4-(1,3-dioxolan-2-yl)-7-iodo-2-(trifluoromethyl)pyrazolo[1,5-a]pyridine | 1010819-23-4

• 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-(1,3-dioxolan-2-yl)-7-iodo-2-(trifluoromethyl)pyrazolo[1,5-a]pyridine
• CAS: 1010819-23-4
• 化学式: C₁₁H₈F₃IN₂O₂
• 分子量: 384.096
• InChiKey: NWKHBOGWOQZUSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(1,3-dioxolan-2-yl)-7-iodo-2-(trifluoromethyl)pyrazolo[1,5-a]pyridine 在 吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 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 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 59.5h， 生成 N-(3,5-dichloropyridin-4-yl)-7-(hydroxymethyl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyridine-4-carboxamide
  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-[[(tert-butyldimethylsilyl)oxy]methyl]-7-iodo-2-(trifluoromethyl)pyrazolo[1,5-a]pyridine 在 manganese(IV) oxide 、 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 氯仿 、 水 、 甲苯 为溶剂， 反应 28.0h， 生成 4-(1,3-dioxolan-2-yl)-7-iodo-2-(trifluoromethyl)pyrazolo[1,5-a]pyridine
  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

• Pyrazolopyride derivative and phosphodiesterase ( pde) inhibitors containing the same as active ingredient
  申请人：Kohno Yasushi

  公开号：US20090318385A1

  公开（公告）日：2009-12-24

  A novel pyrazolopyridine derivative is provided which is useful as a pharmaceutical drug having phosphodiesterase inhibitory activity. The pyrazolopyridine derivative is represented by the following general formula (1): [wherein R 1 is a hydrogen atom, an optionally substituted alkyl group having 1 to 6 carbon atoms, or the like, R 2 is an optionally substituted alkyl group having 1 to 6 carbon atoms or the like, R 5 and R 6 are independently a hydrogen atom or a halogen atom, R 13 is a hydrogen atom or a halogen atom, n is 0 or 1, is a single or double bond, R 3 is a hydrogen atom, a hydroxyl group, or the like, and R 4 is a hydrogen atom, a phenyl group, or the like] or a pharmaceutically acceptable salt thereof, and a hydrate thereof.

  提供了一种新的吡唑吡啶衍生物，其可用作具有磷酸二酯酶抑制活性的药物。该吡唑吡啶衍生物由以下通式（1）表示：[其中，R1是氢原子、1至6个碳原子的可选取代烷基或类似物，R2是1至6个碳原子的可选取代烷基或类似物，R5和R6独立地是氢原子或卤素原子，R13是氢原子或卤素原子，n为0或1，为单键或双键，R3是氢原子、羟基或类似物，R4是氢原子、苯基或类似物]或其药学上可接受的盐和水合物。
• 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：——
• EP2060572
  申请人：——

  公开号：——

  公开（公告）日：——