2-(2-([1,1'-biphenyl]-4-carbonyl)-1H-pyrrol-1-yl)acetic acid | 1449787-53-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-([1,1'-biphenyl]-4-carbonyl)-1H-pyrrol-1-yl)acetic acid
• 英文别名: 2-[2-(4-Phenylbenzoyl)pyrrol-1-yl]acetic acid；2-[2-(4-phenylbenzoyl)pyrrol-1-yl]acetic acid
• CAS: 1449787-53-4
• 化学式: C₁₉H₁₅NO₃
• 分子量: 305.333
• InChiKey: BHGADYQNGVDASH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 2-(2-([1,1'-biphenyl]-4-carbonyl)-1H-pyrrol-1-yl)acetate 在 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以92%的产率得到2-(2-([1,1'-biphenyl]-4-carbonyl)-1H-pyrrol-1-yl)acetic acid
  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.