(1-(1-hydroxy-1H-pyrazol-4-yl)-1H-pyrrol-2-yl)(4-methoxyphenyl)methanone | 1449787-51-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1-(1-hydroxy-1H-pyrazol-4-yl)-1H-pyrrol-2-yl)(4-methoxyphenyl)methanone
• 英文别名: [1-(1-Hydroxypyrazol-4-yl)pyrrol-2-yl]-(4-methoxyphenyl)methanone；[1-(1-hydroxypyrazol-4-yl)pyrrol-2-yl]-(4-methoxyphenyl)methanone
• CAS: 1449787-51-2
• 化学式: C₁₅H₁₃N₃O₃
• 分子量: 283.287
• InChiKey: VYNLJRDBKHRAEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(benzyloxy)-4-(1H-pyrrol-1-yl)-1H-pyrazole 在 aluminum (III) chloride 、 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 12.0h， 生成 (1-(1-hydroxy-1H-pyrazol-4-yl)-1H-pyrrol-2-yl)(4-methoxyphenyl)methanone
  参考文献：
  名称：

  1-Hydroxypyrazole as a bioisostere of the acetic acid moiety in a series of aldose reductase inhibitors

  摘要：

  Therapeutic intervention with aldose reductase inhibitors appears to be promising for major pathological conditions (i.e., long-term diabetic complications and inflammatory pathologies). So far, however, clinical candidates have failed due to adverse side-effects (spiroimides) or poor bioavailability (carboxylic acids). In this work, we succeeded in the bioisosteric replacement of an acetic acid moiety with that of 1-hydroxypyrazole. This new scaffold appears to have a superior physicochemical profile, while attaining inhibitory activity in the submicromolar range. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.062

文献信息

• 1-Hydroxypyrazole as a bioisostere of the acetic acid moiety in a series of aldose reductase inhibitors
  作者：Nikolaos Papastavrou、Maria Chatzopoulou、Kyriaki Pegklidou、Ioannis Nicolaou

  DOI：10.1016/j.bmc.2013.06.062

  日期：2013.9

  Therapeutic intervention with aldose reductase inhibitors appears to be promising for major pathological conditions (i.e., long-term diabetic complications and inflammatory pathologies). So far, however, clinical candidates have failed due to adverse side-effects (spiroimides) or poor bioavailability (carboxylic acids). In this work, we succeeded in the bioisosteric replacement of an acetic acid moiety with that of 1-hydroxypyrazole. This new scaffold appears to have a superior physicochemical profile, while attaining inhibitory activity in the submicromolar range. (C) 2013 Elsevier Ltd. All rights reserved.