E-1-(2-(trimethylsilyl)ethoxymethyl)-3-(2-phenylcarbamoylvinyl)-4,6-dichloroindole-2-carboxylic acid ethyl ester | 153436-02-3

• 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: E-1-(2-(trimethylsilyl)ethoxymethyl)-3-(2-phenylcarbamoylvinyl)-4,6-dichloroindole-2-carboxylic acid ethyl ester
• 英文别名: (E)-Ethyl 3-[2-(phenylcarbamoyl)ethenyl]-1-(2-trimethylsilylethoxymethyl)-4,6-dichloroindole-2-carboxylate；ethyl 3-[(E)-3-anilino-3-oxoprop-1-enyl]-4,6-dichloro-1-(2-trimethylsilylethoxymethyl)indole-2-carboxylate
• CAS: 153436-02-3
• 化学式: C₂₆H₃₀Cl₂N₂O₄Si
• 分子量: 533.527
• InChiKey: WXGIABJQLSFKHO-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.09
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  E-1-(2-(trimethylsilyl)ethoxymethyl)-3-(2-phenylcarbamoylvinyl)-4,6-dichloroindole-2-carboxylic acid ethyl ester 在 palladium diacetate 盐酸 、 lithium hydroxide 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 反应 9.0h， 生成 E-3-(2-phenylcarbamoylcyclopropyl)-4,6-dichloroindole-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：

  2-(三甲基硅烷基)乙氧甲基氯 、 GV150526 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以80%的产率得到E-1-(2-(trimethylsilyl)ethoxymethyl)-3-(2-phenylcarbamoylvinyl)-4,6-dichloroindole-2-carboxylic acid ethyl ester
  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

文献信息

• Indole derivatives and pharmaceutical use thereof
  申请人：Glaxo S.p.A.

  公开号：US05374648A1

  公开（公告）日：1994-12-20

  The invention relates to compounds of formula (I). ##STR1## or a salt, or metabolically labile ester thereof wherein R represents a group selected from halogen, alkyl, alkoxy, amino, alkylamino, dialkylamino, hydroxy, trifluoromethyl, trifluoromethoxy, nitro, cyano, SO.sub.2 R.sub.1 or COR.sub.1 wherein R.sub.1 represents hydroxy, methoxy, or amino; m is zero or an integer 1 or 2; A represents an ethynyl group or an optionally substituted ethenyl, or cyclopropyl group or a substituted ethenyl group; X represents --O-- or NH; R.sub.2 represents an aryl group and when X represents an oxygen atom R.sub.2 may also represent a hydrogen atom or an alkyl group; which are antagonists of excitatory amino acids, to processes for their preparation and to their use in medicine.

  本发明涉及公式（I）的化合物。 ##STR1## 或其盐或代谢易降解酯，其中R代表从卤素，烷基，烷氧基，氨基，烷基氨基，二烷基氨基，羟基，三氟甲基，三氟甲氧基，硝基，氰基，SO.sub.2R.sub.1或COR.sub.1中选择的基团，其中R.sub.1代表羟基，甲氧基或氨基；m为零或整数1或2；A代表乙炔基或可选取代的乙烯基，环丙基或取代的乙烯基；X代表--O--或NH；R.sub.2代表芳基，当X代表氧原子时，R.sub.2也可以代表氢原子或烷基；它们是兴奋性氨基酸的拮抗剂，本发明还涉及其制备方法及其在医学上的应用。
• Substituted Indole-2-carboxylates as Potent Antagonists of the Glycine Binding Site Associated with the NMDA Receptor
  作者：Fabrizio Micheli、Romano Di Fabio、Davide Baraldi、Nadia Conti、Alfredo Cugola、Paola Gastaldi、Simone Giacobbe、Carla Marchioro、Manolo Mugnaini、Luciana Rossi、Angelo Pecunioso、Giorgio Pentassuglia

  DOI：10.1002/(sici)1521-4184(19998)332:8<271::aid-ardp271>3.0.co;2-x

  日期：1999.8

  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.