[7-methoxy-2-(trifluoromethyl)pyrazolo[1,5-a]pyridin-4-yl](pyridin-4-yl)methanol | 1454802-92-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: [7-methoxy-2-(trifluoromethyl)pyrazolo[1,5-a]pyridin-4-yl](pyridin-4-yl)methanol
• 英文别名: [7-Methoxy-2-(trifluoromethyl)pyrazolo[1,5-a]pyridin-4-yl]-pyridin-4-ylmethanol；[7-methoxy-2-(trifluoromethyl)pyrazolo[1,5-a]pyridin-4-yl]-pyridin-4-ylmethanol
• CAS: 1454802-92-6
• 化学式: C₁₅H₁₂F₃N₃O₂
• 分子量: 323.274
• InChiKey: PCHJMMCRUACMBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [7-methoxy-2-(trifluoromethyl)pyrazolo[1,5-a]pyridin-4-yl](pyridin-4-yl)methanol 在 三氧化硫吡啶 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以85%的产率得到[7-methoxy-2-(trifluoromethyl)pyrazolo[1,5-a]pyridin-4-yl](pyridin-4-yl)methanone
  参考文献：
  名称：

  Phosphodiesterase inhibitors. Part 6: Design, synthesis, and structure–activity relationships of PDE4-inhibitory pyrazolo[1,5-a]pyridines with anti-inflammatory activity

  摘要：

  We previously identified KCA-1490 [(-)-6-(7-methoxy-2-trifluoromethyl-pyrazolo[1,5-alpha] pyridin-4-yl)-5- methyl-4,5-dihydro-3-(2H)-pyridazinone], a dual PDE3/4 inhibitor. In the present study, we found highly potent selective PDE4 inhibitors derived from the structure of KCA-1490. Among them, N-(3,5-dichloropyridin-4-yl)-7-methoxy-2-(trifluoromethyl) pyrazolo[1,5-alpha] pyridine-4-carboxamide (2 alpha) had good anti-inflammatory effects in an animal model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.069
• 作为产物：
  描述：

  (6-甲氧基吡啶-3-基)甲醇 在 manganese(IV) oxide 、 异丙基氯化镁 、 2,4,6-三甲基苯磺酰羟胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 邻二氯苯 为溶剂， 反应 27.5h， 生成 [7-methoxy-2-(trifluoromethyl)pyrazolo[1,5-a]pyridin-4-yl](pyridin-4-yl)methanol
  参考文献：
  名称：

  Phosphodiesterase inhibitors. Part 6: Design, synthesis, and structure–activity relationships of PDE4-inhibitory pyrazolo[1,5-a]pyridines with anti-inflammatory activity

  摘要：

  We previously identified KCA-1490 [(-)-6-(7-methoxy-2-trifluoromethyl-pyrazolo[1,5-alpha] pyridin-4-yl)-5- methyl-4,5-dihydro-3-(2H)-pyridazinone], a dual PDE3/4 inhibitor. In the present study, we found highly potent selective PDE4 inhibitors derived from the structure of KCA-1490. Among them, N-(3,5-dichloropyridin-4-yl)-7-methoxy-2-(trifluoromethyl) pyrazolo[1,5-alpha] pyridine-4-carboxamide (2 alpha) had good anti-inflammatory effects in an animal model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.069