(R)-3-(3,4-Dimethoxy-phenyl)-3-(4,5,6,7-tetrafluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-3-(3,4-Dimethoxy-phenyl)-3-(4,5,6,7-tetrafluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester
• 英文别名: methyl (3R)-3-(3,4-dimethoxyphenyl)-3-(4,5,6,7-tetrafluoro-1,3-dioxoisoindol-2-yl)propanoate
• 化学式: C₂₀H₁₅F₄NO₆
• 分子量: 441.336
• InChiKey: AQCHRLTWCAURNI-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3,4,5,6-四氟苯酐 、 methyl (3R)-3-amino-3-(3,4-dimethoxyphenyl)propanoate 生成 (R)-3-(3,4-Dimethoxy-phenyl)-3-(4,5,6,7-tetrafluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Enhanced potency of perfluorinated thalidomide derivatives for inhibition of LPS-induced tumor necrosis factor-α production is associated with a change of mechanism of action

  摘要：

  Perfluorination of phthalimides leads to dramatically increased potency as inhibitors of TNF-alpha production. We examined the enantiodependence for several tetrafluorophthalimides and alpha-methylthalidomide, 3. Only 3 exhibited strikingly enantiodependent activity. The key structural determinant for the enhanced activity is the tetrafluorophthaloyl group, which confers enhanced potency and a change in the mechanism of inhibition. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00171-1

文献信息

• Enhanced potency of perfluorinated thalidomide derivatives for inhibition of LPS-induced tumor necrosis factor-α production is associated with a change of mechanism of action
  作者：Satomi Niwayama、Christine Loh、Benjamin E. Turk、Jun O. Liu、Hiroyuki Miyachi、Yuichi Hashimoto

  DOI：10.1016/s0960-894x(98)00171-1

  日期：1998.5

  Perfluorination of phthalimides leads to dramatically increased potency as inhibitors of TNF-alpha production. We examined the enantiodependence for several tetrafluorophthalimides and alpha-methylthalidomide, 3. Only 3 exhibited strikingly enantiodependent activity. The key structural determinant for the enhanced activity is the tetrafluorophthaloyl group, which confers enhanced potency and a change in the mechanism of inhibition. (C) 1998 Elsevier Science Ltd. All rights reserved.