2-(2-chlorothiazol-4-yl)ethynyltrimethylsilane | 1262778-26-6

• 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-(2-chlorothiazol-4-yl)ethynyltrimethylsilane
• 英文别名: 2-chloro-4-((trimethylsilyl)ethynyl)thiazole；2-(2-chloro-1,3-thiazol-4-yl)ethynyl-trimethylsilane
• CAS: 1262778-26-6
• 化学式: C₈H₁₀ClNSSi
• 分子量: 215.779
• InChiKey: ZLAJSOMTTXQPPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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-(2-chlorothiazol-4-yl)ethynyltrimethylsilane 在 potassium fluoride 、 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 三乙胺 、 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 四氢呋喃 、 2-甲基-1,2-丙二醇 、 二甲基亚砜 为溶剂， 反应 0.84h， 生成 3-((2-fluorothiazol-4-yl)ethynyl)benzonitrile
  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-(2-trimethylsilylethynyl)thiazol-2-amine 在 亚硝酸丁酯 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 反应 0.75h， 以30%的产率得到2-(2-chlorothiazol-4-yl)ethynyltrimethylsilane
  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

文献信息

• [EN] NOVEL GALACTOSIDE INHIBITOR OF GALECTINS<br/>[FR] NOUVEAU GALACTOSIDE COMME INHIBITEUR DE GALECTINES
  申请人：GALECTO BIOTECH AB

  公开号：WO2021001528A1

  公开（公告）日：2021-01-07

  The present invention relates to a D-galactopyranose compound of formula (1) wherein the pyranose ring is α-D-galactopyranose, and these compounds are high affinity galectin-1 and/or galectin 3 inhibitors for use in treatment of inflammation; fibrosis; scarring; keloid formation; aberrant scar formation; surgical adhesions; septic shock; cancer; metastasising cancers; autoimmune diseases, metabolic disorders; heart disease; heart failure; pathological angiogenesis; eye diseases; atherosclerosis; metabolic diseases; diabetes type I; diabetes type II; insulin resistance; Diastolic heart failure; asthma; liver disorders.

  本发明涉及一种式（1）的D-半乳糖吡喃糖类化合物，其中吡喃糖环为α-D-半乳糖吡喃糖，这些化合物是高亲和力的galectin-1和/或galectin 3抑制剂，用于治疗炎症；纤维化；瘢痕形成；瘢痕增生；异常瘢痕形成；手术粘连；脓毒性休克；癌症；转移性癌症；自身免疫疾病；代谢紊乱；心脏病；心力衰竭；病理性血管生成；眼部疾病；动脉粥样硬化；代谢性疾病；糖尿病I型；糖尿病II型；胰岛素抵抗；舒张期心力衰竭；哮喘；肝脏疾病。
• 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。
• 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.