1,4-dimethoxy-2-(pentylthio)benzene | 129658-04-4

• 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: 1,4-dimethoxy-2-(pentylthio)benzene
• 英文别名: 1,4-dimethoxy-2-n-pentylthiobenzene；1,4-Dimethoxy-2-pentylsulfanylbenzene
• CAS: 129658-04-4
• 化学式: C₁₃H₂₀O₂S
• 分子量: 240.367
• InChiKey: LOBNGSKMNCRSNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 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：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-dimethoxy-2-(pentylthio)benzene 在 盐酸 、 lithium aluminium tetrahydride 、 三氯化铝 、 乙酸酐 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.17h， 生成 N-(2-(2,5-dimethoxy-4-(pentylthio)phenyl)ethyl)formamide
  参考文献：
  名称：

  Sindelar, Karel; Holubek, Jiri; Svatek, Emil, Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 3, p. 782 - 796

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-二甲氧基苯磺酰氯 在 盐酸 、 氢氧化钾 、 锌 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 1,4-dimethoxy-2-(pentylthio)benzene
  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

文献信息

• SINDELAR, KAREL;HOLUBEK, JIRI;SVATEK, EMIL;SCHLANGER, JIRI;DLABAC, ANTONI+, COLLECT. CZECHOSL. CHEM. COMMUN., 55,(1990) N, C. 782-796
  作者：SINDELAR, KAREL、HOLUBEK, JIRI、SVATEK, EMIL、SCHLANGER, JIRI、DLABAC, ANTONI+

  DOI：——

  日期：——