Methyl (E)4.6-dichloro3-(2-oxo-1-phenyl-pyrrolidin-3-ylidenemethyl)-1H-indole-2-carboxylate | 166974-21-6

• 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: Methyl (E)4.6-dichloro3-(2-oxo-1-phenyl-pyrrolidin-3-ylidenemethyl)-1H-indole-2-carboxylate
• 英文别名: Methyl (E)-4,6-dichloro-3-(2-oxo-1-phenyl-pyrrolidin-3-ylidenemethyl)-1H-indole-2-carboxylate；methyl 4,6-dichloro-3-[(E)-(2-oxo-1-phenylpyrrolidin-3-ylidene)methyl]-1H-indole-2-carboxylate
• CAS: 166974-21-6
• 化学式: C₂₁H₁₆Cl₂N₂O₃
• 分子量: 415.276
• InChiKey: UZESEVMKKKZACS-FMIVXFBMSA-N

物化性质

• 沸点：
  615.0±55.0 °C(Predicted)
• 密度：
  1.470±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl (E)4.6-dichloro3-(2-oxo-1-phenyl-pyrrolidin-3-ylidenemethyl)-1H-indole-2-carboxylate 在 盐酸 、 lithium hydroxide monohydrate 作用下， 以 乙醇 为溶剂， 生成 4,6-二氯-3-[(E)-(2-氧代-1-苯基-3-吡咯烷基亚基)甲基]-1H-吲哚-2-羧酸
  参考文献：
  名称：

  Indole derivatives

  摘要：

  这项发明涉及以下式的化合物##STR1##或其盐，或代谢易降解的酯，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.2 R.sub.2或COR.sub.2中选择的基团，其中R.sub.2代表羟基、甲氧基、氨基、烷基氨基或二烷基氨基；m为零或整数1或2；R.sub.1代表环烷基、桥环烷基、杂环烷基、桥接杂环烷基或可选择取代的苯基或融合的双环碳环基团；A代表C.sub.1-4烷基链或链(CH.sub.2).sub.p Y(CH.sub.2).sub.q，其中Y为O、S(O)n或NR.sub.3，这些链可以被一个或两个选自C.sub.1-6烷基（可选择地取代为羟基、氨基、烷基氨基或二烷基氨基）的基团取代，或这些链可以被基团.dbd.O取代；R.sub.3代表氢、烷基或氮保护基；n为零或整数1到2；p为零或整数1到3；q为零或整数1到3，但p+q的总和为1、2或3，这些化合物是兴奋性氨基酸的拮抗剂，用于制备的方法以及在医学中的其他用途。

  公开号：

  US05760059A1
• 作为产物：
  描述：

  4,6-dichloro-3-formyl-1-(2-trimethylsilanylethoxymethyl)-indole-2-carboxylic acid ethyl ester 在 盐酸 、 叔丁基锂 、 三甲基硅烷化重氮甲烷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 13.67h， 生成 Methyl (E)4.6-dichloro3-(2-oxo-1-phenyl-pyrrolidin-3-ylidenemethyl)-1H-indole-2-carboxylate
  参考文献：
  名称：

  Unusual synthesis of new glycine antagonists via sequential aldol condensation-lactonization-elimination reaction

  摘要：

  Compounds 2 and 3 were designed in older to probe the North-East region of the strichnine-insensitive glycine binding site of the NMDA receptor. The two products were obtained readily by a tandem aldol condensation-lactonization-elimination step which affords the desired E isomer with complete regioselection. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00284-4

文献信息

• Indole derivatives as NMDA antagonists
  申请人：Glaxo Wellcome SpA

  公开号：US05962496A1

  公开（公告）日：1999-10-05

  This invention relates to compounds of formula ##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.2 or COR.sub.2 wherein R.sub.2 represents hydroxy, methoxy, amino, alkylamino, or dialkylamino; m is zero or an integer 1 or 2; R.sub.1 represents a cycloalkyl, bridged cycloalkyl, heteroaryl, bridged heterocyclic or optionally substituted phenyl or fused bicyclic carbocylic group; A represents a C.sub.1-4 alkylene chain or the chain (CH.sub.2).sub.p Y(CH.sub.2).sub.q wherein Y is O, S(O)n or NR.sub.3 and which chains may be substituted by one or two groups selected from C.sub.1-6 alkyl optionally substituted by hydroxy, amino, alkylamino or dialkylamino, or which chains may be substituted by the group=O; R.sub.3 represents hydrogen, alkyl or a nitrogen protecting group; n is zero or an integer from 1 to 2; p is zero or an integer from 1 to 3; q is zero or an integer from 1 to 3 with the proviso that the sum of p+q is 1, 2 or 3, which are antagonists of excitatory amino acids, to processes for the preparation and to other use in medicine.

