N-(3-acetamido-5-((tert-butyldimethylsilyloxy)methyl)phenyl)-N'-(3-(dimethylamino)propyl) terephthalamide | 1357620-17-7

• 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: N-(3-acetamido-5-((tert-butyldimethylsilyloxy)methyl)phenyl)-N'-(3-(dimethylamino)propyl) terephthalamide
• 英文别名: 4-N-[3-acetamido-5-[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]-1-N-[3-(dimethylamino)propyl]benzene-1,4-dicarboxamide
• CAS: 1357620-17-7
• 化学式: C₂₈H₄₂N₄O₄Si
• 分子量: 526.751
• InChiKey: PHHQUWUQZDXGHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  99.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3-acetamido-5-((tert-butyldimethylsilyloxy)methyl)phenyl)-N'-(3-(dimethylamino)propyl) terephthalamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以94%的产率得到N-(3-acetamido-5-(hydroxymethyl)phenyl)-N'-(3-(dimethylamino)propyl)-terephthalamide
  参考文献：
  名称：

  Synthesis and biological activity of benzamide DNA minor groove binders

  摘要：

  A range of di- and triaryl benzamides were synthesised to investigate the effect of the presence and nature of a polar sidechain, bonding and substitution patterns and functionalisation of benzylic substituents. These compounds were tested for their antiproliferative activity as well as their DNA binding activity. The most active compounds in all assays were unsymmetrical triaryl benzamides with a bulky or alkylating benzylic substituent and a polar amino sidechain. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.090
• 作为产物：
  描述：

  3-氨基-5-硝基苯甲醇 在 咪唑 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.03h， 生成 N-(3-acetamido-5-((tert-butyldimethylsilyloxy)methyl)phenyl)-N'-(3-(dimethylamino)propyl) terephthalamide
  参考文献：
  名称：

  Synthesis and biological activity of benzamide DNA minor groove binders

  摘要：

  A range of di- and triaryl benzamides were synthesised to investigate the effect of the presence and nature of a polar sidechain, bonding and substitution patterns and functionalisation of benzylic substituents. These compounds were tested for their antiproliferative activity as well as their DNA binding activity. The most active compounds in all assays were unsymmetrical triaryl benzamides with a bulky or alkylating benzylic substituent and a polar amino sidechain. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.090

文献信息

• Synthesis of benzoic acids and polybenzamides containing tertiary alkylamino functionality
  作者：Gul Shahzada Khan、Benjamin D. Dickson、David Barker

  DOI：10.1016/j.tet.2011.12.030

  日期：2012.2

  The high-yielding and easily scalable synthesis of a number of benzoic acids bearing a tertiary alkylamino functionality has been achieved. The flexible synthesis began from readily available aminobenzoic acids or terephthaloyl chloride and requires almost no chromatography. Coupling of the synthesised amino acids to a range of substituted anilines was achieved when utilizing a specific combination of DIC, HOBt and DMAP. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and biological activity of benzamide DNA minor groove binders
  作者：Gul Shahzada Khan、Lisa I. Pilkington、David Barker

  DOI：10.1016/j.bmcl.2015.12.090

  日期：2016.2

  A range of di- and triaryl benzamides were synthesised to investigate the effect of the presence and nature of a polar sidechain, bonding and substitution patterns and functionalisation of benzylic substituents. These compounds were tested for their antiproliferative activity as well as their DNA binding activity. The most active compounds in all assays were unsymmetrical triaryl benzamides with a bulky or alkylating benzylic substituent and a polar amino sidechain. (C) 2015 Elsevier Ltd. All rights reserved.