(RS)-2-(2,6-dioxopiperidin-3-yl)-4-(3-hydroxy-3-methylbut-1-ynyl)isoindoline-1,3-dione | 1216805-62-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (RS)-2-(2,6-dioxopiperidin-3-yl)-4-(3-hydroxy-3-methylbut-1-ynyl)isoindoline-1,3-dione
• 英文别名: 2-(2,6-Dioxopiperidin-3-yl)-4-(3-hydroxy-3-methylbut-1-ynyl)isoindole-1,3-dione
• CAS: 1216805-62-7
• 化学式: C₁₈H₁₆N₂O₅
• 分子量: 340.335
• InChiKey: SMUDUKXKVDMYFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(2,6-dioxopiperidin-3-yl)-4-iodoisoindoline-1,3-dione 、 2-甲基-3-丁炔-2-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到(RS)-2-(2,6-dioxopiperidin-3-yl)-4-(3-hydroxy-3-methylbut-1-ynyl)isoindoline-1,3-dione
  参考文献：
  名称：

  New thalidomide analogues derived through Sonogashira or Suzuki reactions and their TNF expression inhibition profiles

  摘要：

  A library of new thalidomide C4/5 analogues containing either a phenyl or alkyne tether were synthesized using Sonogashira or Suzuki cross coupling reactions from their aryl halogenated precursors. All thalidomide analogues were tested for their ability to inhibit the expression of the proinflammatory cytokine Tumor Necrosis Factor (TNF). More explicitly the use of a novel reporter system utilizing the promoter region of the TNF gene in a human T-cell line provided a rapid and effective measure of NF kappa B transcriptional activity. Several compounds either containing either an aryl-isobutyl or aryl-isopropoxy group were the most effective in inhibiting TNF expression, and were several times more active than thalidomide itself. Five of the more active derivatives indicated an apoptotic response while one of these compounds, containing an aldehyde tether, showed possible influence of cell cycling effects. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.001

文献信息

• New thalidomide analogues derived through Sonogashira or Suzuki reactions and their TNF expression inhibition profiles
  作者：Scott G. Stewart、Carlos J. Braun、Sze-Ling Ng、Marta E. Polomska、Mahdad Karimi、Lawrence J. Abraham

  DOI：10.1016/j.bmc.2009.12.001

  日期：2010.1

  A library of new thalidomide C4/5 analogues containing either a phenyl or alkyne tether were synthesized using Sonogashira or Suzuki cross coupling reactions from their aryl halogenated precursors. All thalidomide analogues were tested for their ability to inhibit the expression of the proinflammatory cytokine Tumor Necrosis Factor (TNF). More explicitly the use of a novel reporter system utilizing the promoter region of the TNF gene in a human T-cell line provided a rapid and effective measure of NF kappa B transcriptional activity. Several compounds either containing either an aryl-isobutyl or aryl-isopropoxy group were the most effective in inhibiting TNF expression, and were several times more active than thalidomide itself. Five of the more active derivatives indicated an apoptotic response while one of these compounds, containing an aldehyde tether, showed possible influence of cell cycling effects. (C) 2009 Elsevier Ltd. All rights reserved.