(Z)-2-(4-Bromo-phenyl)-1,3-di-morpholin-4-yl-propenethione | 159298-76-7

• 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: (Z)-2-(4-Bromo-phenyl)-1,3-di-morpholin-4-yl-propenethione
• 英文别名: 2-(4-bromophenyl)-1,3-dimorpholin-4-ylprop-2-ene-1-thione
• CAS: 159298-76-7
• 化学式: C₁₇H₂₁BrN₂O₂S
• 分子量: 397.336
• InChiKey: FDYVTBUBONFJTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  24.94
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-2-(4-Bromo-phenyl)-1,3-di-morpholin-4-yl-propenethione 在 双氧水 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 1.25h， 生成 AWD 140-190
  参考文献：
  名称：

  Synthesis, Anticonvulsant Activity, and Structure−Activity Relationships of Sodium Channel Blocking 3-Aminopyrroles

  摘要：

  Starting from the corresponding acetophenone and glycine derivatives, a series of new 3-aminopyrroles was synthesized in few steps. Using this procedure with hydrazine and hydroxylamine instead of the glycinates provides access to S-aminopyrazoles and 5-amino-1,2-oxazoles. The various derivatives were tested for anticonvulsant activity in a variety of test models. Several compounds exhibit considerable activity with a remarkable lack of neurotoxicity. 4-(4-Bromophenyl)-3-morpholinopyrrole-2-carboxylic acid methyl ester, 3, proved to be the most active compound. It was protective in the maximal electroshock seizure (MES) test in rats with an oral ED50 of 2.5 mg/kg with no neurotoxicity noted at doses up to 500 mg/kg. Compound 3 blocks sodium channels in a frequency-dependent manner. The essential structural features which could be responsible for an interaction with an active site of the voltage-dependent sodium channel are established within a suggested pharmacophore model.

  DOI：

  10.1021/jm970327j
• 作为产物：
  描述：

  吗啉 、 2-(4-溴苯基)-1-(4-吗啉)乙烷硫酮 、 原甲酸三乙酯 反应 4.0h， 以78%的产率得到(Z)-2-(4-Bromo-phenyl)-1,3-di-morpholin-4-yl-propenethione
  参考文献：
  名称：

  Efficient Synthesis of 3-Aminothioacrylamides by Iminoformylation of Thioacetamides

  摘要：

  将取代的硫代乙酰胺 1 与三吗啉甲烷或原甲酸三乙酯和仲胺的混合物一起加热，可以得到高产率的合成用途广泛的 3-氨基硫代丙烯酰胺 4。

  DOI：

  10.1055/s-1994-25545

文献信息

• Synthesis, Anticonvulsant Activity, and Structure−Activity Relationships of Sodium Channel Blocking 3-Aminopyrroles
  作者：Klaus Unverferth、Jürgen Engel、Norbert Höfgen、Angelika Rostock、Ralf Günther、Hans-Joachim Lankau、Manfred Menzer、Andreas Rolfs、Jürgen Liebscher、Birgit Müller、Hans-Jörg Hofmann

  DOI：10.1021/jm970327j

  日期：1998.1.1

  Starting from the corresponding acetophenone and glycine derivatives, a series of new 3-aminopyrroles was synthesized in few steps. Using this procedure with hydrazine and hydroxylamine instead of the glycinates provides access to S-aminopyrazoles and 5-amino-1,2-oxazoles. The various derivatives were tested for anticonvulsant activity in a variety of test models. Several compounds exhibit considerable activity with a remarkable lack of neurotoxicity. 4-(4-Bromophenyl)-3-morpholinopyrrole-2-carboxylic acid methyl ester, 3, proved to be the most active compound. It was protective in the maximal electroshock seizure (MES) test in rats with an oral ED50 of 2.5 mg/kg with no neurotoxicity noted at doses up to 500 mg/kg. Compound 3 blocks sodium channels in a frequency-dependent manner. The essential structural features which could be responsible for an interaction with an active site of the voltage-dependent sodium channel are established within a suggested pharmacophore model.
• Efficient Synthesis of 3-Aminothioacrylamides by Iminoformylation of Thioacetamides
  作者：Andreas Rolfs、Jürgen Liebscher

  DOI：10.1055/s-1994-25545

  日期：——

  Heating substituted thioacetamides 1 with either trismorpholinomethane or with a mixture of triethyl orthoformate and a secondary amine gives high yields of synthetically versatile 3-aminothioacryl-amides 4.

  将取代的硫代乙酰胺 1 与三吗啉甲烷或原甲酸三乙酯和仲胺的混合物一起加热，可以得到高产率的合成用途广泛的 3-氨基硫代丙烯酰胺 4。