1-(2,5-dimethoxy-4-n-propylthiophenyl)-2-nitro-1-butene | 849919-73-9

• 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: 1-(2,5-dimethoxy-4-n-propylthiophenyl)-2-nitro-1-butene
• 英文别名: 1,4-dimethoxy-2-(2-nitrobut-1-enyl)-5-propylsulfanylbenzene
• CAS: 849919-73-9
• 化学式: C₁₅H₂₁NO₄S
• 分子量: 311.402
• InChiKey: SDRNHQYLEZTYDI-UHFFFAOYSA-N

物化性质

• 熔点：
  55-56 °C(Solv: ethanol (64-17-5))
• 沸点：
  448.9±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61.6
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(2,5-dimethoxy-4-n-propylthiophenyl)-2-nitro-1-butene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 生成 [1-(2,5-Dimethoxy-4-propylsulfanyl-benzyl)-propyl]-methyl-amine
  参考文献：
  名称：

  Sulfur-Substituted α-Alkyl Phenethylamines as Selective and Reversible MAO-A Inhibitors:  Biological Activities, CoMFA Analysis, and Active Site Modeling

  摘要：

  A series of phenethylamine derivatives with various ring substituents and with or without N-methyl and/or C-alpha methyl or ethyl groups was synthesized and assayed for their ability reversibly to inhibit monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). Several compounds. showed potent and selective MAO-A inhibitory activity (IC50 in the submicromolar range) but none showed appreciable activity toward MAO-B. A three-dimensional quantitative structure-activity relationship study for MAO-A inhibition was performed on the series using comparative molecular field analysis (CoMFA). The resulting model gave a cross-validated q(2) of 0.72 and showed that in this series of compounds steric properties of the substituents were more important than electrostatic effects. Molecular modeling based on the recently published crystal structure of inhibitor-bound MAO-A provided detailed evidence for specific interactions of the ligands with the enzyme, supported by previous references and consistent with results from the CoMFA. On the basis of these results, structural determinants for selectivity of substituted amphetamines for MAO-A are discussed.

  DOI：

  10.1021/jm0493109
• 作为产物：
  描述：

  1,4-dimethoxy-2-n-propylthiobenzene 在 N,N'-二甲基乙二胺 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 48.25h， 生成 1-(2,5-dimethoxy-4-n-propylthiophenyl)-2-nitro-1-butene
  参考文献：
  名称：

  Sulfur-Substituted α-Alkyl Phenethylamines as Selective and Reversible MAO-A Inhibitors:  Biological Activities, CoMFA Analysis, and Active Site Modeling

  摘要：

  A series of phenethylamine derivatives with various ring substituents and with or without N-methyl and/or C-alpha methyl or ethyl groups was synthesized and assayed for their ability reversibly to inhibit monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). Several compounds. showed potent and selective MAO-A inhibitory activity (IC50 in the submicromolar range) but none showed appreciable activity toward MAO-B. A three-dimensional quantitative structure-activity relationship study for MAO-A inhibition was performed on the series using comparative molecular field analysis (CoMFA). The resulting model gave a cross-validated q(2) of 0.72 and showed that in this series of compounds steric properties of the substituents were more important than electrostatic effects. Molecular modeling based on the recently published crystal structure of inhibitor-bound MAO-A provided detailed evidence for specific interactions of the ligands with the enzyme, supported by previous references and consistent with results from the CoMFA. On the basis of these results, structural determinants for selectivity of substituted amphetamines for MAO-A are discussed.

  DOI：

  10.1021/jm0493109