3-(2-(diethylamino)acetamido)benzoic acid | 1357620-03-1

• 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: 3-(2-(diethylamino)acetamido)benzoic acid
• 英文别名: 3-[[2-(Diethylamino)acetyl]amino]benzoic acid；3-[[2-(diethylamino)acetyl]amino]benzoic acid
• CAS: 1357620-03-1
• 化学式: C₁₃H₁₈N₂O₃
• 分子量: 250.298
• InChiKey: FBPRCFZIFHYLTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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 、 3-(2-(diethylamino)acetamido)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92%的产率得到
  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-氨基苯甲酸苄酯 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 5.0h， 生成 3-(2-(diethylamino)acetamido)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

• Design, synthesis, antimycobacterial activity and molecular docking studies of novel 3- (N-substituted glycinamido) benzoic acid analogues as anti tubercular agents
  作者：Hymavathi Veeravarapu、Mohan Tirumalasetty、SonyPriya Kurati、Umarani Wunnava、Murali Krishna Kumar Muthyala

  DOI：10.1016/j.bmcl.2020.127603

  日期：2020.12

  identified mycolic acid methyl transferase (MmaA1) enzyme inhibitors as potential antitubercular agents using in silico modelling techniques. In continuation of that study, we synthesised a series of novel 3- (N-substituted glycinamido) benzoic acid derivatives with an aim to optimise the lead molecule. The newly synthesised compounds were evaluated for their in vitro antimycobacterial activity against M.

  我们最近使用计算机模拟技术将霉菌酸甲基转移酶（MmaA1）酶抑制剂确定为潜在的抗结核药。在继续这项研究的过程中，我们合成了一系列新颖的3-（N-取代的甘氨酸酰胺基）苯甲酸衍生物，旨在优化铅分子。评价新合成的化合物对结核分枝杆菌H 37的体外抗分枝杆菌活性。收视率 其中，5种化合物A3，A4，A5，A6和A10表现出最强的活性，MIC值为1.6μg/ ml。进行了进一步的分子对接研究以研究配体与MmaA1蛋白的结合模式。对接研究显示，配体与MmaA1蛋白的催化位点残基TRP30，TYR 32，GLY 71，TRP 74，GLY 76，ALA 77和GLU 136产生强相互作用。还使用计算工具研究了化合物的药物似性和前导性性质。结果，在硅片和体外研究表明，这些新型化合物可用于治疗肺结核有利于引线。
• 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.