5,11-dihydrobenzo[4,5]imidazo[1,2-b]isoquinolin-11-one | 26203-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 5,11-dihydrobenzo[4,5]imidazo[1,2-b]isoquinolin-11-one
• 英文别名: 5,11-dihydrobenzimidazo[1,2-b]isoquinoline-11-one；benzo[4,5]imidazo[1,2-b]isoquinolin-11(5H)-one；benzimidazo[1,2-b]isoquinolin-11(5H)-one；5H-benzo[4,5]imidazo[1,2-b]isoquinolin-11-one；5H-benzimidazolo[1,2-b]isoquinolin-11-one
• CAS: 26203-76-9
• 化学式: C₁₅H₁₀N₂O
• mdl: MFCD03408327
• 分子量: 234.257
• InChiKey: QHFYYHVXZTVQPY-UHFFFAOYSA-N

物化性质

• 熔点：
  324-326 °C
• 沸点：
  448.3±45.0 °C(predicted)
• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,11-dihydrobenzo[4,5]imidazo[1,2-b]isoquinolin-11-one 在 氢溴酸 、 溶剂黄146 作用下， 以 溶剂黄146 为溶剂， 反应 44.0h， 生成 spiro[benzimidazo[1,2-b]isoquinolin-6(11H),2'-indan]-1',11-dione
  参考文献：
  名称：

  缩合异喹啉。17.苯并咪唑[1,2-b]异喹啉-11（5H）-one在烷基化反应中的烯胺性质

  摘要：

  DOI：

  10.1023/b:cohc.0000046697.89737.65
• 作为产物：
  描述：

  高邻苯二甲酸酐 、 邻苯二胺 在 溶剂黄146 作用下， 反应 4.0h， 以90%的产率得到5,11-dihydrobenzo[4,5]imidazo[1,2-b]isoquinolin-11-one
  参考文献：
  名称：

  Ling, Ke-Qing; Chen, Xian-Yang; Fun, Hoong-Kun, Journal of the Chemical Society. Perkin transactions I, 1998, # 24, p. 4147 - 4157

  摘要：

  DOI：

文献信息

• Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes
  作者：Qiao Chen、Tingshun Zhu、Pankaj Kumar Majhi、Chengli Mou、Huifang Chai、Jingjie Zhang、Shitian Zhuo、Yonggui Robin Chi

  DOI：10.1039/c8sc03480j

  日期：——

  An N-heterocyclic carbene-catalyzed direct oxidative coupling of enals and di(hetero)arylmethanes allows for quick access to optical pure benzimidazole-fused lactams.

  通过N-杂环卡宾催化的炔醛和二(杂)芳基甲烷的直接氧化偶联，可以快速获得光学纯的苯并咪唑-融合内酰胺。

• Singlet oxygen reactions of benzannelated isoquinolinones
  作者：Ke-Qing Ling、Hu Cai、Jia-Hai Ye、Jian-Hua Xu

  DOI：10.1016/s0040-4020(98)01186-7

  日期：1999.2

  Tetraphenylporphin (TPP) or methylene blue (MB) sensitized photooxygenation reactions of benzannelated isoquinolinones 3 and 4 took place by initial attack of singlet oxygen on the enol ether-enamine CC double bond and proceeded via zwitterionic (10, 29) and endoperoxidic (11, 28, 30) intermediates. The product for 3 was 5 exclusively in MeCN, and 5 and the solvent trapping products 6 in MeOH. For 4, the products

  四苯基卟吩（TPP）或亚甲基蓝（MB）benzannelated异喹啉酮类的光氧化致敏反应3和4发生由在烯醇醚-烯胺CC双键的单线态氧的初始攻击，并着手通过两性离子（10，29）和endoperoxidic（11，28，30）中间体。为产品3是5只在MeCN，和5和溶剂捕集产品6的MeOH。对于4，在MeCN中的产物为25（和26），而在MeOH中，还获得了溶剂捕集的产物314b。还观察到两性离子中间体在4d形成32的单线态氧反应过程中的分子内捕集。
• Flower-shaped ZnO nanoparticles as an efficient, heterogeneous and reusable catalyst in the synthesis of N-arylhomophthalimides and benzannelated isoquinolinones
  作者：Varadhan Krishnakumar、Kesarla Mohan Kumar、Badal Kumar Mandal、Fazlur-Rahman Nawaz Khan

