2-fluoro-3-[5-methyl-4-(tributylstannyl)-1H-1,2,3-triazol-1-yl]pyridine | 864866-09-1

• 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
• 英文名称: 2-fluoro-3-[5-methyl-4-(tributylstannyl)-1H-1,2,3-triazol-1-yl]pyridine
• 英文别名: 1-(2-fluoro-3-pyridyl)-5-methyl-4-(tri-n-butylstannyl)-1H-1,2,3-triazole；1-(2-fluoropyridine-3-yl)-5-methyl-4-tributylstanyl-1H-[1,2,3]triazole；tributyl-[1-(2-fluoropyridin-3-yl)-5-methyltriazol-4-yl]stannane
• CAS: 864866-09-1
• 化学式: C₂₀H₃₃FN₄Sn
• 分子量: 467.217
• InChiKey: MHCOLAOHGYHHRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-fluoro-3-[5-methyl-4-(tributylstannyl)-1H-1,2,3-triazol-1-yl]pyridine 在 四(三苯基膦)钯 甲酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 10.0h， 生成 4-(2-cyclopropyl-1-oxo-isoindoline-5-yl)-1-(2-methoxypyridine-3-yl)-5-methyl-1H-[1,2,3]triazole
  参考文献：
  名称：

  EP1726585

  摘要：

  公开号：
• 作为产物：
  描述：

  2-氟吡啶 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 3.25h， 生成 2-fluoro-3-[5-methyl-4-(tributylstannyl)-1H-1,2,3-triazol-1-yl]pyridine
  参考文献：
  名称：

  EP1726585

  摘要：

  公开号：

文献信息

• Discovery and biological profile of 4-(1-aryltriazol-4-yl)-tetrahydropyridines as an orally active new class of metabotropic glutamate receptor 1 antagonist
  作者：Satoru Ito、Atsushi Satoh、Yasushi Nagatomi、Yukari Hirata、Gentaroh Suzuki、Toshifumi Kimura、Akio Satow、Shunsuke Maehara、Hirohiko Hikichi、Mikiko Hata、Hiroshi Kawamoto、Hisashi Ohta

  DOI：10.1016/j.bmc.2008.09.060

  日期：2008.11

  We describe here the discovery and the structure-activity relationship (SAR) of a series of 4-(1-Aryl-triazol-4- yl)-tetrahydropyridines as novel mGluR1 antagonists. Our extensive chemical modi. cation of lead compound 2 successfully led to fluoropyridine analogs 7j and 1 with improved in vivo antagonistic activities. Among the evaluated compounds, chemically stable urea analog 1 showed oral antagonistic activity at dose ranges of 10-30 mg/kg in an animal model. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of 6-[1-(2-[18F]fluoro-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline for positron emission tomography imaging of the metabotropic glutamate receptor type 1 in brain
  作者：Masayuki Fujinaga、Tomoteru Yamasaki、Kazunori Kawamura、Katsushi Kumata、Akiko Hatori、Joji Yui、Kazuhiko Yanamoto、Yuichiro Yoshida、Masanao Ogawa、Nobuki Nengaki、Jun Maeda、Toshimitsu Fukumura、Ming-Rong Zhang

  DOI：10.1016/j.bmc.2010.11.048

  日期：2011.1

  The purpose of this study was to synthesize 6-[1-(2-[F-18]fluoro-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline ([F-18]FPTQ, [F-18]7a) and to evaluate its potential as a positron emission tomography ligand for imaging metabotropic glutamate receptor type 1 (mGluR1) in the rat brain. Compound [F-18]7a was synthesized by [F-18] fluorination of 6-[1-(2-bromo-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl] quinoline (7b) with potassium [F-18] fluoride. At the end of synthesis, 1280-1830 MBq (n = 8) of [F-18]7a was obtained with >98% radiochemical purity and 118-237 GBq/mu mol specific activity using 3300-4000 MBq of [F-18]F . In vitro autoradiography showed that [F-18]7a had high specific binding with mGluR1 in the rat brain. Biodistribution study using a dissection method and small-animal PET showed that [F-18]7a had high uptake in the rat brain. The uptake of radioactivity in the cerebellum was reduced by unlabeled 7a and mGluR1-selective ligand JNJ-16259685 (2), indicating that [F-18]7a had in vivo specific binding with mGluR1. Because of a low amount of radiolabeled metabolite present in the brain, [F-18]7a may have a limiting potential for the in vivo imaging of mGluR1 by PET. (C) 2010 Elsevier Ltd. All rights reserved.
• Discovery and biological profile of isoindolinone derivatives as novel metabotropic glutamate receptor 1 antagonists: A potential treatment for psychotic disorders
  作者：Satoru Ito、Yukari Hirata、Yasushi Nagatomi、Atsushi Satoh、Gentaroh Suzuki、Toshifumi Kimura、Akio Satow、Shunsuke Maehara、Hirohiko Hikichi、Mikiko Hata、Hisashi Ohta、Hiroshi Kawamoto

  DOI：10.1016/j.bmcl.2009.07.145

  日期：2009.9

  We describe here the discovery and biological profile of a series of isoindolinone derivatives as developed mGluR1 antagonists. Our combined strategy of rapid parallel synthesis and conventional medicinal optimization successfully led to N-cyclopropyl 22 and N-isopropyl isoindolinone analogs 21 and 23 with improved in vivo DMPK profiles. Moreover the most advanced analog 23 showed an oral antipsychotic-like effect at a dose of 1 mg/kg in an animal model. (C) 2009 Elsevier Ltd. All rights reserved.
• EP1726585
  申请人：——

  公开号：——

  公开（公告）日：——