tert-butyl 4-[1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl]-3,6-dihydropyridine-1(2H)-carboxylate | 873551-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl 4-[1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl]-3,6-dihydropyridine-1(2H)-carboxylate
• 英文别名: tert-Butyl 4-[1-(2-fluorophenyl)-1H-[1,2,3]triazol-4-yl]-1,2,3,6-tetrahydropyridine-1-carboxylate；tert-Butyl-4-[1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl]-3,6-dihydropyridine-1(2H)-carboxylate；tert-butyl 4-[1-(2-fluorophenyl)triazol-4-yl]-3,6-dihydro-2H-pyridine-1-carboxylate
• CAS: 873551-76-9
• 化学式: C₁₈H₂₁FN₄O₂
• 分子量: 344.389
• InChiKey: GFWSBYBQNHQKCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-[1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl]-3,6-dihydropyridine-1(2H)-carboxylate 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 0.33h， 生成 4-[1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  Discovery and biological profile of 4-(1-aryltriazol-4-yl)-tetrahydropyridines as an orally active new class of metabotropic glutamate receptor 1 antagonist

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2008.09.060
• 作为产物：
  描述：

  1-(2-fluorophenyl)-4-iodo-1H-1,2,3-triazole 、 N-Boc-1,2,5,6-四氢吡啶-4-硼酸频哪醇酯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以51 mg的产率得到tert-butyl 4-[1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl]-3,6-dihydropyridine-1(2H)-carboxylate
  参考文献：
  名称：

  Discovery and biological profile of 4-(1-aryltriazol-4-yl)-tetrahydropyridines as an orally active new class of metabotropic glutamate receptor 1 antagonist

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2008.09.060

文献信息

• Biaryl derivatives
  申请人：Kawamoto Hiroshi

  公开号：US20070191389A1

  公开（公告）日：2007-08-16

  The present invention relates to a compound represented by the formula (I): or a pharmaceutically acceptable salt thereof, wherein: R 1 is a linear or branched alkoxy group, a cycloalkoxy group, a linear or branched lower alkyl group, etc.; R 2 is halogen atom, a lower alkyl group, etc.; Q 1 is carbon atom or nitrogen atom; Q 2 is carbon atom which may be substituted with oxo group; the formula (III): (II) is a single bond or a double bond; A is a group selected from the group consisting of the substitutent group α; and R 5 is hydrogen atom, a lower alkyl group, cyano group, an alkoxy group or a trialkylsilyl group; having an mGluR1 inhibiting action and being useful as treatment and/or prevention of convulsion, acute pain, cerebral disturbance such as cerebral infarction or transient cerebral ischemia onset, anxiety, chemical dependency or Parkinson's disease.

  本发明涉及一种由以下式（I）表示的化合物或其药学上可接受的盐，其中： R1是线性或支链烷氧基，环烷氧基，线性或支链低烷基等； R2是卤素原子，低烷基等； Q1是碳原子或氮原子； Q2是可能被氧代基取代的碳原子； 式（III）： （II）是单键或双键； A是从取代基α组成的组中选择的一组；以及 R5是氢原子，低烷基，氰基，烷氧基或三烷基硅基； 具有mGluR1抑制作用，可用于治疗和/或预防抽搐，急性疼痛，脑功能障碍，如脑梗死或短暂性脑缺血发作，焦虑，化学依赖或帕金森病。
• US7858800B2
  申请人：——

  公开号：US7858800B2

  公开（公告）日：2010-12-28