  DOI：10.1007/s11164-012-0511-3

  日期：2012.10

  A simple and green protocol, developed utilizing an efficient, heterogeneous and recyclable catalyst, i.e. zinc oxide nanoparticles (ZnO NPs)-mediated synthesis of N-arylhomophthalimides and benzannelated isoquinolinones, is reported. The structures of the desired products were characterized by FTIR, 1H NMR, 13C NMR, and HRMS techniques. The ZnO NPs exhibited excellent catalytic activity and the proposed methodology is capable of providing the desired products in good yield and purity.

  报道了一种简单且绿色的合成方法，该方法利用一种高效、异质且可回收的催化剂，即氧化锌纳米颗粒（ZnO NPs），进行N-芳基同苯二甲酰亚胺和苯并取代的异喹啉酮的合成。所需产品的结构通过傅里叶变换红外光谱（FTIR）、1H核磁共振（NMR）、13C核磁共振（NMR）和高分辨率质谱（HRMS）技术进行表征。ZnO NPs表现出优异的催化活性，所提出的方法能够以良好的产率和纯度提供所需产品。
• New potent imidazoisoquinolinone derivatives as anti-Trypanosoma cruzi agents: Biological evaluation and structure–activity relationships
  作者：Mariela Bollini、Juan José Casal、Diego E. Alvarez、Lucía Boiani、Mercedes González、Hugo Cerecetto、Ana María Bruno

  DOI：10.1016/j.bmc.2009.01.011

  日期：2009.2

  A series of novel benzoimidazo andN-aryl-5-oxo-imidazo[1,2-b] isoquinoline-10-carbothioamides was developed. All the compounds were evaluated for their in vitro action against the epimastigote form of Trypanosoma cruzi. Four of them showed higher activity than Nifurtimox. Their unspecific cytotoxicity was evaluated using HeLa and L6 cells, being non-toxic at concentrations at least 15 and 200 times higher than that of T. cruzi IC50. To gain insight into the mechanism of action, their DNA binding properties and reactivity with glutathione were studied, and QSAR study was performed. (c) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of 3-aminoisoquinolin-1(2H)-one based inhibitors of the dual-specificity phosphatase Cdc25B
  作者：Kara M. George Rosenker、William D. Paquette、Paul A. Johnston、Elizabeth R. Sharlow、Andreas Vogt、Ahmet Bakan、John S. Lazo、Peter Wipf

  DOI：10.1016/j.bmc.2015.01.043

  日期：2015.6

  The cell division cycle 25B dual specificity phosphatase (Cdc25B) regulates the normal progression of the mammalian cell cycle by dephosphorylating and activating cyclin-dependent kinase (Cdk) complexes, particularly in response to DNA damage. Elevated Cdc25B levels enable a bypass of normal cell cycle checkpoints, and the overexpression of Cdc25B has been linked to a variety of human cancers. Thus, Cdc25B is an attractive target for the development of anticancer therapeutics. Herein we describe the synthesis and biological evaluation of a series of non-quinoid inhibitors of Cdc25B containing the 3-aminoisoquinolin-1(2H)-one pharmacophore. In addition to several strategies that address specific substitution patterns on isoquinolines, we have applied a regioselective Pd-catalyzed cross-coupling methodology to synthesize a new lead structure, 6-(3-aminophenyl)-3-(phenylamino) isoquinolin-1(2H)-one (13), which proved to be a reversible, competitive Cdc25B inhibitor with a K-i of 1.9 mu M. Compound 13 prevented human cancer cell growth and blocked Cdc25B-mediated mitotic checkpoint bypass. Molecular docking studies support binding near the catalytic site. (C) 2015 Published by Elsevier Ltd.