ethyl 2-benzyl-3-methyl-4-oxo-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate | 1148040-85-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-benzyl-3-methyl-4-oxo-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate
• CAS: 1148040-85-0
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: UQVMBIHRFFSNQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  48.3
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-benzyl-3-methyl-4-oxo-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate 以 乙醇 、 甲苯 为溶剂， 反应 30.0h， 生成 ethyl 8-benzyl-9-methyl-3-(phenylsulfonyl)-1,5,6,8-tetrahydro-2H-pyrrolo[3,4-h]quinoline-2-one-7-carboxylate
  参考文献：
  名称：

  吡咯并[3,4- h ]喹啉酮类新型光化学治疗剂

  摘要：

  合成吡咯并[3,4- h ]喹啉-2-酮作为角呋喃香豆素当归的氮等价物，目的是获得具有增加的抗增殖活性和较低的不良毒性作用的新型光化学治疗剂。寻求一种通用的合成途径以分离具有在吡咯部分上的良好取代模式的新环系统的衍生物。新化合物的光生物学筛选显示出强大的光毒性作用和很大的UVA剂量依赖性，在亚微摩尔水平下达到IC 50值。诱导的细胞光细胞毒性与线粒体和溶酶体的参与，细胞周期谱的改变和膜脂质过氧化的凋亡有关。

  DOI：

  10.1016/j.bmc.2011.02.023
• 作为产物：
  描述：

  3-甲基-4-氧代-4,5,6,7-四氢-2H-异吲哚-1-甲酸乙酯 、 氯化苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以94%的产率得到ethyl 2-benzyl-3-methyl-4-oxo-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate
  参考文献：
  名称：

  Pyrano [2,3- e ] isoindol-2-ones，new angelicin heteroanalogues

  摘要：

  据报道，吡喃并[2,3 - e ] isoindol-2-one环系统，即当归的杂类似物，可以方便地合成。我们的合成方法包括使用5-二烷基氨基-或5-羟基亚甲基中间体作为结构单元，使吡喃环在异吲哚部分上的成环反应。研究了新衍生物的光抗增殖活性。其中一些在8位带有苄基的化合物在微摩尔范围内具有IC 50活性。细胞的细胞毒性涉及细胞凋亡，细胞周期概况的改变和膜的光损伤。

  DOI：

  10.1016/j.bmcl.2009.01.096

文献信息

• Synthesis of the new ring system 6,8-dihydro-5H-pyrrolo[3,4-h]quinazoline
  作者：Paola Barraja、Virginia Spanò、Patrizia Diana、Anna Carbone、Girolamo Cirrincione

  DOI：10.1016/j.tetlet.2009.07.045

  日期：2009.9

  A convenient synthesis of the pyrrolo[3,4-h]quinazoline ring system is reported. Our synthetic approach consisted of the annelation of a pyrimidine ring to an isoindole moiety using tetrahydroisoindole-4-ones as building blocks. The antiproliferative activity of the new compounds was investigated and one of them showed antitumor activity against all the 59 tested cell lines at micromolar concentrations

  报道了吡咯并[3，4- h ]喹唑啉环系统的方便合成。我们的合成方法包括使用四氢异吲哚-4-酮作为构建基，使嘧啶环与异吲哚部分成环。研究了新化合物的抗增殖活性，其中一种在微摩尔浓度（1.46-18.4μM）下显示了对所有59种测试细胞系的抗肿瘤活性。
• Convenient synthesis of pyrrolo[3,4-g]indazole
  作者：Virginia Spanò、Alessandra Montalbano、Anna Carbone、Barbara Parrino、Patrizia Diana、Girolamo Cirrincione、Paola Barraja

  DOI：10.1016/j.tet.2013.09.003

  日期：2013.11

  The synthesis of a novel class of tetrahydropyrrolo[3,4-g]indazoles is reported, by annelation of the pyrazole ring on the isoindole moiety by means of 5-hydroxymethylene tetrahydroisoindole-4-ones key intermediates, with good regioselectivity. Dihydroderivatives were also obtained by oxidation with DDQ of the corresponding tetrahydropyrrolo[3,4-g]indazoles. The growth inhibitory effect was evaluated at the National Cancer Institute of Bethesda and some derivatives showed modest activity. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of a new class of pyrrolo[3,4-h]quinazolines with antimitotic activity
  作者：Virginia Spanò、Alessandra Montalbano、Anna Carbone、Barbara Parrino、Patrizia Diana、Girolamo Cirrincione、Ignazio Castagliuolo、Paola Brun、Olaf-Georg Issinger、Silvia Tisi、Irina Primac、Daniela Vedaldi、Alessia Salvador、Paola Barraja

  DOI：10.1016/j.ejmech.2013.10.014

  日期：2014.3

  A new series of pyrrolo[3,4-h]quinazolines was conveniently prepared with a broad substitution pattern. A large number of derivatives was obtained and the cellular cytotoxicity was evaluated in vitro against 5 different human tumor cell lines with GI(50) values reaching the low micromolar level (1.3-19.8 mu M). These compounds were able to induce cell death mainly by apoptosis through a mitochondrial dependent pathway. Selected compounds showed antimitotic activity and a reduction of tubulin polymerization in a concentration-dependent manner. Moreover, they showed anti-angiogenic properties since reduced in vitro endothelial cell migration and disrupted HUVEC capillary-like tube network in Matrigel. (C) 2013 Elsevier Masson SAS. All rights reserved.