4-[2-(3-methoxyphenyl)acetylamino]benzoic acid | 1016524-39-2

• 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-[2-(3-methoxyphenyl)acetylamino]benzoic acid
• 英文别名: 4-[[2-(3-Methoxyphenyl)acetyl]amino]benzoic acid
• CAS: 1016524-39-2
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: CEZSEBCBEMWKMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[2-(3-methoxyphenyl)acetylamino]benzoic acid 在 N-甲基吗啉 、 氯甲酸乙酯 、 羟胺 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 为溶剂， 反应 0.17h， 生成 N-hydroxy-4-[2-(3-methoxyphenyl)acetamido]benzamide
  参考文献：
  名称：

  Synthesis of aminophenylhydroxamate and aminobenzylhydroxamate derivatives and in vitro screening for antiparasitic and histone deacetylase inhibitory activity

  摘要：

  A series of aminophenylhydroxamates and aminobenzylhydroxamates were synthesized and screened for their antiparasitic activity against Leishmania, Trypanosoma, and Toxoplasma. Their anti-histone deacetylase (HDAC) potency was determined. Moderate to no antileishmanial or antitrypanosomal activity was found (IC50 > 10 mu M) that contrast with the highly efficient anti-Toxoplasma activity (IC50 < 1.0 mu M) of these compounds. The antiparasitic activity of the synthetized compounds correlates well with their HDAC inhibitory activity. The best-performing compound (named 363) express a high anti-HDAC6 inhibitory activity (IC50 of 0.045 +/- 0.015 mu M) a moderate cytotoxicity and a high anti-Toxoplasma activity in the range of known anti-Toxoplasma compounds (IC50 of 0.35-2.25 mu M). The calculated selectivity index (10-300 using different human cell lines) of the compound 363 makes it a lead compound for the future development of anti-Toxoplasma molecules.

  DOI：

  10.1016/j.ijpddr.2018.01.002
• 作为产物：
  描述：

  3-甲氧基苯基乙酰氯 在 三乙胺 、 lithium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 4-[2-(3-methoxyphenyl)acetylamino]benzoic acid
  参考文献：
  名称：

  Synthesis of aminophenylhydroxamate and aminobenzylhydroxamate derivatives and in vitro screening for antiparasitic and histone deacetylase inhibitory activity

  摘要：

  A series of aminophenylhydroxamates and aminobenzylhydroxamates were synthesized and screened for their antiparasitic activity against Leishmania, Trypanosoma, and Toxoplasma. Their anti-histone deacetylase (HDAC) potency was determined. Moderate to no antileishmanial or antitrypanosomal activity was found (IC50 > 10 mu M) that contrast with the highly efficient anti-Toxoplasma activity (IC50 < 1.0 mu M) of these compounds. The antiparasitic activity of the synthetized compounds correlates well with their HDAC inhibitory activity. The best-performing compound (named 363) express a high anti-HDAC6 inhibitory activity (IC50 of 0.045 +/- 0.015 mu M) a moderate cytotoxicity and a high anti-Toxoplasma activity in the range of known anti-Toxoplasma compounds (IC50 of 0.35-2.25 mu M). The calculated selectivity index (10-300 using different human cell lines) of the compound 363 makes it a lead compound for the future development of anti-Toxoplasma molecules.

  DOI：

  10.1016/j.ijpddr.2018.01.002

文献信息

• An improved method of amide synthesis using acyl chlorides
  作者：Li Zhang、Xiao-jun Wang、Jing Wang、Nelu Grinberg、DhileepKumar Krishnamurthy、Chris H. Senanayake

  DOI：10.1016/j.tetlet.2009.03.220

  日期：2009.6

  A simple, mild and highly efficient condition for amide synthesis from acyl chlorides has been developed to minimize hydrolysis, racemization and other side reactions. This method should expand capabilities in the peptide coupling area.

  已经开发了一种简单，温和且高效的条件，用于从酰氯合成酰胺，以最大程度地减少水解，外消旋作用和其他副反应。该方法应扩大肽偶联区域的能力。