pyrazino[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one | 952062-63-4

• 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: pyrazino[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one
• 英文别名: pyrazino[2',1':2,3]imidazo[4,5-c]isoquinolin-5(6H)-one；6H-pyrimido[4',3':1,2]imidazo[5,4-c]isoquinolin-5-one；6H-Pyrimido[4'',3'':1,2]imidazo[5,4-c]isoquinolin-5-one；9,11,14,17-tetrazatetracyclo[8.7.0.02,7.011,16]heptadeca-1(10),2,4,6,12,14,16-heptaen-8-one
• CAS: 952062-63-4
• 化学式: C₁₃H₈N₄O
• 分子量: 236.233
• InChiKey: DYAZPVTUJDWMKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 tetrafluorohydroboric acid 作用下， 以 水 、 正丁醇 为溶剂， 反应 0.33h， 生成 pyrazino[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one
  参考文献：
  名称：

  Towards molecular diversity: dealkylation of tert-butyl amine in Ugi-type multicomponent reaction product establishes tert-butyl isocyanide as a useful convertible isonitrile

  摘要：

  随着一种新型微波辅助单锅联产去叔丁基化的开发，在Ugi型多组分反应生成物中，叔丁基异氰酸酯作为一种有用的可转化异腈首次被探讨，从而获得了制药上重要的多环氮融合咪唑杂环的分子多样性。

  DOI：

  10.1039/c0ob00022a

文献信息

• A chemoselective Ugi-type reaction in water using TMSCN as a functional isonitrile equivalent: generation of heteroaromatic molecular diversity
  作者：Sankar Kumar Guchhait、Vikas Chaudhary、Chetna Madaan

  DOI：10.1039/c2ob26733k

  日期：——

  KF-mediated nucleophilic activation of TMSCN as a functional isonitrile equivalent establishes an efficient and chemoselective Ugi-type multicomponent reaction of a heterocyclic amidine and aldehyde with TMSCN in water. In this approach, the use of isocyanide is circumvented, known competing reactions are virtually eliminated, pure products are obtained by a non-chromatographic method, and therapeutically relevant and diverse N-fused 3-aminoimidazoles can be prepared from a wide variety of aldehydes and heterocyclic amidines. This reaction coupling with cascade cyclization provides various privileged tetracyclic heteroaromatic scaffolds.

  KF催化的TMSCN亲核活化作为功能性异腈等价物，建立了羟基胺和醛与TMSCN在水中进行的高效且化学选择性的Ugi类型多组分反应。在这种方法中，避免了异氰酸酯的使用，已知的竞争反应几乎被消除，纯产品通过非色谱法获得，并且可从多种醛和杂环胺制备出具有治疗相关性和多样性的N-融合3-氨基咪唑。该反应结合级联环化提供了多种特权的四环杂芳烃骨架。
• Synthesis of isoquinolinone-based tetracycles as poly (ADP-ribose) polymerase-1 (PARP-1) inhibitors
  作者：Hee-Kyung Rhee、So Yun Lim、Mi-Ja Jung、Youngjoo Kwon、Myung-Hwa Kim、Hea-Young Park Choo

  DOI：10.1016/j.bmc.2009.09.014

  日期：2009.11

  The isoquinolinone-based tetracyclic compounds were designed and synthesized and their PARP-1 inhibitory activity was evaluated. Most of synthesized compounds showed fairly good activity. Also the most active compound 6 showed its activity on potentiation of anticancer agents, temozolamide and etoposide, by 1.7 times, respectively.

  设计并合成了基于异喹啉酮的四环化合物，并评估了其对PARP-1的抑制活性。大多数合成的化合物显示出相当好的活性。活性最高的化合物6也显示出其对抗癌药替莫唑胺和依托泊苷的增强作用，分别是其1.7倍。