2-bromo-4-(phenylethynyl)thiazole | 1130298-11-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-bromo-4-(phenylethynyl)thiazole
• 英文别名: 2-bromo-(4-phenylacetylene)thiazole；2-Bromo-4-(2-phenylethynyl)-1,3-thiazole
• CAS: 1130298-11-1
• 化学式: C₁₁H₆BrNS
• 分子量: 264.145
• InChiKey: BPRBJZXZXYLIRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 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：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-4-(phenylethynyl)thiazole 在 potassium fluoride 作用下， 以 二甲基亚砜 为溶剂， 以46%的产率得到2-fluoro-4-(phenylethynyl)thiazole
  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：

  4-(phenylethynyl)thiazol-2-amine 在 亚硝酸丁酯 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以83%的产率得到2-bromo-4-(phenylethynyl)thiazole
  参考文献：
  名称：

  2-氨基-1,3-噻唑与铜盐的高效和区域选择性卤化

  摘要：

  单卤和二卤 1,3-噻唑衍生物可以在温和条件下由 2-氨基-1,3-噻唑高效且选择性地制备。在铜 (I) 或铜 (II) 氯化物、溴化物或碘化物直接存在于溶液中或与负载的卤化铜一起存在时，卤化很容易进行。

  DOI：

  10.1021/jo802799c

文献信息

• 2-FLUOROTHIAZOLE DERIVATIVES USEFUL AS IMAGING AGENTS; METHODS OF SYNTHESIS, AND METHODS OF USE
  申请人：Pike Victor W.

  公开号：US20110098326A1

  公开（公告）日：2011-04-28

  Novel 18 F-labeled thiazole derivatives useful for imaging of metabotropic glutamate subtype 5 receptors (mGluR5) in living mammalian brain are disclosed herein. Also disclosed herein is a synthetic method for making the claimed thiazole derivatives under thermal heating or microwave conditions for aryl thioethers that provides the compounds in high yield. Imaging methods in which the claimed 18 F-labeled thiazole derivatives are used as imaging agents are also disclosed. Halogen substituted thiazole derivative disclosed herein are also useful as therapeutic agents. Methods of treating mGluR5 mediated disorders with certain halogen substituted thiazole derivatives are disclosed.

  本文披露了一种用于成像哺乳动物大脑中代谢型谷氨酸亚型5受体（mGluR5）的Novel18F标记噻唑衍生物。本文还披露了一种合成所声称的噻唑衍生物的方法，该方法在热加热或微波条件下用于芳基硫醚，可高产得到化合物。本文还披露了使用所声称的18F标记噻唑衍生物作为成像剂的成像方法。本文还披露了卤代噻唑衍生物也可用作治疗剂。本文还披露了使用某些卤代噻唑衍生物治疗mGluR5介导的疾病的方法。
• The [18F]2-fluoro-1,3-thiazolyl moiety—an easily-accessible structural motif for prospective molecular imaging radiotracers
  作者：Fabrice G. Siméon、Matthew T. Wendahl、Victor W. Pike

  DOI：10.1016/j.tetlet.2010.09.037

  日期：2010.11

  2-Fluoro-1,3-thiazoles were rapidly and efficiently labeled with no-carrier-added fluorine-18 (t(1/2) = 109.7 min) by treatment of readily prepared 2-halo precursors with cyclotron-produced [F-18]fluoride ion. The [F-18]2-fluoro-1,3-thiazolyl moiety constitutes a new and easily-labeled structural motif for prospective molecular imaging radiotracers. Published by Elsevier Ltd.
• Syntheses of 2-Amino and 2-Halothiazole Derivatives as High-Affinity Metabotropic Glutamate Receptor Subtype 5 Ligands and Potential Radioligands for in Vivo Imaging
  作者：Fabrice G. Siméon、Matthew T. Wendahl、Victor W. Pike

  DOI：10.1021/jm101430m

  日期：2011.2.10

  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.
• Efficient and Regioselective Halogenations of 2-Amino-1,3-thiazoles with Copper Salts
  作者：Fabrice G. Siméon、Matthew T. Wendahl、Victor W. Pike

  DOI：10.1021/jo802799c

  日期：2009.3.20

  dihalo 1,3-thiazole derivatives can be efficiently and selectively prepared under mild conditions from 2-amino-1,3-thiazoles. Halogenations proceed easily in the presence of copper(I) or copper(II) chlorides, bromides, or iodides directly in solution or with supported copper halides.

  单卤和二卤 1,3-噻唑衍生物可以在温和条件下由 2-氨基-1,3-噻唑高效且选择性地制备。在铜 (I) 或铜 (II) 氯化物、溴化物或碘化物直接存在于溶液中或与负载的卤化铜一起存在时，卤化很容易进行。