[4-[(3,5-dichloropyridin-4-yl)carbamoyl]-2-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl]methyl acetate | 1009602-84-9

• 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: [4-[(3,5-dichloropyridin-4-yl)carbamoyl]-2-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl]methyl acetate
• 英文别名: 7-Acetoxymethyl-2-trifluoromethylpyrazolo[1,5-a]pyridine-4-carboxylic acid (3,5-dichloropyridin-4-yl)amide
• CAS: 1009602-84-9
• 化学式: C₁₇H₁₁Cl₂F₃N₄O₃
• 分子量: 447.201
• InChiKey: OWYQUSXNOCQAQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  85.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [4-[(3,5-dichloropyridin-4-yl)carbamoyl]-2-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl]methyl acetate 在 三氧化硫吡啶 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 12.17h， 生成 N-(3,5-二氯吡啶-4-基)-7-(1-羟乙基)-2-(三氟甲基)吡唑并[1,5-a]吡啶-4-甲酰胺
  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：

  4-(1,3-dioxolan-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyridine-7-carbaldehyde 在 吡啶 、 sodium tetrahydroborate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 红铝 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 53.5h， 生成 [4-[(3,5-dichloropyridin-4-yl)carbamoyl]-2-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl]methyl acetate
  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

文献信息

• Pyrazolopyridine carboxamide derivative and phosphodiesterase (pde) inhibitor containing the same
  申请人：Kohno Yasushi

  公开号：US20100056791A1

  公开（公告）日：2010-03-04

  A novel pyrazolopyridine carboxamide derivative is provided that is useful as a pharmaceutical drug having phosphodiesterase inhibitory activity. The pyrazolopyridine carboxamide derivative is represented by the following general formula (1): (Example: 2-ethyl-7-methoxypyrazolo[1,5-a]pyridine-4-carboxylic acid (3,5-dichloropyridin-4-yl)amide).

  提供了一种新型的吡唑吡啶羧酰胺衍生物，其可用作具有磷酸二酯酶抑制活性的药物。该吡唑吡啶羧酰胺衍生物由以下通式（1）表示：（例如：2-乙基-7-甲氧基吡唑并[1,5-a]吡啶-4-羧酸（3,5-二氯吡啶-4-基）酰胺）。
• EP2058310
  申请人：——

  公开号：——

  公开（公告）日：——