2-benzyl-5-hydroxyisoindoline-1,3-dione | 3997-85-1

• 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-benzyl-5-hydroxyisoindoline-1,3-dione
• 英文别名: 2-benzyl-5-hydroxy-isoindole-1,3-dione；2-Benzyl-5-hydroxyisoindole-1,3-dione
• CAS: 3997-85-1
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: ZJCVGFCOHPVDMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzyl-5-hydroxyisoindoline-1,3-dione 在 bis-triphenylphosphine-palladium(II) chloride 盐酸 、 溶剂黄146 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (E)-3-(2-Benzyl-1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl)-acrylic acid
  参考文献：
  名称：

  设计，合成和评估带有环酰胺/酰亚胺的异羟肟酸衍生物作为类选择性组蛋白脱乙酰基酶（HDAC）抑制剂。

  摘要：

  在我们根据沙利度胺进行的结构开发研究中制备的一系列带有环状酰胺/酰亚胺基团作为连接基和/或帽结构的异羟肟酸衍生物显示出对类组有效的组蛋白脱乙酰基酶（HDAC）的抑制活性。结构-活性关系研究表明，在环状酰胺/酰亚胺氮原子上引入的取代基的空间特征，酰胺/酰亚胺羰基的存在，异羟肟酸的结构，连接基团的形状以及它们之间的距离结合锌的异羟肟酸基团和帽结构对于抑制HDAC的活性和类别选择性都很重要。具有代表性的化合物（30w）显示出强效的p21启动子活性，与曲古抑菌素A（TSA）相当，

  DOI：

  10.1016/j.bmc.2006.07.008
• 作为产物：
  描述：

  4-羟基邻苯二甲酸 生成 2-benzyl-5-hydroxyisoindoline-1,3-dione
  参考文献：
  名称：

  Design and synthesis of phthalimide-type histone deacetylase inhibitors

  摘要：

  Several hydroxamic acid derivatives with a substituted phthalimicle group as a linker and/or cap structure, prepared during structural development studies based on thalidomide, were found to have historic deacetylase (HDAC)-inhibitory activity. Structure-activity relationship studies indicated that nature of the substituent introduced at the phthalimide nitrogen atom, introduction of a hydroxamic acid structure, and distance between the N-hydroxyl group and the cap structure are important for HDAC-inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.048

文献信息

• Efficient conversion of acids and esters to amides and transamidation of primary amides using OSU-6
  作者：Baskar Nammalwar、Nagendra Prasad Muddala、Field M. Watts、Richard A. Bunce

  DOI：10.1016/j.tet.2015.10.016

  日期：2015.12

  with strong Bronsted acid properties, has been used to promote the high-yield conversion of carboxylic acids and esters to carboxamides as well as transamidations of primary amides in a one-pot solventless approach. A metal-free heterogeneous catalyst that promotes all of these processes has not been previously reported. OSU-6 enables these transformations to proceed in shorter times and at lower temperatures

  OSU-6，具有强布朗斯台德酸性质的MCM-41型六角孔二氧化硅，已被用来促进的羧酸和酯的高产转化为羧酰胺，以及在单罐无溶剂方法伯酰胺的transamidations。先前尚未报道可促进所有这些过程的无金属非均相催化剂。OSU-6使这些转化能够在更短的时间和更低的温度下针对多种基材进行。一个附加的好处是，该催化剂可以回收和不活动的显著损失重复使用多次。
• WO2008/20306
  申请人：——

  公开号：——

  公开（公告）日：——
• Diphenyl ether herbicides
  申请人：SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.

  公开号：EP0145078B1

  公开（公告）日：1988-10-12
• [EN] ISOINDOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'ISOINDOLE
  申请人：PFIZER PROD INC

  公开号：WO2008020306A2

  公开（公告）日：2008-02-21

  [EN] This invention relates to compounds of formula (I) or pharmaceutically acceptable salts thereof, a process of making these compounds, pharmaceutical compositions containing one or more of these compounds or their salts, and their use for the treatment of schizophrenia, bipolar disorder, or other central nervous system disorders.
  [FR] La présente invention concerne des composés de formule (I) ou leurs sels pharmaceutiquement acceptables, un procédé de fabrication de ces composés, des compositions pharmaceutiques contenant un ou plusieurs de ces composés ou leurs sels et leur utilisation pour le traitement de la schizophrénie, du trouble bipolaire ou d'autres affections du système nerveux central.
• Design and synthesis of phthalimide-type histone deacetylase inhibitors
  作者：Chihiro Shinji、Takanori Nakamura、Satoko Maeda、Minoru Yoshida、Yuichi Hashimoto、Hiroyuki Miyachi

  DOI：10.1016/j.bmcl.2005.07.048

  日期：2005.10

  Several hydroxamic acid derivatives with a substituted phthalimicle group as a linker and/or cap structure, prepared during structural development studies based on thalidomide, were found to have historic deacetylase (HDAC)-inhibitory activity. Structure-activity relationship studies indicated that nature of the substituent introduced at the phthalimide nitrogen atom, introduction of a hydroxamic acid structure, and distance between the N-hydroxyl group and the cap structure are important for HDAC-inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.