(RS)-5-(3,3-dimethylbut-1-ynyl)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione | 1216805-29-6

• 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)-5-(3,3-dimethylbut-1-ynyl)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
• 英文别名: 5-(3,3-Dimethylbut-1-ynyl)-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione
• CAS: 1216805-29-6
• 化学式: C₁₉H₁₈N₂O₄
• 分子量: 338.363
• InChiKey: JEHNSDQFACEPPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  535-溴-2-（26-二氧哌啶-3-基）异吲哚啉-13-二酮 、 3,3-二甲基-1-丁炔 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， 反应 18.0h， 以76%的产率得到(RS)-5-(3,3-dimethylbut-1-ynyl)-2-(2,6-dioxopiperidin-3-yl)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

• MITOGEN-ACTIVATED PROTEIN KINASE KINASE (MEK) DEGRADATION COMPOUNDS AND METHODS OF USE
  申请人：Icahn School of Medicine at Mount Sinai

  公开号：US20210395244A1

  公开（公告）日：2021-12-23

  This disclosure relates to heterobifunctional compounds (e.g., bi-functional small molecule compounds), compositions comprising one or more of the heterobifunctional compounds, and to methods of use the heterobifunctional compounds for the treatment of certain disease in a subject in need thereof. The disclosure also relates to methods for identifying such heterobifunctional compounds.

  该披露涉及异双功能化合物（例如，双功能小分子化合物），包含一种或多种异双功能化合物的组合物，以及使用这些异双功能化合物治疗患有某种疾病的受试者的方法。该披露还涉及用于识别此类异双功能化合物的方法。
• [EN] PROTEIN DEGRADING AGENT AND USE THEREOF IN TREATMENT OF DISEASES<br/>[FR] AGENT DE DÉGRADATION DE PROTÉINE ET SON UTILISATION DANS LE TRAITEMENT DE MALADIES<br/>[ZH] 蛋白降解剂及其在疾病治疗中的应用
  申请人：UNIV SHANGHAI TECH

  公开号：WO2021078301A1

  公开（公告）日：2021-04-29

  一种式(I)和式(II)的化合物或其盐、对映异构体、立体异构体、溶剂化物、多晶型物，及其用于治疗疾病的应用。 R 1-A 1-LIN-A 2-R 2 (I) R 12-A 12-LIN-A 22-R 22 (II)
• TROPOMYOSIN RECEPTOR KINASE (TRK) DEGRADATION COMPOUNDS AND METHODS OF USE
  申请人：Cullgen (Shanghai), Inc.

  公开号：US20210363146A1

  公开（公告）日：2021-11-25

  Bivalent compounds, compositions comprising one or more of the bivalent compounds, and methods of use the bivalent compounds for the treatment of certain disease in a subject in need thereof are provided. Methods for identifying such bivalent compounds are provided, either.
• 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.