Ethyl 3-(2'-(1-Adamantylcarbamoyl)-ethynyl)-4,6-dichloroindole-2-carboxylate | 159054-10-1

• 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: Ethyl 3-(2'-(1-Adamantylcarbamoyl)-ethynyl)-4,6-dichloroindole-2-carboxylate
• 英文别名: ethyl 3-[3-(1-adamantylamino)-3-oxoprop-1-ynyl]-4,6-dichloro-1H-indole-2-carboxylate
• CAS: 159054-10-1
• 化学式: C₂₄H₂₄Cl₂N₂O₃
• 分子量: 459.372
• InChiKey: HJCWCXJBNVPLCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 3-(2'-(1-Adamantylcarbamoyl)-ethynyl)-4,6-dichloroindole-2-carboxylate 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 3-(2'-(1-Adamantylcarbamoyl)-ethynyl)-4,6-dichloroindole-2-carboxylic acid sodium salt
  参考文献：
  名称：

  Indole derivatives

  摘要：

  该发明涉及式（I）的化合物。##STR1##或其盐或代谢易变酯，其中R.sub.1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.3或COR.sub.3中选择的基团，其中R.sub.3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; X代表键或C.sub.1-4烷基链; R.sub.2代表桥式环烷基或桥式杂环基; 这些化合物是兴奋性氨基酸拮抗剂，用于制备这些化合物的方法以及在医学上的应用。

  公开号：

  US05686461A1
• 作为产物：
  描述：

  1-benzenesulfonyl-3-(2-carboxy-2-chlorovinyl)-4,6-dichloroindole-2-carboxylic acid ethyl ester 在 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 39.5h， 生成 Ethyl 3-(2'-(1-Adamantylcarbamoyl)-ethynyl)-4,6-dichloroindole-2-carboxylate
  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

文献信息

• Indole derivatives
  申请人：Glaxo Wellcome S.p.A.

  公开号：US05686461A1

  公开（公告）日：1997-11-11

  The invention relates to compounds of formula (I). ##STR1## or a salt, or metabolically labile ester thereof wherein R.sub.1 represents a group selected from halogen, alkyl, alkoxy, amino, alkylamino, dialkylamino, hydroxy, trifluoromethyl, trifluoromethoxy, nitro, cyano, SO.sub.2 R.sub.3 or COR.sub.3 wherein R.sub.3 represents hydroxy, methoxy, or amino; m is zero or an integer 1 or 2; A represents an ethynyl group or an optionally substituted ethenyl group; X represents a bond or a C.sub.1-4 alkylene chain; R.sub.2 represents a bridged cycloalkyl or bridged heterocyclic group; which are antagonists of excitatory amino acids, to processes for their preparation and to their use in medicine.

  本发明涉及式(I)的化合物。其中，R1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、SO2R3或COR3中选择的基团，其中R3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；X代表键或C1-4烷基链；R2代表桥环烷基或桥环杂环基团。这些化合物是兴奋性氨基酸的拮抗剂，本发明还涉及其制备方法及在医药上的应用。
• US5686461A
  申请人：——

  公开号：US5686461A

  公开（公告）日：1997-11-11
• New Synthesis of Substituted 2-Carboxyindole Derivatives: Versatile Introduction of a Carbamoylethynyl Moiety at the C-3 Position
  作者：Cheryl T. Hewkin、Romano Di Fabio、Nadia Conti、Alfredo Cugola、Paola Gastaldi、Fabrizio Micheli、Anna M. Quaglia

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

  日期：1999.3

  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.