2-乙炔基-6-氟吡啶 | 1233205-73-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-乙炔基-6-氟吡啶
• 中文别名: 2-乙炔-6-氟吡啶
• 英文名称: 2-ethynyl-6-fluoropyridine
• CAS: 1233205-73-6
• 化学式: C₇H₄FN
• 分子量: 121.114
• InChiKey: JFEWFXHNPSMINO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-乙炔基-6-氟吡啶 、 1-amino-4-cyanopyridinium 2,4,6-trimethylbenzenesulfonate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以45%的产率得到5-cyano-3-(6-fluoropyridin-2-yl)pyrazolo[1,5-a]pyridine
  参考文献：
  名称：

  [EN] PYRAZOLE[1,5a]PYRIDINE DERIVATIVES
  [FR] DÉRIVÉS DE PYRAZOLE[1,5A]PYRIDINE

  摘要：

  式I的吡唑并[1,5-a]吡啶衍生物，其中R1、R2和R3的含义如描述中所披露的。这些化合物可用作JAK3激酶抑制剂。

  公开号：

  WO2010072823A1
• 作为产物：
  描述：

  2-((tert-butyldimethylsilyl)ethynyl)-6-fluoropyridine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2-乙炔基-6-氟吡啶
  参考文献：
  名称：

  Efficient ¹⁸F-Labeling of Large 37-Amino-Acid pHLIP Peptide Analogues and Their Biological Evaluation

  摘要：

  Solid tumors often develop an acidic microenvironment, which plays a critical role in tumor progression and is associated with increased level of invasion and metastasis. The 37 residue pH (low) insertion peptide (pHLIP) is under study as an imaging platform because of its Unique ability to insert into cell membranes at a low extracellular pH (pH(e) < 7). Labeling of peptides with [F-18] fluorine is usually performed via prosthetic groups using chemoselective coupling reactions. One of the most successful procedures involves the alkyne-azide copper(I) catalyzed cydoaddition (CuAAC). However, none of the known "click" methods have been applied to peptides as large as pHLIP. We designed a novel prosthetic group and extended the use of the CuAAC "click chemistry" for the simple and efficient F-18 labeling of large peptides. For the evaluation of this labeling approach, a D-amino acid analogue of WT-pHLIP and an L-amino acid control peptide K-pHLIP, both functionalized at the N-terminus with 6-azidohexanoic acid, were used. The novel 6-[F-18]fluoro-2-ethynylpyridine prosthetic group, was obtained via nucleophilic substitution on the corresponding bromo-precursor after 10 mm at 130 C with a radiochemical yield of 27.5 +/- 6.6% (decay corrected) with high radiochemical purity >= 98%. The subsequent Cu-I-catalyzed "click" reaction with the azido functionalized pHLIP peptides was quantitative within 5 min at 70 C in a mixture of water and ethanol using Cu acetate and sodium L-ascorbate. j D-WT-pHLIP and [F-18]-L-K-pHLIP were obtained with total radiochemical yields of 5-20% after HPLC purification. The total reaction time was 85 min including formulation. In vitro stability tests revealed high stability of the [F-18]-6-WT-pHLIP in human and mouse plasma after 120 mm, with the parent tracer remaining intact at 65% and 85%, respectively. PET imaging and biodistribution studies in LNCaP and PC -3 xenografted mice with the [F-18]-6-WT-pHLIP and the negative control [F-18]-L-K-pHLIP revealed pH dependent tumor retention. This reliable and efficient protocol promises to be useful for the F-18 labeling of large peptides such as pHLIP and will accelerate the evaluation of numerous [F-15]-pHLIP analogues as potential PET tracers.

  DOI：

  10.1021/bc3000222

文献信息

• [EN] OXAZOLIDINONES AS MODULATORS OF MGLUR5<br/>[FR] OXAZOLIDINONES EN TANT QUE MODULATEURS DE MGLUR5
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2012064603A1

  公开（公告）日：2012-05-18

  The disclosure generally relates to compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds are ligands, agonists and partial agonists for the mGluR5 receptor and may be useful for the treatment of various disorders of the central nervous system.

