Benzenesulfonamide,N-[3-[[(4-hydroxy-3-methoxyphenyl)methyl]propylamino]propyl]-2-nitro- | 906748-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Benzenesulfonamide,N-[3-[[(4-hydroxy-3-methoxyphenyl)methyl]propylamino]propyl]-2-nitro-
• 英文别名: N-{3-[(4-Hydroxy-3-methoxy-benzyl)-propyl-amino]-propyl}-2-nitro-benzenesulfonamide
• CAS: 906748-07-0
• 化学式: C₂₀H₂₇N₃O₆S
• 分子量: 437.517
• InChiKey: BBYKZYPRTPEFCX-UHFFFAOYSA-N

物化性质

• 沸点：
  604.0±65.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  30.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  122.01
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Benzenesulfonamide,N-[3-[[(4-hydroxy-3-methoxyphenyl)methyl]propylamino]propyl]-2-nitro- 在 caesium carbonate 、 苯硫酚 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 4.0h， 生成 2-methoxy-4-({[3-(2-methoxy-7-trifluoromethyl-acridin-9-ylamino)-propyl]-propyl-amino}-methyl)-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：

  Propanamide, N-[3-[[(2-nitrophenyl)sulfonyl]amino]propyl]- 在 dimethyl sulfide borane 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 Benzenesulfonamide,N-[3-[[(4-hydroxy-3-methoxyphenyl)methyl]propylamino]propyl]-2-nitro-
  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