2,2'-[1,4-丁烷二基二(氧基)]二-1H-异吲哚-1,3(2H)-二酮 | 94464-30-9

• 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
• 中文名称: 2,2'-[1,4-丁烷二基二(氧基)]二-1H-异吲哚-1,3(2H)-二酮
• 英文名称: 1,4-Bis-phthalimido-oxy-butan
• 英文别名: N,N'-butane-1,4-diyldioxy-bis-phthalimide；2-(4-((1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy)butoxy)-1H-isoindole-1,3(2H)-dione；2-[4-(1,3-dioxoisoindol-2-yl)oxybutoxy]isoindole-1,3-dione
• CAS: 94464-30-9
• 化学式: C₂₀H₁₆N₂O₆
• 分子量: 380.357
• InChiKey: PHIWXXXLKDTQLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  93.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2'-[1,4-丁烷二基二(氧基)]二-1H-异吲哚-1,3(2H)-二酮 以 乙醇 、 水 为溶剂， 生成 1,4-二(氨基氧基)丁烷
  参考文献：
  名称：

  Synthesis and Structural Characterization of Bromo-Substituted Salamo-Type Bisoximes Based on Bis(aminooxy)alkane and 3,5-Dibromosalicylaldehyde

  摘要：

  通过3,5-二溴水杨醛与1,2-双(氨基氧基)乙烷、1,3-双(氨基氧基)丙烷和1,4-缩合反应合成了一系列溴代Salamo型双肟H2L1-H2L3。分别在乙醇介质中制备双（氨基氧基）丁烷，并通过元素分析、IR 和 1H NMR 光谱进行表征。 Salamo型双肟H2L1的晶体结构中，由分子内氢键、p…p堆积相互作用和分子间Br…Br卤键形成无限一维超分子双链结构。

  DOI：

  10.14233/ajchem.2015.17470
• 作为产物：
  描述：

  1,4-二溴丁烷 、 N-羟基邻苯二甲酰亚胺 在 三乙胺 作用下， 反应 75.0h， 生成 2,2'-[1,4-丁烷二基二(氧基)]二-1H-异吲哚-1,3(2H)-二酮
  参考文献：
  名称：

  Synthesis and Structural Characterization of Bromo-Substituted Salamo-Type Bisoximes Based on Bis(aminooxy)alkane and 3,5-Dibromosalicylaldehyde

  摘要：

  通过3,5-二溴水杨醛与1,2-双(氨基氧基)乙烷、1,3-双(氨基氧基)丙烷和1,4-缩合反应合成了一系列溴代Salamo型双肟H2L1-H2L3。分别在乙醇介质中制备双（氨基氧基）丁烷，并通过元素分析、IR 和 1H NMR 光谱进行表征。 Salamo型双肟H2L1的晶体结构中，由分子内氢键、p…p堆积相互作用和分子间Br…Br卤键形成无限一维超分子双链结构。

  DOI：

  10.14233/ajchem.2015.17470

文献信息

• Synthesis and Structural Characterization of Bromo-Substituted Salamo-Type Bisoximes Based on Bis(aminooxy)alkane and 3,5-Dibromosalicylaldehyde
  作者：G.-X. An、Y. Zhang、L. Wang、Y.-X. Sun、X.-Y. Dong、W.-K. Dong

  DOI：10.14233/ajchem.2015.17470

  日期：——

  A series of bromo-substituted Salamo-type bisoximes H2L1-H2L3 have been synthesized through condensation reactions of 3,5-dibromosalicylaldehyde with 1,2-bis(aminooxy)ethane, 1,3-bis(aminooxy)propane and 1,4-bis(aminooxy)butane in ethanol medium, respectively and characterized by elemental analyses, IR and 1H NMR spectra. In the crystal structure of Salamo-type bisoximes H2L1, an infinite 1D supramolecular double chain-like structure is formed by intramolecular hydrogen bonds, p···p stacking interactions and intermolecular Br···Br halogen bondings.

  通过3,5-二溴水杨醛与1,2-双(氨基氧基)乙烷、1,3-双(氨基氧基)丙烷和1,4-缩合反应合成了一系列溴代Salamo型双肟H2L1-H2L3。分别在乙醇介质中制备双（氨基氧基）丁烷，并通过元素分析、IR 和 1H NMR 光谱进行表征。 Salamo型双肟H2L1的晶体结构中，由分子内氢键、p…p堆积相互作用和分子间Br…Br卤键形成无限一维超分子双链结构。
• Synthesis and Characterization of Methoxy-Substituted Salamo-Type Bisoximes Based on Bis(aminooxy)alkane and 3-Methoxy-2-hydroxybenzaldehyde
  作者：Zong-Li Ren、Su-Xia Gao、Yang Zhang、Li Wang、Xiu-Yan Dong

  DOI：10.14233/ajchem.2014.17468

  日期：——

  Four new methoxy-substituted Salamo-type bisoxime compounds 6,6-dimethoxy-2,2-[(propylene-1,3-diyldioxy)bis(nitrilo-methylidyne)]diphenol (H2L1), 6,6-dimethoxy-2,2-[(butylene-1,4-diyldioxy)bis(nitrilomethylidyne)]diphenol (H2L2), 6,6-dimethoxy-2,2-[(propane-1,5-diyldioxy)bis(nitrilome-thylidyne)]diphenol (HH2L3) and 6,6-dimethoxy-2,2-[(hexane-1,6-diyldioxy)bis(nitrilo-methylidyne)]diphenol (H2L4) have been synthesized through condensation reactions under hot ethanol medium, respectively and characterized by elemental analyses, IR, UV-visible and 1H NMR spectra.