  本发明涉及公式##STR1##或其盐或代谢易变酯，其中R代表选自卤素，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.2或COR.sub.2的基团，其中R.sub.2代表羟基，甲氧基，氨基，烷基氨基或二烷基氨基；m为零或整数1或2；R.sub.1代表环烷基，桥联环烷基，杂环基，桥联杂环基或可选取代苯基或融合的双环碳环基；A代表C.sub.1-4烷基链或链(CH.sub.2).sub.p Y(CH.sub.2).sub.q，其中Y为O，S(O)n或NR.sub.3，这些链可以被选自C.sub.1-6烷基的一或两个取代基取代，这些烷基可以被羟基，氨基，烷基氨基或二烷基氨基取代，或这些链可以被基团=O取代；R.sub.3代表氢，烷基或氮保护基；n为零或整数1到2；p为零或整数1到3；q为零或整数1到3，但p + q的总和为1、2或3，这些化合物是兴奋性氨基酸的拮抗剂，可用于医学制剂的制备和其他用途。
• Bioorganic and Medicinal Chemistry Letters 1998, 8, 1689-1692
  作者：

  DOI：——

  日期：——
• Unusual synthesis of new glycine antagonists via sequential aldol condensation-lactonization-elimination reaction
  作者：Simone A. Giacobbe、Davide Baraldi、Romano Di Fabio

  DOI：10.1016/s0960-894x(98)00284-4

  日期：1998.7

  Compounds 2 and 3 were designed in older to probe the North-East region of the strichnine-insensitive glycine binding site of the NMDA receptor. The two products were obtained readily by a tandem aldol condensation-lactonization-elimination step which affords the desired E isomer with complete regioselection. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Indole derivatives
  申请人：Glaxo Wellcome SpA

  公开号：US05760059A1

  公开（公告）日：1998-06-02

  This invention relates to compounds of formula ##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.2 or COR.sub.2 wherein R.sub.2 represents hydroxy, methoxy, amino, alkylamino, or dialkylamino; m is zero or an integer 1 or 2; R.sub.1 represents a cycloalkyl, bridged cycloalkyl, heteroaryl, bridged heterocyclic or optionally substituted phenyl or fused bicyclic carbocylic group; A represents a C.sub.1-4 alkylene chain or the chain (CH.sub.2).sub.p Y(CH.sub.2).sub.q wherein Y is O, S(O)n or NR.sub.3 and which chains may be substituted by one or two groups selected from C.sub.1-6 alkyl optionally substituted by hydroxy, amino, alkylamino or dialkylamino, or which chains may be substituted by the group .dbd.O; R.sub.3 represents hydrogen, alkyl or a nitrogen protecting group; n is zero or an integer from 1 to 2; p is zero or an integer from 1 to 3; q is zero or an integer from 1 to 3 with the proviso that the sum of p+q is 1, 2 or 3, which are antagonists of excitatory amino acids, to processes for the preparation and to other use in medicine.

  这项发明涉及以下式的化合物##STR1##或其盐，或代谢易降解的酯，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.2 R.sub.2或COR.sub.2中选择的基团，其中R.sub.2代表羟基、甲氧基、氨基、烷基氨基或二烷基氨基；m为零或整数1或2；R.sub.1代表环烷基、桥环烷基、杂环烷基、桥接杂环烷基或可选择取代的苯基或融合的双环碳环基团；A代表C.sub.1-4烷基链或链(CH.sub.2).sub.p Y(CH.sub.2).sub.q，其中Y为O、S(O)n或NR.sub.3，这些链可以被一个或两个选自C.sub.1-6烷基（可选择地取代为羟基、氨基、烷基氨基或二烷基氨基）的基团取代，或这些链可以被基团.dbd.O取代；R.sub.3代表氢、烷基或氮保护基；n为零或整数1到2；p为零或整数1到3；q为零或整数1到3，但p+q的总和为1、2或3，这些化合物是兴奋性氨基酸的拮抗剂，用于制备的方法以及在医学中的其他用途。