3-fluoro-5-(2-(trimethylsilyl)ethynyl)benzonitrile | 914948-32-6

• 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-fluoro-5-(2-(trimethylsilyl)ethynyl)benzonitrile
• 英文别名: 3-fluoro-5-[(trimethylsilyl)ethynyl]benzonitrile；ZP-3-53；3-Fluoro-5-((trimethylsilyl)ethynyl)benzonitrile；3-fluoro-5-(2-trimethylsilylethynyl)benzonitrile
• CAS: 914948-32-6
• 化学式: C₁₂H₁₂FNSi
• 分子量: 217.318
• InChiKey: DNCPRRALJDKXID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-fluoro-5-(2-(trimethylsilyl)ethynyl)benzonitrile 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 3-乙炔-5-氟苯甲腈
  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
• 作为产物：
  描述：

  3-溴-5-氟苯腈 以94的产率得到3-fluoro-5-(2-(trimethylsilyl)ethynyl)benzonitrile
  参考文献：
  名称：

  J. Med. Chem. 2007, 50, 3256-3266

  摘要：

  DOI：

文献信息

• 1,6-Dihydro-1,3,5,6-Tetraaza-as-indacene based tricyclic compounds and pharmaceutical compositions comprising same
  申请人：Pitts J. William

  公开号：US20060270654A1

  公开（公告）日：2006-11-30

  The present invention provides for tricyclic compounds having the formula (I), wherein R 1 , R 2 , R 5 , R 6 , R 7 , and R 8 are as described herein. The present invention further provides pharmaceutical compositions comprising such compounds, as well as the use of such compounds for treating inflammatory and immune diseases.

  本发明提供了具有式(I)的三环化合物，其中R1，R2，R5，R6，R7和R8如本文所述。本发明还提供了包含这种化合物的药物组合物，以及使用这种化合物治疗炎症和免疫性疾病的方法。
• 1,6-dihydro-1,3,5,6-tetraaza-as-indacene based tricyclic compounds and pharmaceutical compositions comprising same
  申请人：Bristol-Myers Squibb Company

  公开号：US07737279B2

  公开（公告）日：2010-06-15

  The present invention provides for tricyclic compounds having the formula (I), wherein R1, R2, R5, R6, R7, and R8 are as described herein. The present invention further provides pharmaceutical compositions comprising such compounds, as well as the use of such compounds for treating inflammatory and immune diseases.

  本发明提供了具有以下公式（I）的三环化合物，其中R1、R2、R5、R6、R7和R8如本文所述。本发明还提供了包括这种化合物的制药组合物，以及使用这种化合物治疗炎症和免疫性疾病的方法。
• 1,6-DIHYDRO-1,3,5,6-TETRAAZA-AS-INDACENE BASED TRICYCLIC COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS COMPRISING SAME
  申请人：Pitts William J.

  公开号：US20100210629A1

  公开（公告）日：2010-08-19

  The present invention provides for tricyclic compounds having the formula (I), wherein R 1 , R 2 , R 5 , R 6 , R 7 , and R 8 are as described herein. The present invention further provides pharmaceutical compositions comprising such compounds, as well as the use of such compounds for treating inflammatory and immune diseases.

  本发明提供了具有式（I）的三环化合物，其中R1、R2、R5、R6、R7和R8如本文所述。本发明还提供了包含这些化合物的药物组合物，以及使用这些化合物治疗炎症和免疫性疾病的方法。
• WO2006/122137
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  公开号：——

  公开（公告）日：——
• WO2006/115895
  申请人：——

  公开号：——

  公开（公告）日：——