3-(2-(2-methylthiazol-4-yl)ethynyl)-5-fluorobenzonitrile | 864063-09-2

• 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-methylthiazol-4-yl)ethynyl)-5-fluorobenzonitrile
• 英文别名: 3-fluoro-5-cyano-1-(2-methylthiazol-4-ylethynyl)benzene；3-fluoro-5-((2-methylthiazol-4-yl)ethynyl)benzonitrile；3-fluoro-5-[2-(2-methyl-1,3-thiazol-4-yl)ethynyl]benzonitrile
• CAS: 864063-09-2
• 化学式: C₁₃H₇FN₂S
• 分子量: 242.276
• InChiKey: YPCGRVYMABSMOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  396.2±37.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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-methylthiazol-4-yl)ethynyl)-5-fluorobenzonitrile 在 盐酸 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 0.25h， 生成 3-(2-(2-methylthiazol-4-yl)ethynyl)-5-fluorobenzonitrile hydrochloride
  参考文献：
  名称：

  Potent mGluR5 antagonists: Pyridyl and thiazolyl-ethynyl-3,5-disubstituted-phenyl series

  摘要：

  We report the synthesis of four series of 3,5-disubstituted-phenyl ligands targeting the metabotropic glutamate receptor subtype 5: (2-methylthiazol-4-yl)ethynyl (1a-j,), (6-methylpyridin-2-yl)ethynyl (2a-j), (5-methylpyridin-2-yl)ethynyl (3a-j,), and (pyridin-2-yl)ethynyl (4a-j,). The compounds were evaluated for antagonism of glutamate-mediated mobilization of internal calcium in an mGluR5 in vitro assay. All compounds were found to be full antagonists and exhibited low nanomolar to subnanomolar activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.047
• 作为产物：
  描述：

  3-溴-5-氟苯甲酰氯 在 bis-triphenylphosphine-palladium(II) chloride 、 ammonium hydroxide 、 copper(l) iodide 、 氯化亚砜 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 3-(2-(2-methylthiazol-4-yl)ethynyl)-5-fluorobenzonitrile
  参考文献：
  名称：

  Potent mGluR5 antagonists: Pyridyl and thiazolyl-ethynyl-3,5-disubstituted-phenyl series

  摘要：

  We report the synthesis of four series of 3,5-disubstituted-phenyl ligands targeting the metabotropic glutamate receptor subtype 5: (2-methylthiazol-4-yl)ethynyl (1a-j,), (6-methylpyridin-2-yl)ethynyl (2a-j), (5-methylpyridin-2-yl)ethynyl (3a-j,), and (pyridin-2-yl)ethynyl (4a-j,). The compounds were evaluated for antagonism of glutamate-mediated mobilization of internal calcium in an mGluR5 in vitro assay. All compounds were found to be full antagonists and exhibited low nanomolar to subnanomolar activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.047

文献信息

• Alkyne derivatives as tracers for metabotropic glutamate receptor binding
  申请人：Cosford Peter Nicholas David

  公开号：US20070060618A1

  公开（公告）日：2007-03-15

  The present invention is directed to isotopically labeled alkyne derivative compounds, particularly 11 C, 13 C, 14 C, 18 F, 15 O, 13 N, 35 S, 2 H, and 3 H labeled compounds. In particular, the present invention is directed to 11 C, 13 C, 14 C, 18 F, 15 O, 13 N, 35 S, 2 H, and 3 H labeled heterocyclic alkynes and methods of their preparation. The present invention further includes a method of use of the 11 C, 18 F, 15 O, or 13 N labeled heterocyclic alkyne compounds as tracers in positron emission tomography (PET) imaging, particularly in the study of metabolic conditions in mammals, specifically conditions modulated by metabotropic glutamate receptors subtype 5 (mGluR5).

