4-(3-(dimethylamino)propylcarbamoyl)benzoic acid | 1155168-52-7

• 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: 4-(3-(dimethylamino)propylcarbamoyl)benzoic acid
• 英文别名: 4-[[3-(Dimethylamino)propyl]carbamoyl]benzoic acid；4-[3-(dimethylamino)propylcarbamoyl]benzoic acid
• CAS: 1155168-52-7
• 化学式: C₁₃H₁₈N₂O₃
• mdl: MFCD12070357
• 分子量: 250.298
• InChiKey: VJGRIOGJIZSXJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-amino-5-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)acetamide 、 4-(3-(dimethylamino)propylcarbamoyl)benzoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 1-羟基苯并三唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.03h， 以96%的产率得到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
• 作为产物：
  描述：

  benzyl 4-chloroformylbenzoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 23.0h， 生成 4-(3-(dimethylamino)propylcarbamoyl)benzoic acid
  参考文献：
  名称：

  Synthesis of benzoic acids and polybenzamides containing tertiary alkylamino functionality

  摘要：

  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.

  DOI：

  10.1016/j.tet.2011.12.030

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.