2-(2,6-dioxopiperidin-3-yl)-5-phenylisoindoline-1,3-dione | 1216805-49-0

• 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: 2-(2,6-dioxopiperidin-3-yl)-5-phenylisoindoline-1,3-dione
• 英文别名: (RS)-2-(2,6-dioxopiperidin-3-yl)-5-phenylisoindole-1,3-dione；2-(2,6-dioxopiperidin-3-yl)-5-phenylisoindole-1,3-dione
• CAS: 1216805-49-0
• 化学式: C₁₉H₁₄N₂O₄
• 分子量: 334.331
• InChiKey: YKPRLSWMWNNOOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,2-二甲基-3-碘苯 在 吡啶 、 potassium permanganate 、 [Pd₂(dba)₃]*CHCl₃ 、 potassium carbonate 、 三乙胺 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 136.0h， 生成 2-(2,6-dioxopiperidin-3-yl)-5-phenylisoindoline-1,3-dione
  参考文献：
  名称：

  In pursuit of a selective hepatocellular carcinoma therapeutic agent: Novel thalidomide derivatives with antiproliferative, antimigratory and STAT3 inhibitory properties

  摘要：

  DOI：

  10.1016/j.ejmech.2021.113353

文献信息

• Anhydrous and Stereoretentive Fluoride-Enhanced Suzuki–Miyaura Coupling of Immunomodulatory Imide Drug Derivatives
  作者：William F. Tracy、Geraint H. M. Davies、Lauren N. Grant、Jacob M. Ganley、Jesus Moreno、Emily C. Cherney、Huw M. L. Davies

  DOI：10.1021/acs.joc.3c02873

  日期：2024.4.5

  Immunomodulatory imide drugs form the core of many pharmaceutically relevant structures, but Csp2–Csp2 bond formation via metal-catalyzed cross coupling is difficult due to the sensitivity of the glutarimide ring ubiquitous in these structures. We report that replacement of the traditional alkali base with a fluoride source enhances a previously challenging Suzuki–Miyaura coupling on glutarimide-containing

  免疫调节酰亚胺药物形成了许多药学相关结构的核心，但由于这些结构中普遍存在的戊二酰亚胺环的敏感性，通过金属催化交叉偶联形成 C sp 2 –C sp 2键很困难。我们报告说，用氟化物源替代传统的碱基增强了先前具有挑战性的含戊二酰亚胺化合物与三氟硼酸盐的铃木-宫浦偶联。这些有利条件的反应性足以以高产率生成这些衍生物，但又足够温和以保留戊二酰亚胺及其敏感的立体中心。实验和计算数据表明，在这些条件下，三氟硼酸盐发生了机械上不同的 π 配位过程。
• 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.
• Proteolysis-targeting chimeras with reduced off-targets
  作者：Tuan M. Nguyen、Vedagopuram Sreekanth、Arghya Deb、Praveen Kokkonda、Praveen K. Tiwari、Katherine A. Donovan、Veronika Shoba、Santosh K. Chaudhary、Jaron A. M. Mercer、Sophia Lai、Ananthan Sadagopan、Max Jan、Eric S. Fischer、David R. Liu、Benjamin L. Ebert、Amit Choudhary

  DOI：10.1038/s41557-023-01379-8

  日期：2024.2
• In pursuit of a selective hepatocellular carcinoma therapeutic agent: Novel thalidomide derivatives with antiproliferative, antimigratory and STAT3 inhibitory properties
  作者：Michael J. Nutt、Yeung Sing Yee、Amanda Buyan、Neil Andrewartha、Ben Corry、George C.T. Yeoh、Scott G. Stewart

  DOI：10.1016/j.ejmech.2021.113353

  日期：2021.5