4-(4-bromophenoxy)phthalonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(4-bromophenoxy)phthalonitrile
• 英文别名: 4-(4-bromophenoxy)benzene-1,2-dicarbonitrile
• 化学式: C₁₄H₇BrN₂O
• 分子量: 299.126
• InChiKey: ZHWODKAGCZSVQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-bromophenoxy)phthalonitrile 在 sodium ethanolate 、 硝酸 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以48%的产率得到5-(4-bromophenoxy)phthalimide
  参考文献：
  名称：

  Inhibition of monoamine oxidase by C5-substituted phthalimide analogues

  摘要：

  Literature reports that isatin as well as C5- and C6-substituted isatin analogues are reversible inhibitors of human monoamine oxidase (MAO) A and B. In general, C5- and C6-substitution of isatin leads to enhanced binding affinity to both MAO isozymes compared to isatin and in most instances result in selective binding to the MAO-B isoform. Crystallographic and modeling studies suggest that the isatin ring binds to the substrate cavities of MAO-A and -B and is stabilized by hydrogen bond interactions between the NH and the C2 carbonyl oxygen of the dioxoindolyl moiety and water molecules present in the substrate cavities of MAO-A and -B. Based on these observations and the close structural resemblances between isatin and its phthalimide isomer, a series of phthalimide analogues were synthesized and evaluated as MAO inhibitors. While phthalimide and N-aryl-substituted phthalimides were found to be weak MAO inhibitors, phthalimide homologues containing C5 substituents were potent reversible inhibitors of recombinant human MAO-B with IC(50) values ranging from 0.007 to 2.5 mu M and moderately potent reversible inhibitors of recombinant human MAO-A with IC(50) values ranging from 0.22 to 9.0 mu M. By employing molecular docking the importance of hydrogen bonding between the active sites of MAO-A and -B and the phthalimide inhibitors are highlighted. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.070
• 作为产物：
  描述：

  4-溴苯酚 、 4-硝基邻苯二甲腈 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以71%的产率得到4-(4-bromophenoxy)phthalonitrile
  参考文献：
  名称：

  C4取代的邻苯二甲腈对单胺氧化酶的抑制作用

  摘要：

  最近有报道称，一系列C5取代的邻苯二甲酰亚胺是重组人单胺氧化酶（MAO）B的强效可逆抑制剂。建模研究表明，邻苯二甲酰亚胺环与MAO-B底物腔的极性区域形成许多极性相互作用，而C5侧链延伸至范德华相互作用，并通过范德华相互作用与酶进入腔的疏水区相互作用。与两个腔体的相互作用似乎是高亲和力结合的要求。在本研究中，我们已经研究了一系列C4取代的邻苯二甲腈作为潜在的人MAO抑制剂的类似物。发现邻苯二甲腈是高度有效的可逆MAO-B抑制剂，大多数类似物的IC 50均高数值在低nM范围内。邻苯二甲腈也与人MAO-A相互作用，尽管与MAO-B相比具有较低的结合亲和力。模型研究表明，邻苯二甲腈与MAO-B的高结合亲和力可能至少部分取决于腈官能团与酶底物腔之间极性相互作用的形成。对苯甲腈同系物系列的检查确定，对于相应的苯甲腈部分，邻苯二甲腈部分对MAO-B的抑制作用最佳，而与C4取代的苯甲腈相比，C3取代的苯

  DOI：

  10.1016/j.bioorg.2011.10.003

文献信息

• Monoamine oxidase inhibition by C4-substituted phthalonitriles
  作者：Clarina I. Manley-King、Jacobus J. Bergh、Jacobus P. Petzer

  DOI：10.1016/j.bioorg.2011.10.003

  日期：2012.2

  studies suggested that the phthalimide ring forms numerous polar interactions with the polar region of the MAO-B substrate cavity while the C5 side chain extends to, and interacts via Van der Waals interactions with the hydrophobic regions of the enzyme entrance cavity. Interactions with both cavities appear to be requirements for high affinity binding. In the present study we have examined an analogs series

  最近有报道称，一系列C5取代的邻苯二甲酰亚胺是重组人单胺氧化酶（MAO）B的强效可逆抑制剂。建模研究表明，邻苯二甲酰亚胺环与MAO-B底物腔的极性区域形成许多极性相互作用，而C5侧链延伸至范德华相互作用，并通过范德华相互作用与酶进入腔的疏水区相互作用。与两个腔体的相互作用似乎是高亲和力结合的要求。在本研究中，我们已经研究了一系列C4取代的邻苯二甲腈作为潜在的人MAO抑制剂的类似物。发现邻苯二甲腈是高度有效的可逆MAO-B抑制剂，大多数类似物的IC 50均高数值在低nM范围内。邻苯二甲腈也与人MAO-A相互作用，尽管与MAO-B相比具有较低的结合亲和力。模型研究表明，邻苯二甲腈与MAO-B的高结合亲和力可能至少部分取决于腈官能团与酶底物腔之间极性相互作用的形成。对苯甲腈同系物系列的检查确定，对于相应的苯甲腈部分，邻苯二甲腈部分对MAO-B的抑制作用最佳，而与C4取代的苯甲腈相比，C3取代的苯
• Tetrakis(4-bromophenoxy)phthalocyanine, its metal complexes, and their sulfonated derivatives: the synthesis and spectral properties
  作者：A. S. Vashurin、T. V. Tikhomirova、A. A. Filippova、N. A. Futerman、V. E. Maizlish、Yu. S. Marfin

