[(E)-2-(4-Chloro-phenyl)-3-morpholin-4-yl-3-thioxo-propenylamino]-acetic acid methyl ester | 98236-50-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(E)-2-(4-Chloro-phenyl)-3-morpholin-4-yl-3-thioxo-propenylamino]-acetic acid methyl ester
• 英文别名: methyl 2-[[2-(4-chlorophenyl)-3-morpholin-4-yl-3-sulfanylideneprop-1-enyl]amino]acetate
• CAS: 98236-50-1
• 化学式: C₁₆H₁₉ClN₂O₃S
• 分子量: 354.857
• InChiKey: OJKFEPYCTHBGDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  50.8
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [(E)-2-(4-Chloro-phenyl)-3-morpholin-4-yl-3-thioxo-propenylamino]-acetic acid methyl ester 在 氢氧化钾 、 碘 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 4-(4-chlorophenyl)-3-morpholinopyrrole
  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：

  甘胺酸甲酯 、 2-(4-chlorophenyl)-1,3-di(morpholin-4-yl)propenethione 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 [(E)-2-(4-Chloro-phenyl)-3-morpholin-4-yl-3-thioxo-propenylamino]-acetic acid methyl ester
  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

文献信息

• Electrochemical Synthesis of 5-Amino-1,2-thiazolium Salts and their ring transformation to 3-aminopyrroles
  作者：Andreas Rolfs、J�rgen Liebscher、Holger Brosig

  DOI：10.1002/prac.19953370163

  日期：——
• Synthesis of esters of substituted 3-aminopyrrole-2-carboxylic acids from thioacrylamides and glycine esters
  作者：A. P. Knoll、J. Liebscher

  DOI：10.1007/bf00506065

  日期：1985.5
• 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.