  本发明涉及同位素标记的炔基衍生物化合物，特别是11C、13C、14C、18F、15O、13N、35S、2H和3H标记的化合物。具体而言，本发明涉及11C、13C、14C、18F、15O、13N、35S、2H和3H标记的杂环炔烃及其制备方法。本发明还包括将11C、18F、15O或13N标记的杂环炔烃化合物用作正电子发射断层扫描（PET）成像中的示踪剂的使用方法，特别是在哺乳动物代谢状况的研究中，特别是通过代谢型谷氨酸受体亚型5（mGluR5）调节的状况。
• Enhanced copper-mediated ¹⁸F-fluorination of aryl boronic esters provides eight radiotracers for PET applications
  作者：Sean Preshlock、Samuel Calderwood、Stefan Verhoog、Matthew Tredwell、Mickael Huiban、Antje Hienzsch、Stefan Gruber、Thomas C. Wilson、Nicholas J. Taylor、Thomas Cailly、Michael Schedler、Thomas Lee Collier、Jan Passchier、René Smits、Jan Mollitor、Alexander Hoepping、Marco Mueller、Christophe Genicot、Joël Mercier、Véronique Gouverneur

  DOI：10.1039/c6cc03295h

  日期：——

  Eight clinically relevant radiotracers were isolated applying a Cu-mediated non-carrier added nucleophilic ¹⁸F-fluorination of arylboronic ester precursors.

  使用铜介导的非载体添加亲核性¹⁸F-氟化技术，从芳基硼酸酯前体中分离出了八种临床相关的放射性示踪剂。
• Iodonium Cyclophanes for SECURE Arene Functionalization
  申请人：DiMagno Stephen

  公开号：US20110190505A1

  公开（公告）日：2011-08-04

  This disclosure relates to compounds, reagents, and methods useful in the synthesis of aryl fluorides, for example, in the preparation of 18 F labeled radiotracers. For example, this disclosure provides universal “locked” aryl substituents that result in StereoElectronic Control of Unidirectional Reductive Elimination (SECURE) from diaryliodonium salts. The reagents and methods provided herein may be used to access a broad range of compounds, including aromatic compounds, heteroaromatic compounds, amino acids, nucleotides, and synthetic compounds.

  本公开涉及化合物、试剂和合成芳基氟化物的方法，例如在制备18F标记的放射追踪剂中。例如，本公开提供了通用的“锁定”芳基取代基，从二芳基碘盐中结果的立体电子控制单向还原消除（SECURE）。本文所提供的试剂和方法可用于访问广泛的化合物，包括芳香族化合物、杂环芳香族化合物、氨基酸、核苷酸和合成化合物。
• Fluorination of Aromatic Ring Systems
  申请人：DiMagno Stephen Gregory

  公开号：US20110313170A1

  公开（公告）日：2011-12-22

  This disclosure relates to reagents and methods useful in the synthesis of aryl fluorides, for example, in the preparation of 18 F labeled radiotracers. The reagents and methods provided herein may be used to access a broad range of compounds, including aromatic compounds, heteroaromatic compounds, amino acids, nucleotides, and synthetic compounds.

  本公开涉及到试剂和方法，可用于合成芳基氟化物，例如制备18F标记的放射性示踪剂。本文提供的试剂和方法可用于获得广泛的化合物，包括芳香族化合物、杂环芳香族化合物、氨基酸、核苷酸和合成化合物。
• FLUORINATION OF AROMATIC RING SYSTEMS
  申请人：Dimagno Stephen

  公开号：US20120004417A1

  公开（公告）日：2012-01-05

  This disclosure relates to reagents and methods useful in the synthesis of aryl fluorides, for example, in the preparation of 18 F labeled radiotracers. The reagents and methods provided herein may be used to access a broad range of compounds, including aromatic compounds, heteroaromatic compounds, amino acids, nucleotides, and synthetic compounds.

  本公开涉及与合成芳基氟化物有关的试剂和方法，例如，在制备18F标记的放射性示踪剂时。本文提供的试剂和方法可用于访问广泛的化合物，包括芳香族化合物，杂环芳香族化合物，氨基酸，核苷酸和合成化合物。