(Z)-1-benzenesulfonyl-3-(2-carboxy-2-chlorovinyl)-4,6-dichloroindole-2-carboxylic acid ethyl ester | 159054-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (Z)-1-benzenesulfonyl-3-(2-carboxy-2-chlorovinyl)-4,6-dichloroindole-2-carboxylic acid ethyl ester
• CAS: 159054-22-5
• 化学式: C₂₀H₁₄Cl₃NO₆S
• 分子量: 502.759
• InChiKey: WTSYUYDHPODEBF-GDNBJRDFSA-N

物化性质

• 沸点：
  699.3±65.0 °C(predicted)
• 密度：
  1.54±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  102.67
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (Z)-1-benzenesulfonyl-3-(2-carboxy-2-chlorovinyl)-4,6-dichloroindole-2-carboxylic acid ethyl ester 在 lithium hydroxide 、 2,2'-二硫二吡啶 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 38.5h， 生成 4,6-Dichloro-3-((Z)-2-chloro-2-phenylcarbamoyl-vinyl)-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Substituted Indole-2-carboxylates as Potent Antagonists of the Glycine Binding Site Associated with the NMDA Receptor

  摘要：

  A novel series of indole-2-carboxylate analogues of GV 150526 (1) in which the propenoic double bond was substituted with different "probes" or replaced by a isosteric cyclopropyl moiety were synthesized and evaluated for their affinity profile in order to obtain further information on the pharmacophoric model of the glycine binding site associated to the NMDA receptor.

  DOI：

  10.1002/(sici)1521-4184(19998)332:8<271::aid-ardp271>3.0.co;2-x
• 作为产物：
  描述：

  1-Benzenesulfonyl-4,6-dichloro-3-formyl-1H-indole-2-carboxylic acid ethyl ester 在 甲酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (Z)-1-benzenesulfonyl-3-(2-carboxy-2-chlorovinyl)-4,6-dichloroindole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  New Synthesis of Substituted 2-Carboxyindole Derivatives: Versatile Introduction of a Carbamoylethynyl Moiety at the C-3 Position

  摘要：

  A novel series of 3-carbamoylethynyl-2-carboxyindoles, antagonists acting at the strychnine-insensitive glycine binding site associated with the NMDA receptor, has been synthesised. This new versatile approach involves the introduction of a 2-chloroethenyl moiety in position C-3 with subsequent derivatisation of the terminal carboxyl group, followed by an unusual elimination of HCl to afford the ethynyl functionality. This novel series of glycine antagonists was evaluated in terms of in vitro affinity at the glycine bindings site and the most potent compound was tested in vivo in the NMDA-induced convulsions model in mice.

  DOI：

  10.1002/(sici)1521-4184(19993)332:2<55::aid-ardp55>3.0.co;2-z