2-ethyl-7-methoxypyrazolo[1,5-a]pyridine-4-carboxylic acid 4-nitrophenyl ester | 1009601-48-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-ethyl-7-methoxypyrazolo[1,5-a]pyridine-4-carboxylic acid 4-nitrophenyl ester
• 英文别名: (4-nitrophenyl) 2-ethyl-7-methoxypyrazolo[1,5-a]pyridine-4-carboxylate
• CAS: 1009601-48-2
• 化学式: C₁₇H₁₅N₃O₅
• 分子量: 341.323
• InChiKey: NHDHOMMZKCZSFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 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：
  98.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-氨基-3,5-二氯吡啶 、 2-ethyl-7-methoxypyrazolo[1,5-a]pyridine-4-carboxylic acid 4-nitrophenyl ester 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 N-(3,5-二氯吡啶-4-基)-2-乙基-7-甲氧基吡唑并[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：

  ethyl 2-ethyl-4-hydroxymethyl-7-methoxypyrazolo[1,5-a]pyridine-3-carboxylate 在 4-二甲氨基吡啶 、 manganese(IV) oxide 、 sodium chlorite 、 2-甲基-2-丁烯 、 sodium dihydrogenphosphate dihydrate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 邻二氯苯 、 叔丁醇 为溶剂， 反应 31.0h， 生成 2-ethyl-7-methoxypyrazolo[1,5-a]pyridine-4-carboxylic acid 4-nitrophenyl ester
  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）。
• PYRAZOLOPYRIDINE CARBOXAMIDE DERIVATIVE AND PHOSPHODIESTERASE (PDE) INHIBITOR COMPRISING THE DERIVATIVE
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：EP2058310A1

  公开（公告）日：2009-05-13

  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).

  本研究提供了一种新型吡唑吡啶羧酰胺衍生物，可用作具有磷酸二酯酶抑制活性的药物。 吡唑吡啶羧酰胺衍生物由以下通式（1）表示： (例：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：——