2-methyl-2H-isoindole-4,7-dione | 95832-83-0

• 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-methyl-2H-isoindole-4,7-dione
• 英文别名: 2-methylisoindole-4,7-dione
• CAS: 95832-83-0
• 化学式: C₉H₇NO₂
• 分子量: 161.16
• InChiKey: LLQVBRAPPFXECE-UHFFFAOYSA-N

物化性质

• 熔点：
  161-162 °C
• 沸点：
  320.8±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  39.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-2H-isoindole-4,7-dione 以 5,5-dimethyl-1,3-cyclohexadiene 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 9-methylisoindolo[4,5,6-ij][2,7]naphthyridin-7(9H)-one
  参考文献：
  名称：

  Scaffold hopping of sampangine: Discovery of potent antifungal lead compound against Aspergillus fumigatus and Cryptococcus neoformans

  摘要：

  Discovery of novel antifungal agents against Aspergillus fumigatus and Cryptococcus neoformans remains a significant challenge in current antifungal therapy. Herein the antifungal natural product sampangine was used as the lead compound for novel antifungal drug discovery. A series of D-ring scaffold hopping derivatives were designed and synthesized to improve antifungal activity and water solubility. Among them, the thiophene derivative S2 showed broad-spectrum antifungal activity, particularly for Aspergillus fumigatus and Cryptococcus neoformans. Moreover, compound S2 also revealed better water solubility than sampangine, which represents a promising antifungal lead compound for further structural optimization.

  DOI：

  10.1016/j.bmcl.2014.07.064
• 作为产物：
  描述：

  2-[甲基(三甲基甲硅烷基)氨基]乙腈 、 对苯醌 在 silver fluoride 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以64%的产率得到2-methyl-2H-isoindole-4,7-dione
  参考文献：
  名称：

  Synthetic application of cyanoaminosilanes as azomethine ylide equivalents

  摘要：

  DOI：

  10.1021/jo00221a010

文献信息

• 取代芳香四环类抗真菌化合物及其制备方法与 应用
  申请人：中国人民解放军第二军医大学

  公开号：CN103254191B

  公开（公告）日：2016-01-27

  本发明涉及医药技术领域。本发明提供了一种取代芳香四环类化合物及其药学上可接受的盐，所述的取代芳香四环类化合物，其结构通式如下：，本发明还提供上述化合物的制备方法，以及在制备抗真菌药物中的应用。
• Synthesis and biological evaluation of novel heterocyclic quinones as inhibitors of the dual specificity protein phosphatase CDC25C
  作者：Olivier Lavergne、Anne-Cécile Fernandes、Laetitia Bréhu、Alban Sidhu、Marie-Christine Brézak、Grégoire Prévost、Bernard Ducommun、Marie-Odile Contour-Galcera

  DOI：10.1016/j.bmcl.2005.09.030

  日期：2006.1

  A focused set of heterocyclic quinones based on the benzothiazole, benzoxazole, benzimidazole, indazole and isoindole was prepared and screened with respect to the inhibition of the phosphatase activity of CDC25C. Benzoxazole- and benzothiazole-diones were at least 50 times more potent in inhibiting CDC25C than their benzimidazole-indazole- or isoindole-dione counterparts. These in vitro activities

  制备了一组基于苯并噻唑，苯并恶唑，苯并咪唑，吲唑和异吲哚的杂环醌，并就抑制CDC25C的磷酸酶活性进行了筛选。苯并恶唑和苯并噻唑二酮在抑制CDC25C方面的功效至少是苯并咪唑-吲唑-或异吲哚-二酮类似物的50倍以上。这些体外活性与用Mia PaCa-2和DU-145人肿瘤细胞培养物观察到的抗增殖作用高度相关。通过WST-1比色测定获得的IC（50）值范围对于苯并恶唑或苯并噻唑二酮为0.10至0.50 microM，而对于其他杂环二酮则为10 microM以上。
• 2H-Isoindol-4,7-dione durch Addition von Azomethinyliden an 1,4-Benzochinone
  作者：Manfred Schubert-Zsilavecz、Werner Likussar、Dagmar Gusterhuber、Astrid Michelitsch

  DOI：10.1007/bf00809659

  日期：1991.5

  A new approach to the synthesis of 2H-isoindole-4,7-diones is described. Heating alpha-amino acids with carbonyl compounds generates azomethine ylides through the elimination of water and carbon dioxide. The ylides were captured by quinones forming 2H-isoindole-4,7-diones, 2,3,3a,7a-tetrahydro-1H-isoindole-4,7-diones and 2,3-dihydro-1H-pyrrolo[2,1-a]isoindole-6,9-diones. The structures were established on the basis of spectroscopy (NMR, mass).
• Synthese und polarographisches Verhalten von 2H-Isoindol-4,7-dionen
  作者：W. Likussar、A. Michelitsch、M. Schubert-Zsilavecz、D. Gusterhuber

  DOI：10.1007/bf00823429

  日期：1991.11

  2-Phenylthio-1,4-benzoquinone (1 a) reacts with azomethine ylide AY-A to give 2-methyl-5-phenylthio-2H-isoindole-4,7-dione (4 f). With 2-(N-methylanilino)-5-methyl-1,4-benzoquinone (1 b), the azomethine ylide AY-B undergoes cycloaddition to yield an inseparable mixture of 5a-methyl-8-(N-methylanilino)-2,3,5,5a,9a,9b-hexahydro-pyrrolo[2,1-a]1H-isoindole-6,9-dione (5 bI) and 9a-methyl-7-(N-methylanilino)-2,3,5,5a,9a,9b-hexahydropyrrolo[2,1-a]1H-isoindole-6,9-dione (5 bII). The structures of 5 bI and 5 bII were established on basis of two-dimensional-NMR-techniques. The mechanism of the cycloaddition of azomethine ylides to 1,4-quinones was studied on basis of cyclovoltammetric investigations. To determine the electron affinity of the isoindoledione derivatives 4 a-f and 5 a-b the peak potentials were measured by differential pulse polarography (DPP).
• Cycloadditions of non-stabilized azomethine ylides and quinones synthesis of the isoindole
  作者：Kathlyn A. Parker、Isaac D. Cohen、Albert Padwa、William Dent

  DOI：10.1016/s0040-4039(01)91258-4

  日期：1984.1