5-羟基-2-苯基异吲哚-1,3-二酮 | 3975-50-6

• 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
• 中文名称: 5-羟基-2-苯基异吲哚-1,3-二酮
• 英文名称: 5-hydroxy-2-phenylisoindoline-1,3-dione
• 英文别名: 5-hydroxy-2-phenyl-isoindoline-1,3-dione；5-Hydroxy-2-phenyl-isoindolin-1,3-dion；5-hydroxy-2-phenylisoindole-1,3-dione
• CAS: 3975-50-6
• 化学式: C₁₄H₉NO₃
• 分子量: 239.23
• InChiKey: HCUAWJNHCZEMJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  5-羟基-2-苯基异吲哚-1,3-二酮 在 水 、 potassium carbonate 、 溶剂黄146 、 lithium hydroxide 、 锌 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 0.08h， 生成 4-chloro-3'-((1-oxo-2-phenylisoindolin-5-yloxy)methyl)biphenyl-3-carboxylic acid
  参考文献：
  名称：

  Design and Synthesis of an Orally Active Metabotropic Glutamate Receptor Subtype-2 (mGluR2) Positive Allosteric Modulator (PAM) That Decreases Cocaine Self-Administration in Rats

  摘要：

  The modification of 3'((2-cyclopentyl-6,7-dimethyl-1-oxo-2,3-dihydro-1 H-inden-5-yloxy)methyl)biphenyl 4-carboxylic acid (BINA, 1) by incorporating heteroatoms into the structure and replacing the cyclopentyl moiety led to the development of new mGluR2 positive allosteric modulators (PAMs) with optimized potency and superior druglike properties These analogues are more potent than 1 in vitro and are highly selective for mGluR2 vs other mGluR subtypes They have significantly improved pharmacokinetic (PK) properties, with excellent oral bioavailability and brain penetration The benzisothiazol-3-one derivative 14 decreased cocaine self-administration in rats, providing proof-of-concept for the use of mGluR2 PAMs for the treatment of cocaine dependence

  DOI：

  10.1021/jm1012165
• 作为产物：
  描述：

  4-羟基邻苯二甲酸 生成 5-羟基-2-苯基异吲哚-1,3-二酮
  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

• Design, synthesis, and evaluation of cyclic amide/imide-bearing hydroxamic acid derivatives as class-selective histone deacetylase (HDAC) inhibitors
  作者：Chihiro Shinji、Satoko Maeda、Keisuke Imai、Minoru Yoshida、Yuichi Hashimoto、Hiroyuki Miyachi

  DOI：10.1016/j.bmc.2006.07.008

  日期：2006.11

  A series of hydroxamic acid derivatives bearing a cyclic amide/imide group as a linker and/or cap structure, prepared during our structural development studies based on thalidomide, showed class-selective potent histone deacetylase (HDAC)-inhibitory activity. Structure-activity relationship studies indicated that the steric character of the substituent introduced at the cyclic amide/imide nitrogen

  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，
• Synthesis and reactivity of a novel group of hydroxylamine-containing 2π- and 4π-components
  作者：Alan J. Pearce、Daryl S. Walter、Christopher S. Frampton、Timothy Gallagher

  DOI：10.1039/a708380g

  日期：——

  The synthesis of hydroxylamine-based reagents, alkene 2, alkyne 3 and a butadienyl variant pyrone 4 are described. While the relative instability of alkyne 3 has limited further evaluation, alkene 2 and pyrone 4 successfully participate in 1,3-dipolar and Diels–Alder cycloaddition reactions respectively. Reaction of 4 with DMAD gives O-arylated hydroxylamine 13, the structure of which is confirmed by crystallographic analysis.

  本文介绍了羟胺基试剂、烯烃 2、炔烃 3 和丁二烯变体吡喃酮 4 的合成过程。虽然炔 3 的相对不稳定性限制了进一步的评估，但烯 2 和吡喃酮 4 分别成功地参与了 1,3-二极和 DielsâAlder 环加成反应。4 与 DMAD 反应生成 O-芳基化的羟胺 13，其结构已通过晶体分析得到证实。
• Aryl triflate compound, radiologically acid producing agent,
  申请人：Hitachi Chemical Company Ltd.

  公开号：US05198402A1

  公开（公告）日：1993-03-30

  Aryl triflate compounds can generate a strong acid when exposed to irradiation of radiation and can be used as an acid generator in a radiologically-acid-producing agent system and a radiosensitive composition.

  苯基三氟甲烷磺酸酯化合物在辐射照射下可以产生强酸，并可用作放射性产酸剂系统和放射敏感组合物中的酸发生剂。
• Aryl triflate compounds and radiologically acid producing agents thereof
  申请人：Hitachi Chemical Co., Ltd.

  公开号：US05302725A1

  公开（公告）日：1994-04-12

  Aryl triflate compounds can generate a strong acid when exposed to irradiation of radiation and can be used as an acid generator in a radiologically-acid-producing agent system and a radiosensitive composition.

  芳基三氟甲烷基化合物在辐射照射下可以产生强酸，并可用作放射性酸生成剂系统和放射敏感组合物中的酸发生剂。
• Aryl triflate compound, radiologically acid producing agent, radiologically acid producing agent system, and radiosensitive composition
  申请人：HITACHI CHEMICAL CO., LTD.

  公开号：EP0537879A1

  公开（公告）日：1993-04-21

  Aryl triflate compounds can generate a strong acid when exposed to irradiation of radiation and can be used as an acid generator in a radiologically-acid-producing agent system and a radiosensitive composition.

  三酸芳基酯化合物在受到辐射辐照时可生成强酸，可用作辐射产酸剂系统和辐射敏感组合物中的产酸剂。