3-(2-(2-methylthiazol-4-yl)ethynyl)-5-iodobenzonitrile | 1312923-88-8

• 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-iodobenzonitrile
• 英文别名: 3-iodo-5-((2-methylthiazol-4-yl)ethynyl)benzonitrile；3-iodo-5-[2-(2-methyl-1,3-thiazol-4-yl)ethynyl]benzonitrile
• CAS: 1312923-88-8
• 化学式: C₁₃H₇IN₂S
• 分子量: 350.182
• InChiKey: GEBAHYAEJWVOES-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：
  0.08
• 拓扑面积：
  64.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-(2-methylthiazol-4-yl)ethynyl)-5-iodobenzonitrile 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-iodobenzonitrile 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：

  3,5-diiodobenzoyl chloride 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 21.0h， 生成 3-(2-(2-methylthiazol-4-yl)ethynyl)-5-iodobenzonitrile
  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

• PROCESSES AND REAGENTS FOR MAKING DIARYLIODONIUM SALTS
  申请人：Ground Fluor Pharmaceuticals, Inc.

  公开号：US20140121371A1

  公开（公告）日：2014-05-01

  This disclosure relates to processes and reagents for making diaryliodonium salts, which are useful for the preparation of fluorinated, iodinated, astatinated and radiofluorinated aromatic compounds.

  这项披露涉及用于制备二芳基碘盐的工艺和试剂，该类试剂可用于制备氟化、碘化、砹化和放射性氟化芳香化合物。
• Syntheses of mGluR5 PET radioligands through the radiofluorination of diaryliodonium tosylates
  作者：Sanjay Telu、Joong-Hyun Chun、Fabrice G. Siméon、Shuiyu Lu、Victor W. Pike

  DOI：10.1039/c1ob05555k

  日期：——

  3-Fluoro-1-((thiazol-4-yl)ethynyl)benzenes constitute an important class of high-affinity metabotropic glutamate subtype 5 receptor (mGluR5) ligands, some of which have been labeled with fluorine-18 (t1/2 = 109.7 min), to provide radioligands for molecular imaging of brain mGluR5 in living animal and human subjects with positron emission tomography (PET). Labeling in the 3-fluoro position of such ligands can be achieved through aromatic nucleophilic substitution of a halide leaving group with [18F]fluoride ion when a weakly activating m-nitrile group is present, but is generally very low yielding (<8%). Here we used a microfluidic reaction platform to show that greatly enhanced (up to 6-fold) radiochemical yields can be achieved from suitably synthesized diaryliodonium tosylate precursors. The presence of a m-nitrile or other activating group is not required. Similar conditions were adopted in a more conventional automated radiochemistry platform having a single-pot reactor, to produce mGluR5 radioligands with useful radioactivities for PET imaging.

  3-氟-1-((噻唑-4-基)乙炔基)苯系物是一类重要的高亲和性代谢谷氨酸亚型 5 受体（mGluR5）配体，其中一些已用氟-18（t1/2 = 109.7 分钟）标记，为正电子发射断层扫描（PET）对活体动物和人体脑部 mGluR5 进行分子成像提供了放射性配体。当存在弱活化间腈基团时，可通过芳香族亲核取代卤化物离去基团与[18F]氟离子来实现此类配体 3-氟位置的标记，但通常产率很低（<8%）。在这里，我们利用微流体反应平台证明，通过适当合成二芳碘对甲苯磺酸盐前体，可大大提高放射化学产率（高达 6 倍）。无需存在间腈或其他活化基团。在具有单锅反应器的更传统的自动化放射化学平台中也采用了类似的条件，以生产具有 PET 成像有用放射性活性的 mGluR5 放射性配体。
• US9278959B2
  申请人：——

  公开号：US9278959B2

  公开（公告）日：2016-03-08
• [EN] PROCESSES AND REAGENTS FOR MAKING DIARYLIODONIUM SALTS<br/>[FR] PROCÉDÉS ET RÉACTIFS POUR FABRIQUER DES SELS DE DIARYLIODONIUM
  申请人：GROUND FLUOR PHARMACEUTICALS INC

  公开号：WO2014066772A1

  公开（公告）日：2014-05-01

  This disclosure relates to processes and reagents for making diaryliodonium salts, which are useful for the preparation of fluorinated, iodinated, astatinated and radiofluorinated aromatic compounds.
• Potent mGluR5 antagonists: Pyridyl and thiazolyl-ethynyl-3,5-disubstituted-phenyl series
  作者：David Alagille、Herve DaCosta、Yelin Chen、Kamondanai Hemstapat、Alice Rodriguez、Ronald M. Baldwin、Jeffrey P. Conn、Gilles D. Tamagnan

  DOI：10.1016/j.bmcl.2011.04.047

  日期：2011.6

  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.