  四种新的甲氧基取代的萨拉莫型双肟化合物6,6-二甲氧基-2,2-[(丙烯-1,3-二基二氧基)双(次氮基亚甲基)]联苯酚(H2L1)、6,6-二甲氧基-2、 2-[(丁烯-1,4-二基二氧基)双(次氮基亚甲基)]联苯酚(H2L2)、6,6-二甲氧基-2,2-[(丙烷-1,5-二基二氧基)双(次氮基亚甲基)]联苯酚(HH2L3)和6,6-二甲氧基-2,2-[(己烷-1,6-二基二氧基)双(次氮基亚甲基)]联苯酚(H2L4)分别在热乙醇介质下通过缩合反应合成，并表征为元素分析、红外光谱、紫外-可见光谱和 1H NMR 光谱。
• Synthesis and Characterization of Salamo-type Bisoximes Based on 3-Ethoxysalicyladehyde and Bis(aminooxy)alkane
  作者：Gang Li、Jian-Chun Ma、Zong-Li Ren、Wei-Min Zhou、Li Wang、Na Wen

  DOI：10.14233/ajchem.2015.17557

  日期：——

  A series of ethoxy-substituted Salamo-type bisoximes H2L1-H2L4 have been synthesized from 3-ethoxysalicyladehyde and 1,3-bis(aminooxy)propane, 1,4-bis(aminooxy)butane, 1,5-bis(aminooxy)pentane or 1,6-bis(aminooxy)hexane in hot ethanol medium, respectively and characterized by elemental analyses, IR, UV-visible spectra and 1H NMR spectroscopy. Salamo-type compounds are conducive to coordinate experiments and construct supramolecular complexes.

  在热乙醇介质中，分别从 3-乙氧基水杨醛和 1,3-双（氨基氧基）丙烷、1,4-双（氨基氧基）丁烷、1,5-双（氨基氧基）戊烷或 1,6-双（氨基氧基）己烷合成了一系列乙氧基取代的萨拉莫型双肟 H2L1-H2L4，并通过元素分析、红外光谱、紫外可见光谱和 1H NMR 光谱进行了表征。萨拉莫类化合物有利于进行配位实验和构建超分子复合物。
• Synthesis and Characterization of Multihalogen Substituted Salamo-Type Bisoximes
  作者：Yu-Hua Yang、Xiu-Yan Dong、Yu-Jie Zhang、Gang Li、Meng-Meng Zhao

  DOI：10.14233/ajchem.2014.15925

  日期：——

  Four tetrahalogen substituted Salamo-type bisoximes H2L1-H2L4 have been synthesized from 3-bromo-5-chloro-2-hydroxybenzaldehyde and 1,3-bis(aminooxy)propane, 1,4-bis(aminooxy)butane, 1,5-bis(aminooxy)pentane or 1,6-bis(aminooxy)hexane in ethanol solution, respectively and characterized by elemental analyses as well as IR, UV-visible and 1H NMR spectroscopy.

  四种四卤素取代的萨拉莫型双氧肟 H2L1-H2L4 分别由 3-溴-5-氯-2-羟基苯甲醛和乙醇溶液中的 1,3-双（氨基氧基）丙烷、1,4-双（氨基氧基）丁烷、1,5-双（氨基氧基）戊烷或 1,6-双（氨基氧基）己烷合成，并通过元素分析以及红外光谱、紫外可见光谱和 1H NMR 光谱进行了表征。
• Uracil-Directed Ligand Tethering:  An Efficient Strategy for Uracil DNA Glycosylase (UNG) Inhibitor Development
  作者：Yu Lin Jiang、Daniel J. Krosky、Lauren Seiple、James T. Stivers

  DOI：10.1021/ja055846n

  日期：2005.12.1

  Uracil DNA glycosylase (UNG) is an important DNA repair enzyme that recognizes and excises uracil bases in DNA using an extrahelical recognition mechanism. It is emerging as a desirable target for small-molecule inhibitors given its key role in a wide range of biological processes including the generation of antibody diversity, DNA replication in a number of viruses, and the formation of DNA strand breaks during anticancer drug therapy. To accelerate the discovery of inhibitors of UNG we have developed a uracil-directed ligand tethering strategy. In this efficient approach, a uracil aldehyde ligand is tethered via alkyloxyamine linker chemistry to a diverse array of aldehyde binding elements. Thus, the mechanism of extrahelical recognition of the uracil ligand is exploited to target the UNG active site, and alkyloxyamine linker tethering is used to randomly explore peripheral binding pockets. Since no compound purification is required, this approach rapidly identified the first small-molecule inhibitors of human UNG with micromolar to submicromolar binding affinities. In a surprising result, these uracil-based ligands are found not only to bind to the active site but also to bind to a second uncompetitive site. The weaker uncompetitive site suggests the existence of a transient binding site for uracil during the multistep extrahelical recognition mechanism. This very general inhibitor design strategy can be easily adapted to target other enzymes that recognize nucleobases, including other DNA repair enzymes that recognize other types of extrahelical DNA bases.