4-{[(3-Amino-propyl)-ethyl-amino]-methyl}-2-methoxy-phenol | 874813-59-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-{[(3-Amino-propyl)-ethyl-amino]-methyl}-2-methoxy-phenol
• 英文别名: 4-[[3-aminopropyl(ethyl)amino]methyl]-2-methoxyphenol
• CAS: 874813-59-9
• 化学式: C₁₃H₂₂N₂O₂
• 分子量: 238.33
• InChiKey: JZYKKAMWTBNMKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  58.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-{[(3-Amino-propyl)-ethyl-amino]-methyl}-2-methoxy-phenol 、 2-methoxy-9-phenoxy-7-trifluoromethyl-acridine 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 4-({ethyl-[3-(2-methoxy-7-trifluoromethyl-acridin-9-ylamino)-propyl]-amino}-methyl)-2-methoxy-phenol
  参考文献：
  名称：

  Parallel synthesis of 9-aminoacridines and their evaluation against chloroquine-resistant Plasmodium falciparum

  摘要：

  A parallel synthetic strategy to the 9-aminoacridine scaffold of the classical anti-malarial drug quinacrine (2) is presented. The method features a new route to 9-chloroacridines that utilizes triflates of salicylic acid derivatives, which are commercially available in a variety of substitution patterns. The route allows ready variation of the two diversity elements present in this class of molecules: the tricyclic aromatic heterocyclic core, and the disubstituted diamine sidechain. In this study, a library of 175 compounds was designed, although only 93 of the final products had purities acceptable for screening. Impurity was generally due to incomplete removal of 9-acridones (18), a degradation product of the 9-chloroacridine synthetic intermediates. The library was screened against two strains of Plasmodium falciparum, including a model of the drug-resistant parasite, and six novel compounds were found to have IC50 values in the low nanomolar range. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.017
• 作为产物：
  描述：

  N-(3-Ethylamino-propyl)-2-nitro-benzenesulfonamide 在 三乙酰氧基硼氢化钠 、 caesium carbonate 、 苯硫酚 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.0h， 生成 4-{[(3-Amino-propyl)-ethyl-amino]-methyl}-2-methoxy-phenol
  参考文献：
  名称：

  Parallel synthesis of 9-aminoacridines and their evaluation against chloroquine-resistant Plasmodium falciparum

  摘要：

  A parallel synthetic strategy to the 9-aminoacridine scaffold of the classical anti-malarial drug quinacrine (2) is presented. The method features a new route to 9-chloroacridines that utilizes triflates of salicylic acid derivatives, which are commercially available in a variety of substitution patterns. The route allows ready variation of the two diversity elements present in this class of molecules: the tricyclic aromatic heterocyclic core, and the disubstituted diamine sidechain. In this study, a library of 175 compounds was designed, although only 93 of the final products had purities acceptable for screening. Impurity was generally due to incomplete removal of 9-acridones (18), a degradation product of the 9-chloroacridine synthetic intermediates. The library was screened against two strains of Plasmodium falciparum, including a model of the drug-resistant parasite, and six novel compounds were found to have IC50 values in the low nanomolar range. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.017