2,3-Dihydro-2,4-dimethyl-1H-isoindole-1,3-dione | 83844-42-2

• 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: 2,3-Dihydro-2,4-dimethyl-1H-isoindole-1,3-dione
• 英文别名: 2,4-dimethyl-1H-isoindole-1,3(2H)-dione；3-amino-N-methylphthalimide；1,3-dimethylphthalimide；N,3-dimethylphthalimide；N,3-dimethylphtalimide；1H-Isoindole-1,3(2H)-dione, 2,4-dimethyl-；2,4-dimethylisoindole-1,3-dione
• CAS: 83844-42-2
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: XZEDZEXRESXLFF-UHFFFAOYSA-N

物化性质

• 熔点：
  136 °C
• 沸点：
  294.5±19.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-Dihydro-2,4-dimethyl-1H-isoindole-1,3-dione 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 以64%的产率得到4-Bromomethyl-2,3-dihydro-2-methyl-1H-isoindole-1,3-dione
  参考文献：
  名称：

  Identification of the Binding Modes of N-Phenylphthalimides Inhibiting Bacterial Thymidylate Synthase through X-Ray Crystallography Screening

  摘要：

  To identify specific bacterial thymidylate synthase (TS) inhibitors, we exploited phenolphthalein (PTH), which inhibits both bacterial and human enzymes. The X-ray crystal structure of Lactobacillus casei TS (LcTS) that binds PTH showed multiple binding modes of the inhibitor, which prevented a classical structure-based drug design approach. To overcome this issue, we synthesized two phthalimidic libraries that were tested against TS enzymes and then we performed X-ray crystallographic screening of the active compounds. Compounds 6A, 8A, and 12A showed 40-fold higher affinity for bacterial TS than human TS. The X-ray crystallographic screening characterized the binding mode of six inhibitors in complexes with LcTS. Of these, 20A, 23A, and 24A showed a common unique binding mode, whereas 8A showed a different, unique binding mode. A comparative analysis of the LcTS X-ray complexes that were obtained with the pathogenic TS enabled the selection of compounds 8A and 23A as specific compounds and starting points to be exploited for the specific inhibition of pathogen enzymes.

  DOI：

  10.1021/jm2005018
• 作为产物：
  描述：

  3-甲基四氢苯酐 在 溴 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 生成 2,3-Dihydro-2,4-dimethyl-1H-isoindole-1,3-dione
  参考文献：
  名称：

  Electron Impact Induced Loss of C-5/C-8 Substituents of 1,2,3,4-Tetrahydroisoquinolines, V: Synthesis and Mass Spectrometric Fragmentation of Dihydroisoindole Derivatives

  摘要：

  AbstractC‐8‐substituted N‐methyl‐1,2,3,4‐tetrahydroisoquinoline radical cations lose the complete substituent in a one step reaction giving rise to an unexpected ion at m/z 146, which is probably identical with the dihydroisoindolyl‐methyl‐cation A. The dihydroisoindoles 1, 10, and 16 were prepared as potentially alternative precursors of ion A. However, the ion at m/z 146 in their El mass spectra is of very low intensity, so CID‐experiments for structural comparison could not be performed. The electron impact induced fragmentations of 1, 10, and 16 are discussed.

  DOI：

  10.1002/ardp.19893220708

文献信息

• [EN] APOPTOSIS SIGNAL-REGULATING KINASE 1 (ASK 1) INHIBITOR COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS DE KINASE 1 (ASK 1) DE RÉGULATION DU SIGNAL DE L'APOPTOSE
  申请人：SIDECAR THERAPEUTICS INC

  公开号：WO2019070742A1

  公开（公告）日：2019-04-11

  Described herein are ASK1 inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders associated with ASK1 activity.

  本文描述了ASK1抑制剂，制备这类化合物的方法，包含这类化合物的药物组合物和药物，以及使用这类化合物治疗与ASK1活性相关的疾病、疾病或疾病的方法。
• Integrated Catalytic C−H Transformations for One-Pot Synthesis of 1-Arylisoindoles from Isoindolines via Palladium-Catalyzed Dehydrogenation Followed by C−H Arylation
  作者：Toshimichi Ohmura、Akihito Kijima、Michinori Suginome

  DOI：10.1021/ol2001232

  日期：2011.3.4

  A one-pot conversion of isoindolines to 1-arylisoindoles was established from palladium-catalyzed cascade C−H transformations, that is, the dehydrogenation of isoindolines to give isoindoles, with subsequent C−H arylation of the isoindoles.

  由钯催化的级联CH转换建立了异吲哚向一芳基异吲哚的一锅转化，也就是异吲哚的脱氢生成异吲哚，随后CH芳基化了异吲哚。
• 2-Methyltetrahydrofuran as a suitable green solvent for phthalimide functionalization promoted by supported KF
  作者：Vittorio Pace、Pilar Hoyos、María Fernández、José V. Sinisterra、Andrés R. Alcántara

  DOI：10.1039/c0gc00113a

  日期：——

  An efficient chemoselective nitrogen functionalization of phthalimides by using KF-Alumina in 2-methyltetrahydrofuran, a solvent obtained from renewal sources, is described.

  本文描述了一种高效的化学选择性氮功能化邻苯二甲酰亚胺的方法，使用KF-铝土矿在2-甲基四氢呋喃中进行，该溶剂来自可再生资源。
• 一种芳香取代茚酮类化合物的合成方法
  申请人：山东京博生物科技有限公司

  公开号：CN114369014A

  公开（公告）日：2022-04-19

  本发明涉及化学合成领域，具体提供了一种芳香取代茚酮类化合物的合成方法。首先取代邻苯二甲酸酐在有机溶剂中通甲胺气体发生氨解反应，在甲基迁移催化剂存在下通入氢气，发生甲基迁移和还原反应得到芳香取代茚酮类化合物。该合成方法具有反应条件温和、普适度高、原料易得、反应选择性高的优点。
• Quinoline derivatives as phosphodiesterase inhibitors
  申请人：Baldwin Robert Ian

  公开号：US20070142373A1

  公开（公告）日：2007-06-21

  There are provided according to the invention novel compounds of formula (I) or pharmaceutically acceptable salts thereof, wherein R 1 , R 2, R 19, R 20, and R 34 are as described in the specification, processes for preparing them, formulations containing them and their use in therapy for the treatment of inflammatory diseases.

  根据本发明提供了新型化合物(I)的公式或其药学上可接受的盐，其中R1、R2、R19、R20和R34如规范所述，制备它们的过程，含有它们的配方以及它们在治疗炎症性疾病中的用途。