2,5-dimethoxy-4-propylsulfanyl-benzaldehyde | 132184-35-1

• 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: 2,5-dimethoxy-4-propylsulfanyl-benzaldehyde
• 英文别名: 2,5-dimethoxy-4-(n-propylthio)benzaldehyde；2,5-dimethoxy-4-n-propylthiobenzaldehyde；Benzaldehyde, 2,5-dimethoxy-4-(propylthio)-；2,5-dimethoxy-4-propylsulfanylbenzaldehyde
• CAS: 132184-35-1
• 化学式: C₁₂H₁₆O₃S
• 分子量: 240.323
• InChiKey: VZQMAHCKOWMLMU-UHFFFAOYSA-N

物化性质

• 熔点：
  78-79 °C(Solv: ethanol (64-17-5))
• 沸点：
  381.6±42.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-dimethoxy-4-propylsulfanyl-benzaldehyde 在 lithium aluminium tetrahydride 、 ammonium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 生成 [2-(2,5-Dimethoxy-4-propylsulfanyl-phenyl)-1-methyl-ethyl]-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：

  N-甲基甲酰苯胺 、 1,4-dimethoxy-2-n-propylthiobenzene 在 三氯氧磷 作用下， 反应 0.25h， 以99%的产率得到2,5-dimethoxy-4-propylsulfanyl-benzaldehyde
  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

• Synthesis of deuterium labeled phenethylamine derivatives
  作者：Ya-Zhu Xu、Chinpiao Chen

  DOI：10.1002/jlcr.1139

  日期：2006.11

  The synthesis of a series of five deuterium labeled phenethylamine derivatives, 4-bromo-2,5-[2H6]-dimethoxyphenethylamine (2C-B), 4-chloro-2,5-[2H6]-dimethoxyphenethylamine (2C-C), 2,5-[2H6]-dimethoxy-4-iodophenethylamine (2C-I), 2,5-[2H6]-dimethoxy-4-ethylthiophenethylamine (2C-T-2) and 2,5-[2H6]-dimethoxy-4-n-propylthiophenethylamine (2C-T-7) from 1,4-[2H6]-dimethoxybenzene is described. The isotopically

  一系列五种氘标记的苯乙胺衍生物的合成，4-溴-2,5-[2H6]-二甲氧基苯乙胺（2C-B），4-氯-2,5-[2H6]-二甲氧基苯乙胺（2C-C）， 2,5-[2H6]-二甲氧基-4-碘苯乙胺 (2C-I)、2,5-[2H6]-二甲氧基-4-乙基噻吩乙胺 (2C-T-2) 和 2,5-[2H6]-二甲氧基-描述了来自 1,4-[2H6]-二甲氧基苯的 4-n-丙基噻吩乙胺 (2C-T-7)。同位素标记的化合物用作气相色谱-质谱 (GC-MS) 分析中的内标。版权所有 © 2006 John Wiley & Sons, Ltd.
• [EN] THERAPEUTIC PHENETHYLAMINE COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSITIONS DE PHÉNÉTHYLAMINE THÉRAPEUTIQUE ET MÉTHODES D'UTILISATION
  申请人：CYBIN IRL LTD

  公开号：WO2022038170A1

  公开（公告）日：2022-02-24

  There are disclosed deuterated 2C-X phenethylamine compounds, the use of such compounds in the treatment of diseases associated with a serotonin 5-HT2 receptor, pharmaceutical compositions such as tablet compositions and kits containing the compounds, methods of delivering the compounds in a mist via inhalation, and methods of treating diseases or disorders associated with a serotonin 5-HT2 receptor, such as central nervous system (CNS) disorders or psychological disorders with the compounds of the invention.

  本文披露了脱氘化的2C-X苯乙胺化合物，以及这些化合物在治疗与5-HT2受体相关的疾病中的应用，包括药用组合物（如片剂组合物）和包含这些化合物的套装，通过雾化吸入途径传递这些化合物的方法，以及使用本发明的化合物治疗与5-HT2受体相关的疾病或疾病的方法，如中枢神经系统（CNS）疾病或心理疾病。