2-(quinolin-6-yl)isoindolin-1,3-dione | 59679-81-1

• 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-(quinolin-6-yl)isoindolin-1,3-dione
• 英文别名: 6-quinolinylphthalimide；N-[6]quinolyl-phthalimide；N-[6]Chinolyl-phthalimid；N-6-Chinolylphthalimid；N-(6-Quinolinyl)phthalimide；2-quinolin-6-ylisoindole-1,3-dione
• CAS: 59679-81-1
• 化学式: C₁₇H₁₀N₂O₂
• 分子量: 274.279
• InChiKey: NHMZRXZDYXPWAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(quinolin-6-yl)isoindolin-1,3-dione 在 sodium cyanoborohydride 作用下， 以 溶剂黄146 为溶剂， 以81%的产率得到2-(1,2,3,4-tetrahydroquinolin-6-yl)isoindolin-1,3-dione
  参考文献：
  名称：

  Design, synthesis and inhibitory activity against Mycobacterium tuberculosis thymidine monophosphate kinase of acyclic nucleoside analogues with a distal imidazoquinolinone

  摘要：

  Thymidine monophosphate kinase from Mycobacterium tuberculosis (TMPKmt) has been proposed as an attractive target in the search of new agents to fight against tuberculosis. We recently reported that thymine derivatives carrying a naphtholactam or naphthosultam moiety at position 4 of a (Z)-butenyl chain inhibit TMPKmt in the sub mu M range. Here we describe the replacement of the planar naphtholactam and naphthosultam rings in our identified hits by 5,6-dihydro-1H-imidazo[4,5,1-ij]quinolinones and a 5,6-dihydro-1H,4H-1,2,5-thiadiazolo[4,3,2-ij]quinoline-2,2-dioxide where the planarity has been broken. Interestingly, these non-planar compounds were similarly potent against the target enzyme than their aromatic analogues, suggesting a bioisosteric behavior that may also be applied to other biologically active compounds. The synthesis of the different targeted imidazoquinolinones has been successfully performed via a hypervalent iodide mediated oxidative cyclization of N-methoxyureas catalized by bis(trifluoroacetoxy)iodobenzene (PIFA) expanding the reported use of this reagent for the synthesis of differently substituted imidazoquinolinones. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.056
• 作为产物：
  描述：

  6-氨基喹啉 、 苯酐 以 various solvent(s) 为溶剂， 生成 2-(quinolin-6-yl)isoindolin-1,3-dione
  参考文献：
  名称：

  N-喹啉基邻苯二甲酰亚胺异构体在电子碰撞电离中的断裂。

  摘要：

  异构的2-，3-，5-，6-和8-喹啉基邻苯二甲酰亚胺引起不同的电子碰撞电离质谱，这使得容易区分。就邻近效应和环状离子结构的稳定性而言，具体的裂解过程应合理化。碰撞诱导的解离光谱用于支持主要碎片离子的建议离子结构。

  DOI：

  10.1002/(sici)1096-9888(199606)31:6<676::aid-jms342>3.0.co;2-7

文献信息

• Fragmentation of IsomericN-Quinolinylphthalimides on Electron Impact Ionization
  作者：Adrian Weisz、Denis Andrzejewski、Asher Mandelbaum

  DOI：10.1002/(sici)1096-9888(199606)31:6<676::aid-jms342>3.0.co;2-7

  日期：1996.6

  The isomeric 2-, 3-, 5-, 6- and 8-quinolinylphthalimides give rise to different electron impact ionization mass spectra, which permit easy distinction. The specific fragmentation process are rationalized in terms of proximity effects and stabilization of cyclic ion structures. Collision-induced dissociation spectra were used to support the proposed ion structures of major fragment ions.

  异构的2-，3-，5-，6-和8-喹啉基邻苯二甲酰亚胺引起不同的电子碰撞电离质谱，这使得容易区分。就邻近效应和环状离子结构的稳定性而言，具体的裂解过程应合理化。碰撞诱导的解离光谱用于支持主要碎片离子的建议离子结构。
• DE590239
  申请人：——

  公开号：——

  公开（公告）日：——
• Design, synthesis and inhibitory activity against Mycobacterium tuberculosis thymidine monophosphate kinase of acyclic nucleoside analogues with a distal imidazoquinolinone
  作者：Olga Familiar、Hélène Munier-Lehmann、José Antonio Aínsa、María-José Camarasa、María-Jesús Pérez-Pérez

  DOI：10.1016/j.ejmech.2010.09.056

  日期：2010.12

  Thymidine monophosphate kinase from Mycobacterium tuberculosis (TMPKmt) has been proposed as an attractive target in the search of new agents to fight against tuberculosis. We recently reported that thymine derivatives carrying a naphtholactam or naphthosultam moiety at position 4 of a (Z)-butenyl chain inhibit TMPKmt in the sub mu M range. Here we describe the replacement of the planar naphtholactam and naphthosultam rings in our identified hits by 5,6-dihydro-1H-imidazo[4,5,1-ij]quinolinones and a 5,6-dihydro-1H,4H-1,2,5-thiadiazolo[4,3,2-ij]quinoline-2,2-dioxide where the planarity has been broken. Interestingly, these non-planar compounds were similarly potent against the target enzyme than their aromatic analogues, suggesting a bioisosteric behavior that may also be applied to other biologically active compounds. The synthesis of the different targeted imidazoquinolinones has been successfully performed via a hypervalent iodide mediated oxidative cyclization of N-methoxyureas catalized by bis(trifluoroacetoxy)iodobenzene (PIFA) expanding the reported use of this reagent for the synthesis of differently substituted imidazoquinolinones. (C) 2010 Elsevier Masson SAS. All rights reserved.