  该披露通常涉及到公式I的化合物，包括它们的盐，以及使用这些化合物的组合物和方法。这些化合物是mGluR5受体的配体、激动剂和部分激动剂，可能对中枢神经系统的各种疾病的治疗有用。
• Compounds for Treating Disorders Mediated by Metabotropic Glutamate Receptor 5, and Methods of Use Thereof
  申请人：Hardy Larry Wendell

  公开号：US20110319380A1

  公开（公告）日：2011-12-29

  Provided herein are compounds and methods of synthesis thereof. The compounds set forth herein are useful for the treatment, prevention, and/or management of various disorders, such as neurological disorders, neurodegenerative disorders, neuropsychiatric disorders, disorders of cognition, learning or memory, gastrointestinal disorders, lower urinary tract disorder, and cancer. Compounds set forth herein modulate the activity of metabotropic glutamate receptor 5 (mGluR5) in the central nervous system or the periphery. Pharmaceutical formulations containing the compounds and their methods of use are also provided herein.

  本文提供了化合物及其合成方法。本文中提供的化合物可用于治疗、预防和/或管理各种疾病，如神经系统疾病、神经退行性疾病、神经精神疾病、认知、学习或记忆障碍、胃肠道疾病、下尿路障碍和癌症。本文提供的化合物在中枢神经系统或外周调节代谢性谷氨酸受体5(mGluR5)的活性。本文还提供了含有这些化合物的药物制剂及其使用方法。
• METABOTROPHIC GLUTAMATE RECEPTOR 5 MODULATORS AND METHODS OF USE THEREOF
  申请人：Heffernan Michele L. R.

  公开号：US20140179682A1

  公开（公告）日：2014-06-26

  Compounds that modulate GluR5 activity and methods of using the same are disclosed.

  本发明揭示了调节GluR5活性的化合物及其使用方法。
• COMPOUNDS FOR TREATING DISORDERS MEDIATED BY METABOTROPIC GLUTAMATE RECEPTOR 5, AND METHODS OF USE THEREOF
  申请人：Sunovion Pharmaceuticals Inc.

  公开号：US20140349992A1

  公开（公告）日：2014-11-27

  Provided herein are compounds and methods of synthesis thereof. The compounds set forth herein are useful for the treatment, prevention, and/or management of various disorders, such as neurological disorders, neurodegenerative disorders, neuropsychiatric disorders, disorders of cognition, learning or memory, gastrointestinal disorders, lower urinary tract disorder, and cancer. Compounds set forth herein modulate the activity of metabotropic glutamate receptor 5 (mGluR5) in the central nervous system or the periphery. Pharmaceutical formulations containing the compounds and their methods of use are also provided herein.

  本文提供了化合物及其合成方法。这些化合物可用于治疗、预防和/或管理各种疾病，如神经疾病、神经退行性疾病、神经精神疾病、认知、学习或记忆障碍、胃肠道疾病、下尿路障碍和癌症等。本文提供的化合物在中枢神经系统或外周调节代谢性谷氨酸受体5 (mGluR5) 的活性。本文还提供了含有这些化合物的药物制剂及其使用方法。
• Glycomimetic ligands block the interaction of SARS-CoV-2 spike protein with C-type lectin co-receptors
  作者：Sara Pollastri、Clara Delaunay、Michel Thépaut、Franck Fieschi、Anna Bernardi

  DOI：10.1039/d2cc00121g

  日期：——

  DC-SIGN and its analogue L-SIGN work as co-receptors in many viral infections, including by SARS-CoV-2. Here we describe the first group of small-molecule glycomimetics that bind to L-SIGN, as well as to DC-SIGN, with micromolar affinity.

  DC-SIGN和其类似物L-SIGN在许多病毒感染中作为共受体，包括SARS-CoV-2。在这里，我们描述了第一组与L-SIGN以及DC-SIGN具有微摩尔亲和力的小分子糖类似物的群体。