉTYLÈNE EN TANT QUE TRACEURS
  申请人：EIDGENOESS TECH HOCHSCHULE

  公开号：WO2013182411A1

  公开（公告）日：2013-12-12

  The invention relates to a novel compound of formula (I) wherein F is 19F or 18F, in free base or acid addition salt form. In its radioactive form with 18F, the compound is useuful as a marker for radioimaging of brain and peripheral nervous system tissues or other tissues containing mGlu5 receptors in vitro or in vivo.

  这项发明涉及一种新的化合物，其化学式为（I），其中F为19F或18F，以自由碱或酸盐形式存在。在其放射性形式中，使用含有18F的该化合物作为大脑和外周神经系统组织或其他体内或体外含有mGlu5受体的组织的放射成像标记物。
• Synthesis and In Vitro Evaluation of E- and Z-Geometrical Isomers of PSS232 as Potential Metabotropic Glutamate Receptors Subtype 5 (mGlu5) Binders
  作者：Selena Milicevic Sephton、Simon Ametamey、Linjing Mu、Martina Dragic、Stefanie Krämer、Roger Schibli

  DOI：10.1055/s-0033-1338843

  日期：——

  Based on the core structure of [C-11]-ABP688, our group developed a novel fluorine-18 labeled PET radiotracer, (E)-[F-18]-PSS232, with significantly improved in vivo properties compared to the earlier fluorine-18 derivative [F-18]-FDEGPECO. The synthetic approach used to obtain PSS232 and the radiolabeling precursor mesylate is disclosed as well as the evaluation of the two geometrical isomers of PSS232. In vitro displacement assays showed higher binding affinity of the E-geometrical isomer (1 nM vs 15 nM, for Z-isomer), which was, for this reason, selected for radiolabeling. One-step radiolabeling conditions (K-222/F-18(-), DMSO, 95 degrees C, 10 min) to synthesize (E)-[F-18]- PSS232 from the mesylate via nucleophilic substitution are described. At ambient temperature, (E)-[F-18]-PSS232, with log D-7.4 value of 2.0, was chemically stable over six hours in the presence of sodium ascorbate as a radical scavenger.