N-(4-((propylamino)methyl)-3-hydroxyphenyl)acetamide | 1414782-06-1

• 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: N-(4-((propylamino)methyl)-3-hydroxyphenyl)acetamide
• 英文别名: N-(3-hydroxy-4-((propylamino)methyl)phenyl)acetamide；N-[3-hydroxy-4-(propylaminomethyl)phenyl]acetamide
• CAS: 1414782-06-1
• 化学式: C₁₂H₁₈N₂O₂
• 分子量: 222.287
• InChiKey: NQLXEDLBROQYDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  61.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-((propylamino)methyl)-3-hydroxyphenyl)acetamide 在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 N-(4-((propylamino)methyl)-3-hydroxyphenyl)-7-chloro-4-aminoquinoline
  参考文献：
  名称：

  Mimicking the Intramolecular Hydrogen Bond: Synthesis, Biological Evaluation, and Molecular Modeling of Benzoxazines and Quinazolines as Potential Antimalarial Agents

  摘要：

  The intramolecular hydrogen bond formed between a protonated amine and a neighboring H-bond acceptor group in the side chain of amodiaquine and isoquine is thought to play an important role in their antimalarial activities. Here we describe isoquine-based compounds in which the intramolecular H-bond is mimicked by a methylene linker. The antimalarial activities of the resulting benzoxazines, their isosteric tetrahydroquinazoline derivatives, and febrifugine-based 1,3-quinazolin-4-ones were examined in vitro (against Plasmodium falciparum) and in vivo (against Plasmodium berghei). Compounds 6b,c caused modest inhibition of chloroquine transport via the parasite's "chloroquine resistance transporter" (PfCRT) in a Xenopus laevis oocyte expression system. In silico predictions and experimental evaluation of selected drug-like properties were also performed on compounds 6b,c. Compound 6c emerged from this work as the most promising analogue of the series; it possessed low toxicity and good antimalarial activity when administered orally to P. berghei-infected mice.

  DOI：

  10.1021/jm300831b
• 作为产物：
  描述：

  正丙胺 、 聚合甲醛 、 N-(3-羟基苯基)乙酰胺 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 N-(4-((propylamino)methyl)-3-hydroxyphenyl)acetamide
  参考文献：
  名称：

  一些7-氯-4-氨基喹啉新曼尼希碱的合成及抗疟活性研究。

  摘要：

  通过用曼尼希侧链上的不同脂族/芳族杂环伯氨基部分选择性修饰异喹啉的脂族二乙基氨基官能团，制得7-氯-4-氨基喹啉曼尼希碱的新衍生物。合成的化合物通过其分析和光谱数据进行表征，并针对恶性疟原虫的氯喹敏感3D7菌株进行体外抗疟活性筛选。所有化合物在测试剂量下均表现出体外抗疟活性。但是，它比标准参考药物氯喹要少得多。在合成的化合物中，具有环己基（2f），甲基（2c）取代的化合物显示出比被正辛基（2a），丙基（2b），3-氨丙基（2d）和呋喃-2-基甲基（2e）取代的化合物更好的活性氨基甲基侧链上的部分。

  DOI：

  10.2174/1573406411309030008

文献信息

• Mimicking the Intramolecular Hydrogen Bond: Synthesis, Biological Evaluation, and Molecular Modeling of Benzoxazines and Quinazolines as Potential Antimalarial Agents
  作者：Sandra Gemma、Caterina Camodeca、Margherita Brindisi、Simone Brogi、Gagan Kukreja、Sanil Kunjir、Emanuele Gabellieri、Leonardo Lucantoni、Annette Habluetzel、Donatella Taramelli、Nicoletta Basilico、Roberta Gualdani、Francesco Tadini-Buoninsegni、Gianluca Bartolommei、Maria Rosa Moncelli、Rowena E. Martin、Robert L. Summers、Stefania Lamponi、Luisa Savini、Isabella Fiorini、Massimo Valoti、Ettore Novellino、Giuseppe Campiani、Stefania Butini

  DOI：10.1021/jm300831b

  日期：2012.12.13

  The intramolecular hydrogen bond formed between a protonated amine and a neighboring H-bond acceptor group in the side chain of amodiaquine and isoquine is thought to play an important role in their antimalarial activities. Here we describe isoquine-based compounds in which the intramolecular H-bond is mimicked by a methylene linker. The antimalarial activities of the resulting benzoxazines, their isosteric tetrahydroquinazoline derivatives, and febrifugine-based 1,3-quinazolin-4-ones were examined in vitro (against Plasmodium falciparum) and in vivo (against Plasmodium berghei). Compounds 6b,c caused modest inhibition of chloroquine transport via the parasite's "chloroquine resistance transporter" (PfCRT) in a Xenopus laevis oocyte expression system. In silico predictions and experimental evaluation of selected drug-like properties were also performed on compounds 6b,c. Compound 6c emerged from this work as the most promising analogue of the series; it possessed low toxicity and good antimalarial activity when administered orally to P. berghei-infected mice.
• Synthesis and Antimalarial Activity Study of Some New Mannich Bases of 7-Chloro-4-Aminoquinoline
  作者：Susanta Roy、Dipak Chetia、Mithun Rudrapal、Anil Prakash

  DOI：10.2174/1573406411309030008

  日期：2013.2.1

  synthesized compounds, compounds with cyclohexyl (2f), methyl (2c) substitutions showed better activity than compounds substituted with n-octyl (2a), propyl (2b), 3-aminopropyl (2d) and furan-2- ylmethyl (2e) moieties at aminomethyl side chain. The results clearly demonstrate that the compound substituted with saturated cycloalkyl moiety (cyclohexyl) exhibited to some extent increased activity as compared

  通过用曼尼希侧链上的不同脂族/芳族杂环伯氨基部分选择性修饰异喹啉的脂族二乙基氨基官能团，制得7-氯-4-氨基喹啉曼尼希碱的新衍生物。合成的化合物通过其分析和光谱数据进行表征，并针对恶性疟原虫的氯喹敏感3D7菌株进行体外抗疟活性筛选。所有化合物在测试剂量下均表现出体外抗疟活性。但是，它比标准参考药物氯喹要少得多。在合成的化合物中，具有环己基（2f），甲基（2c）取代的化合物显示出比被正辛基（2a），丙基（2b），3-氨丙基（2d）和呋喃-2-基甲基（2e）取代的化合物更好的活性氨基甲基侧链上的部分。