4-Phenylethynyl-thiazole | 111600-88-5

• 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: 4-Phenylethynyl-thiazole
• 英文别名: Thiazole, 4-(phenylethynyl)-；4-(2-phenylethynyl)-1,3-thiazole
• CAS: 111600-88-5
• 化学式: C₁₁H₇NS
• 分子量: 185.249
• InChiKey: RESHTYCQJVKIMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 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

• 作为产物：
  描述：

  4-溴噻唑 、 苯乙炔 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 乙二醇二甲醚 为溶剂， 反应 5.0h， 以77%的产率得到4-Phenylethynyl-thiazole
  参考文献：
  名称：

  3-[(2-Methyl-1,3-thiazol-4-yl)ethynyl]- pyridine:  A Potent and Highly Selective Metabotropic Glutamate Subtype 5 Receptor Antagonist with Anxiolytic Activity

  摘要：

  2-Methyl-6-(phenylethynyl)pyridine (3), a potent noncompetitive mGlu5 receptor antagonist widely used to characterize the pharmacology of mGlu5 receptors, suffers from a number of shortcomings as a therapeutic agent, including off-target activity and poor aqueous solubility. Seeking to improve the properties of 3 led to the synthesis of compound 9, a highly selective mGlu5 receptor antagonist that is 5-fold more potent than 3 in the rat fear-potentiated startle model of anxiety.

  DOI：

  10.1021/jm025570j

文献信息

• Fluorination method
  申请人：Oxford University Innovation Limited

  公开号：US10287220B2

  公开（公告）日：2019-05-14

  The present invention relates to a process for producing an organic compound comprising an 18F atom. The compounds comprising an 18F can be useful as PET ligands for use in diagnostics and/or scanning. The process of the invention comprises treating an organoboron compound, which organoboron compound comprises a boron atom bonded to an sp2 hybridized carbon atom, with (i) 18F— and (ii) a copper compound. The invention also provides the use of an organoboron compound, which organoboron compound comprises a boron atom bonded to an sp2 hybridized carbon atom, in a process for producing an organic compound comprising an 18F atom, which process comprises treating the organoboron compound with (i)18F— and (ii) a copper compound. The invention also provides a compound of formula (XXXVII): wherein: each PGA is independently H or an alcohol protecting group; PGB is H or a carboxylic acid protecting group; each PGC is independently an amine protecting group; Z is a group selected from a boronic ester group, a boronic acid group, a borate group, and a trifluoroborate group; and a is an integer from 0 to 4.

  本发明涉及一种生产含有 18F 原子的有机化合物的工艺。含有 18F 的化合物可用作 PET 配体，用于诊断和/或扫描。本发明的工艺包括用(i)18F-和(ii)铜化合物处理有机硼化合物，该有机硼化合物包括与sp2杂化碳原子键合的硼原子。本发明还提供了有机硼化合物在生产包含 18F 原子的有机化合物的工艺中的用途，该有机硼化合物包含与 sp2 杂化碳原子键合的硼原子，该工艺包括用(i)18F- 和(ii)铜化合物处理该有机硼化合物。本发明还提供了式(XXXVII)的化合物： 其中：每个 PGA 独立地为 H 或醇保护基；PGB 为 H 或羧酸保护基；每个 PGC 独立地为胺保护基；Z 为选自硼酸酯基、硼酸基、硼酸盐基和三氟硼酸盐基的基团；以及 a 为 0 至 4 的整数。
• Sakamoto, Takao; Nagata, Hideo; Kondo, Yoshinori, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 2, p. 823 - 828
  作者：Sakamoto, Takao、Nagata, Hideo、Kondo, Yoshinori、Shiraiwa, Masafumi、Yamanaka, Hiroshi

  DOI：——

  日期：——
• FLUORINATION METHOD
  申请人：Oxford University Innovation Limited

  公开号：US20170137341A1

  公开（公告）日：2017-05-18

  The present invention relates to a process for producing an organic compound comprising an 18 F atom. The compounds comprising an 18 F can be useful as PET ligands for use in diagnostics and/or scanning. The process of the invention comprises treating an organoboron compound, which organoboron compound comprises a boron atom bonded to an sp 2 hybridised carbon atom, with (i) 18 F— and (ii) a copper compound. The invention also provides the use of an organoboron compound, which organoboron compound comprises a boron atom bonded to an sp 2 hybridised carbon atom, in a process for producing an organic compound comprising an 18 F atom, which process comprises treating the organoboron compound with (i) 18 F— and (ii) a copper compound. The invention also provides a compound of formula (XXXVII): wherein: each PG A is independently H or an alcohol protecting group; PG B is H or a carboxylic acid protecting group; each PG C is independently an amine protecting group; Z is a group selected from a boronic ester group, a boronic acid group, a borate group, and a trifluoroborate group; and a is an integer from 0 to 4.
• 3-[(2-Methyl-1,3-thiazol-4-yl)ethynyl]- pyridine:  A Potent and Highly Selective Metabotropic Glutamate Subtype 5 Receptor Antagonist with Anxiolytic Activity
  作者：Nicholas D. P. Cosford、Lida Tehrani、Jeffrey Roppe、Edwin Schweiger、Nicholas D. Smith、Jeffrey Anderson、Linda Bristow、Jesse Brodkin、Xiaohui Jiang、Ian McDonald、Sara Rao、Mark Washburn、Mark A. Varney

  DOI：10.1021/jm025570j

  日期：2003.1.1

  2-Methyl-6-(phenylethynyl)pyridine (3), a potent noncompetitive mGlu5 receptor antagonist widely used to characterize the pharmacology of mGlu5 receptors, suffers from a number of shortcomings as a therapeutic agent, including off-target activity and poor aqueous solubility. Seeking to improve the properties of 3 led to the synthesis of compound 9, a highly selective mGlu5 receptor antagonist that is 5-fold more potent than 3 in the rat fear-potentiated startle model of anxiety.