  DOI：10.1007/s11172-020-2909-1

  日期：2020.7

  Tetrakis(4-bromophenoxy)phthalocyanine and its metal complexes (M = Mg, Co, Cu, Zn) were synthesized. Sulfochlorination of these compounds followed by hydrolysis of the sulfochlorides gave tetrakis(2-sulfo-4-bromophenoxy)phthalocyanine and corresponding sulfonated metallophthalocyanines (except M = Cu). Spectral properties of the compounds synthesized were investigated. It was shown that the introduction

  合成了四（4-溴苯氧基）酞菁及其金属配合物（M = Mg、Co、Cu、Zn）。这些化合物的磺氯化作用，然后是磺氯化物的水解，得到四（2-磺基-4-溴苯氧基）酞菁和相应的磺化金属酞菁（M = Cu 除外）。研究了合成化合物的光谱特性。结果表明，引入磺基会导致 DMF 中记录的吸收光谱中 Q 带的红移，以及硫酸中记录的吸收光谱中 Q 带的低色移。
• AROMATIC ETHER AND ALKYNYL CONTAINING PHTHALONITRILES
  申请人：Laskoski Matthew

  公开号：US20110288254A1

  公开（公告）日：2011-11-24

  Compounds having the formulas below. R is an aromatic-containing group. Each M is an alkali metal. Each m is a positive integer. The value of n is a positive integer. The value p is 0 or 1. If p is 0 then n is 1. A thermoset made by curing a composition containing the below phthalonitrile monomers. A method of reacting a diphenyl acetylene compound with an excess of an aromatic diol in the presence of an alkali metal carbonate to form the above oligomer. A method of reacting a phenoxyphthalonitrile with an acetylene compound to form the phthalonitrile monomer below.

  具有以下化学式的化合物。其中R是含芳香基团的基团。每个M是一种碱金属。每个m是正整数。n的值为正整数。p的值为0或1。如果p为0，则n为1。通过固化含有以下邻苯二腈单体的组合物制成的热固性材料。一种方法是在碱金属碳酸盐的存在下，将二苯乙炔化合物与过量的芳香二醇反应，形成上述寡聚物。一种方法是将苯氧基邻苯二腈与乙炔化合物反应，形成以下邻苯二腈单体。
• Phthalocyanine–titanate nanotubes: a promising nanocarrier detectable by optical imaging in the so-called imaging window
  作者：J. Paris、Y. Bernhard、J. Boudon、O. Heintz、N. Millot、R. A. Decréau

  DOI：10.1039/c4ra13988g

  日期：——

  TiONts–phthalocyanine nanohybrids (150 nm long, 450 Pc per TiONts) combine an efficient optical probe and a promising nanovector. The organic coating was covalently attached onto TiONts in a step-by-step approach with a thorough characterization at each step.

  TiONts-酞菁纳米杂化物（每个TiONts长150纳米，含450个Pc）结合了高效的光学探针和有前途的纳米载体。有机涂层通过逐步方法与TiONts共价结合，每一步都进行了彻底的表征。
• Magneto-optical nanomaterials: a SPIO–phthalocyanine scaffold built step-by-step towards bimodal imaging
  作者：Julien Boudon、Jérémy Paris、Yann Bernhard、Elena Popova、Richard A. Decréau、Nadine Millot

  DOI：10.1039/c3cc41898g

  日期：——

  A SPIO–phthalocyanine nanohybrid is developed as a bimodal contrast agent for Optical and Magnetic Resonance Imaging. The organic coating was covalently attached onto SPIO in a step-by-step approach. Each coated-SPIO was thoroughly characterized. The hydrodynamic size of the SPIO–Pc is ca. 60 nm with a coverage of ca. 690 Pc/SPIO.

  我们开发了一种 SPIO酞菁纳米杂化物，作为光学和磁共振成像的双模造影剂。有机涂层通过共价方式逐步附着在 SPIO 上。对每种涂覆的 SPIO 都进行了全面的表征。SPIOâPc 的流体力学尺寸约为 60 nm，覆盖率约为 690 Pc/SPIO。