3-(4-bromobenzyloxy)benzonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-bromobenzyloxy)benzonitrile
• 英文别名: 3-((4-Bromobenzyl)oxy)benzonitrile；3-[(4-bromophenyl)methoxy]benzonitrile
• 化学式: C₁₄H₁₀BrNO
• mdl: MFCD06629410
• 分子量: 288.143
• InChiKey: NXAQGAGXVWWKJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-bromobenzyloxy)benzonitrile 在 lithium hexamethyldisilazane 作用下， 生成 3-[(4-Bromophenyl)methoxy]benzamidine
  参考文献：
  名称：

  Design, synthesis and evaluation of potential inhibitors of HIV gp120–CD4 interactions

  摘要：

  This paper describes an approach to prevent HIV-cell fusion by disrupting the interaction between HIV protein gp120 and CD4 receptor. The CD4 residues Phe43 and Arg59 make important interactions with gp120. Small molecule analogues were made to mimic the crucial features of these residues. The analogues were assayed using a cellular 'FIGS' assay to measure inhibition of cell fusion and caused some inhibition. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.091
• 作为产物：
  描述：

  3-氰基苯酚 、 对溴溴苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到3-(4-bromobenzyloxy)benzonitrile
  参考文献：
  名称：

  Design, synthesis and evaluation of potential inhibitors of HIV gp120–CD4 interactions

  摘要：

  This paper describes an approach to prevent HIV-cell fusion by disrupting the interaction between HIV protein gp120 and CD4 receptor. The CD4 residues Phe43 and Arg59 make important interactions with gp120. Small molecule analogues were made to mimic the crucial features of these residues. The analogues were assayed using a cellular 'FIGS' assay to measure inhibition of cell fusion and caused some inhibition. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.091

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
• Design, synthesis and evaluation of potential inhibitors of HIV gp120–CD4 interactions
  作者：Cyrille Boussard、Thomas Klimkait、Naheed Mahmood、Martin Pritchard、Ian H. Gilbert

  DOI：10.1016/j.bmcl.2004.02.091

  日期：2004.5

  This paper describes an approach to prevent HIV-cell fusion by disrupting the interaction between HIV protein gp120 and CD4 receptor. The CD4 residues Phe43 and Arg59 make important interactions with gp120. Small molecule analogues were made to mimic the crucial features of these residues. The analogues were assayed using a cellular 'FIGS' assay to measure inhibition of cell fusion and caused some inhibition. (C) 2004 Elsevier Ltd. All rights reserved.