3-((2-chlorothiazol)-4-ylethynyl)-5-fluorobenzonitrile | 1262778-31-3

• 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-chlorothiazol)-4-ylethynyl)-5-fluorobenzonitrile
• 英文别名: 3-((2-Chlorothiazol)-4-yl)ethynyl)-5-fluorobenzonitrile；3-[2-(2-chloro-1,3-thiazol-4-yl)ethynyl]-5-fluorobenzonitrile
• CAS: 1262778-31-3
• 化学式: C₁₂H₄ClFN₂S
• 分子量: 262.695
• InChiKey: PPAQOEIJUZVTEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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-chlorothiazol)-4-ylethynyl)-5-fluorobenzonitrile 在 potassium fluoride 、 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 二甲基亚砜 为溶剂， 反应 0.17h， 以72%的产率得到3-((2-fluorothiazol-4-yl)ethynyl)-5-fluorobenzonitrile
  参考文献：
  名称：

  Syntheses of 2-Amino and 2-Halothiazole Derivatives as High-Affinity Metabotropic Glutamate Receptor Subtype 5 Ligands and Potential Radioligands for in Vivo Imaging

  摘要：

  The structure of the potent selective mGlu(5) ligand, SP203 (1, 3-fluoro-5-[[2-(fluoromethyl)thiazol-4-yl]ethynyl]benzonitrile), was modified by replacing the 2-fluoromethyl substituent with an amino or halo substituent and by variation of substituents in the distal aromatic ring to provide a series of new high-affinity mGlu(5) ligands. In this series, among the most potent ligands obtained, the 2-chlorothiazoles 7a and 7b and the 2-fluorothiazole 10b showed subnanomolar mGlu(5) affinity. 10b also displayed > 10000-fold selectivity over all other metabotropic receptor subtypes plus a wide range of other receptors and binding sites. The 2-fluorothiazoles 10a and 10b were labeled using [F-18]fluoride ion (t(1/2) = 109.7 min) in moderately high radiochemical yield to provide potential radioligands that may resist troublesome radiodefluorination during the imaging of brain mGlu(5) with position emission tomography. The iodo compound 9b has nanomolar affinity for mGlu(5) and may also serve as a lead to a potential I-123-labeled ligand for imaging brain mGlu(5) with single photon emission computed tomography.

  DOI：

  10.1021/jm101430m
• 作为产物：
  描述：

  5-氨基-3-氟苯腈 在 copper(l) iodide 、 四(三苯基膦)钯 、 亚硝酸丁酯 、 四丁基氟化铵 、 三乙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 2-甲基-1,2-丙二醇 、 乙腈 为溶剂， 反应 0.33h， 生成 3-((2-chlorothiazol)-4-ylethynyl)-5-fluorobenzonitrile
  参考文献：
  名称：

  Syntheses of 2-Amino and 2-Halothiazole Derivatives as High-Affinity Metabotropic Glutamate Receptor Subtype 5 Ligands and Potential Radioligands for in Vivo Imaging

  摘要：

  The structure of the potent selective mGlu(5) ligand, SP203 (1, 3-fluoro-5-[[2-(fluoromethyl)thiazol-4-yl]ethynyl]benzonitrile), was modified by replacing the 2-fluoromethyl substituent with an amino or halo substituent and by variation of substituents in the distal aromatic ring to provide a series of new high-affinity mGlu(5) ligands. In this series, among the most potent ligands obtained, the 2-chlorothiazoles 7a and 7b and the 2-fluorothiazole 10b showed subnanomolar mGlu(5) affinity. 10b also displayed > 10000-fold selectivity over all other metabotropic receptor subtypes plus a wide range of other receptors and binding sites. The 2-fluorothiazoles 10a and 10b were labeled using [F-18]fluoride ion (t(1/2) = 109.7 min) in moderately high radiochemical yield to provide potential radioligands that may resist troublesome radiodefluorination during the imaging of brain mGlu(5) with position emission tomography. The iodo compound 9b has nanomolar affinity for mGlu(5) and may also serve as a lead to a potential I-123-labeled ligand for imaging brain mGlu(5) with single photon emission computed tomography.

  DOI：

  10.1021/jm101430m