1-(2,5-dimethoxy-4-methylthiophenyl)-2-nitro-1-propene | 61638-05-9

• 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-methylthiophenyl)-2-nitro-1-propene
• 英文别名: Benzene, 1,4-dimethoxy-5-(methylthio)-2-(2-nitro-1-propenyl)-；1,4-dimethoxy-2-methylsulfanyl-5-(2-nitroprop-1-enyl)benzene
• CAS: 61638-05-9
• 化学式: C₁₂H₁₅NO₄S
• 分子量: 269.321
• InChiKey: ZEZKFCRNWMIAEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2,5-dimethoxy-4-methylthiophenyl)-2-nitro-1-propene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 1-(2,5-二甲氧基-4-甲硫基苯基)-2-氨基丙烷盐酸盐
  参考文献：
  名称：

  拟精神胺的硫类似物

  摘要：

  描述了2，5-二甲氧基-4-甲基硫代苯基乙胺和2，5-二甲氧基-4-甲基硫代苯基异丙胺的合成和物理性质。后一种化合物是拟精神病的苯基异丙基胺2,4,5-三甲氧基苯基异丙基胺和2,5-二甲氧基-4-甲基苯基异丙基胺的硫类似物，其中甲硫基分别取代甲氧基或甲基。预计该化合物的活性约为麦斯卡林的30倍。

  DOI：

  10.1002/jps.2600651040
• 作为产物：
  描述：

  1,4-dimethoxy-2-methylthiobenzene 在 ammonium acetate 作用下， 生成 1-(2,5-dimethoxy-4-methylthiophenyl)-2-nitro-1-propene
  参考文献：
  名称：

  拟精神胺的硫类似物

  摘要：

  描述了2，5-二甲氧基-4-甲基硫代苯基乙胺和2，5-二甲氧基-4-甲基硫代苯基异丙胺的合成和物理性质。后一种化合物是拟精神病的苯基异丙基胺2,4,5-三甲氧基苯基异丙基胺和2,5-二甲氧基-4-甲基苯基异丙基胺的硫类似物，其中甲硫基分别取代甲氧基或甲基。预计该化合物的活性约为麦斯卡林的30倍。

  DOI：

  10.1002/jps.2600651040

文献信息

• Sulfur Analogs of Psychotomimetic Amines
  作者：Alexander T. Shulgin、David E. Nichols

  DOI：10.1002/jps.2600651040

  日期：1976.10

  The syntheses and physical properties are described for 2,5-dimethoxy-4-methylthiophenylethylamine and 2,5-dimethoxy-4-methylthiophenylisopropylamine. The latter compound is the sulfur analog of the psychotomimetic phenylisopropylamines 2,4,5-trimethoxyphenylisopropylamine and 2,5-dimethoxy-4-methylphenylisopropylamine wherein the methylthio group replaces a methoxy group or a methyl group, respectively

  描述了2，5-二甲氧基-4-甲基硫代苯基乙胺和2，5-二甲氧基-4-甲基硫代苯基异丙胺的合成和物理性质。后一种化合物是拟精神病的苯基异丙基胺2,4,5-三甲氧基苯基异丙基胺和2,5-二甲氧基-4-甲基苯基异丙基胺的硫类似物，其中甲硫基分别取代甲氧基或甲基。预计该化合物的活性约为麦斯卡林的30倍。
• [EN] PHENETHYLAMINE DERIVATIVES, COMPOSITIONS, AND METHODS OF USE<br/>[FR] DÉRIVÉS DE PHÉNÉTYLAMINE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：[en]CYBIN IRL LIMITED

  公开号：WO2023156453A1

  公开（公告）日：2023-08-24

  There are disclosed psychedelic and entactogen compounds, the use of such compounds in the treatment of diseases associated with a serotonin receptor or monoamine transporter, 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 receptor or monoamine transporter, such as inflammation, central nervous system (CNS) disorders or psychological disorders with the compounds of the invention.
• Sulfur-Substituted α-Alkyl Phenethylamines as Selective and Reversible MAO-A Inhibitors:  Biological Activities, CoMFA Analysis, and Active Site Modeling
  作者：Alejandra Gallardo-Godoy、Angélica Fierro、Thomas H. McLean、Mariano Castillo、Bruce K. Cassels、Miguel Reyes-Parada、David E. Nichols

  DOI：10.1021/jm0493109

  日期：2005.4.1

  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.