AWD 140-076 | 98236-55-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: AWD 140-076
• 英文别名: Methyl 4-(4-chlorophenyl)-3-(4-morpholinyl)-1H-pyrrole-2-carboxylate；methyl 4-(4-chlorophenyl)-3-morpholin-4-yl-1H-pyrrole-2-carboxylate
• CAS: 98236-55-6
• 化学式: C₁₆H₁₇ClN₂O₃
• 分子量: 320.776
• InChiKey: JABTZFPCSIXMOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  AWD 140-076 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以95%的产率得到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：

  [(E)-2-(4-Chloro-phenyl)-3-morpholin-4-yl-3-thioxo-propenylamino]-acetic acid methyl ester 在 碘 、 三乙胺 作用下， 以 乙醇 为溶剂， 生成 AWD 140-076
  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

• Langner; Melzig; Kempa, Pharmazie, 1995, vol. 50, # 2, p. 130 - 138
  作者：Langner、Melzig、Kempa、Krause

  DOI：——

  日期：——
• 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
• KNOLL, A. P.;LIBSHER, YU., XIMIYA GETEROTSIKL. SOEDIN., 1985, N 5, 628-630
  作者：KNOLL, A. P.、LIBSHER, YU.

  DOI：——

  日期：——
• Rolfs, Andreas; Liebscher, Juergen, Angewandte Chemie, 1993, vol. 105, # 5, p. 797 - 799
  作者：Rolfs, Andreas、Liebscher, Juergen

  DOI：——

  日期：——

表征谱图