3-(2-(2-(bromomethyl)thiazol-4-yl)ethynyl)-5-fluorobenzonitrile | 945933-49-3

• 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: 3-(2-(2-(bromomethyl)thiazol-4-yl)ethynyl)-5-fluorobenzonitrile
• 英文别名: 3-{2-[2-(bromomethyl)thiazol-4-yl]ethynyl}-5-fluorobenzonitrile；3-[2-[2-(Bromomethyl)-1,3-thiazol-4-yl]ethynyl]-5-fluorobenzonitrile
• CAS: 945933-49-3
• 化学式: C₁₃H₆BrFN₂S
• 分子量: 321.172
• InChiKey: UJBSAONODRZBMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  64.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-(2-(bromomethyl)thiazol-4-yl)ethynyl)-5-fluorobenzonitrile 在 potassium carbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 3-fluoro-5-(2-(2-((18F)-fluoromethyl)thiazol-4-yl)ethynyl)benzonitrile
  参考文献：
  名称：

  Integration of a microwave reactor with synthia to provide a fully automated radiofluorination module

  摘要：

  DOI：

  10.1002/jlcr.1196
• 作为产物：
  描述：

  3-fluoro-5-(2-(trimethylsilyl)ethynyl)benzonitrile 在 copper(l) iodide 、 四(三苯基膦)钯 四溴化碳 、 四丁基氟化铵 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 2.17h， 生成 3-(2-(2-(bromomethyl)thiazol-4-yl)ethynyl)-5-fluorobenzonitrile
  参考文献：
  名称：

  Synthesis and Simple ¹⁸F-Labeling of 3-Fluoro-5-(2-(2-(fluoromethyl)thiazol-4-yl)ethynyl)benzonitrile as a High Affinity Radioligand for Imaging Monkey Brain Metabotropic Glutamate Subtype-5 Receptors with Positron Emission Tomography

  摘要：

  2-Fluoromethyl analogs of (3-[(2-methyl-1,3-thiazol-4yl)ethynyl]pyridine) were synthesized as potential ligands for metabotropic glutamate subtype-5 receptors (mGluR5s). One of these, namely, 3-fluoro-5-(2-(2-(fluoromethyl)thiazol-4-yl)ethynyl)benzonitrile (3), was found to have exceptionally high affinity (IC50 = 36 pM) and potency in a phosphoinositol hydrolysis assay (IC50 = 0.714 pM) for mGluR5. Compound 3 was labeled with fluorine-18 (t(1/2) = 109.7 min) in high radiochemical yield (87%) by treatment of its synthesized bromomethyl analog (17) with [F-18]fluoride ion and its radioligand behavior was assessed with positron emission tomography (PET). Following intravenous injection of [F-18]3 into rhesus monkey, radioactivity was avidly taken up into brain with high uptake in mGluR5 receptor-rich regions such as striata. [F-18]3 was stable in monkey plasma and human whole blood in vitro and in monkey and human brain homogenates. In monkey in vivo, a single polar radiometabolite of [F-18]3 appeared rapidly in plasma. [F-18]3 merits further evaluation as a PET radioligand for mGluR5 in human subjects.

  DOI：

  10.1021/jm0701268

文献信息

• A Short and Efficient Synthesis of 3-{2-[2-(Bromomethyl)thiazol-4-yl]-ethynyl}-5-fluorobenzonitrile: A Precursor for PET Radioligand [18F]SP203
  作者：Kenneth Rehder、Madathil Gopinathan、Chunyang Jin

  DOI：10.1055/s-0029-1216787

  日期：2009.6

  An improved synthesis of 3-2-[2-(bromomethyl)thia­zol-4-yl]ethynyl}-5-fluorobenzonitrile, a precursor for PET radioligand [¹8F]SP203, is described, wherein a new synthon was employed for Sonogashira coupling with 3-bromo-5-fluorobenzonitrile. The new five-step synthesis provided the title compound in 56% overall yield starting from 4-bromo-2-formylthiazole. PET ligand - fluorine - Sonogashira coupling

  描述了一种改进的3- 2- [2-（溴甲基）噻唑-4-基]乙炔基} -5-氟苄腈（PET放射性配体[ 18 F] SP203的前体）的合成方法，其中将新的合成子用于Sonogashira与3-溴-5-氟苄腈偶联。新的五步合成法从4-溴-2-甲酰基噻唑开始，提供了总收率56％的标题化合物。 PET配体-氟-Sonogashira偶联-钯-溴化
• J. Med. Chem. 2007, 50, 3256-3266
  作者：

  DOI：——

  日期：——