1-[(4-溴-2-氟苯基)甲基]-7-氯吲哚-2,3-二酮 | 89159-25-1

• 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
• 中文名称: 1-[(4-溴-2-氟苯基)甲基]-7-氯吲哚-2,3-二酮
• 英文名称: 1-(4-bromo-2-fluorobenzyl)-7-chloro-indoline-2,3-dione
• 英文别名: 1-[(4-Bromo-2-fluorophenyl)methyl]-7-chloro-1H-indole-2,3-dione；1-[(4-bromo-2-fluorophenyl)methyl]-7-chloroindole-2,3-dione
• CAS: 89159-25-1
• 化学式: C₁₅H₈BrClFNO₂
• 分子量: 368.589
• InChiKey: DHTZABNLHNWPEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-N,N,N-trimethyl-(1-phenylethyl)ammonium hydroxide 、 1-[(4-溴-2-氟苯基)甲基]-7-氯吲哚-2,3-二酮 生成 1'-(4-bromo-2-fluorobenzyl)-7'-chloro-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  7-氯靛红 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 1-[(4-溴-2-氟苯基)甲基]-7-氯吲哚-2,3-二酮
  参考文献：
  名称：

  Discovery of the First Highly M5-Preferring Muscarinic Acetylcholine Receptor Ligand, an M5 Positive Allosteric Modulator Derived from a Series of 5-Trifluoromethoxy N-Benzyl Isatins

  摘要：

  This report describes the discovery and initial characterization of the first positive allosteric modulator of muscarinic acetylcholine receptor subtype 5 (mAChR5 or M5). Functional HTS, identified VU0119498, which displayed micromolar potencies for potentiation of acetylcholine at M1, M3, and M5 receptors in cell-based Ca2+ mobilization assays. Subsequent optimization led to the discovery of VU0238429, which possessed an EC50 of approximately 1.16 mu M at M5 with >30-fold selectivity versus M1 and M3, with no M2 or M4 potentiator activity.

  DOI：

  10.1021/jm900286j

文献信息

• Aldose reductase inhibition by spiro indoline derivatives
  申请人：Imperial Chemical Industries PLC

  公开号：US04581366A1

  公开（公告）日：1986-04-08

  The invention concerns 1'-(4-bromo-2-fluorobenzyl)-7'-chloro-spiro[imidazolidine-4,3'-indoline]-2 ,2',5-trione in racemic or dextrorotatory form; pharmaceutical compositions thereof for use in the treatment or prophylaxis of certain complications of diabetes; and processes for its manufacture.

  该发明涉及1'-(4-溴-2-氟苯基)-7'-氯-螺[咪唑啉-4,3'-吲哚啉]-2,2',5-三酮的外消旋或右旋形式；以及用于治疗或预防糖尿病某些并发症的制药组合物；以及其制造方法。
• Process for racemizing certain spiro compounds
  申请人：Imperial Chemical Industries PLC

  公开号：US04567278A1

  公开（公告）日：1986-01-28

  The invention concerns a novel process for the racemisation of unwanted enantiomeric forms of 1'-substituted spiro[imidazolidine-4,3'-indoline]-2,2',5-triones and 1'-substituted spiro[pyrrolidine-3,3'-indoline]-2,2',5-triones which comprises heating an unwanted enantiomeric form (or a mixture containing an excess of one enantiomer over the other) alone or, more conveniently, in the presence of a solvent or diluent at a temperature in the range 80.degree. to 280.degree. C.

  本发明涉及一种新的过程，用于消旋化1'-取代的螺[咪唑啉-4，3'-茚啉]-2,2'，5-三酮和1'-取代的螺[吡咯烷-3，3'-茚啉]-2,2'，5-三酮的非所需对映异构体，包括在80°C到280°C的温度范围内加热非所需对映异构体（或含有一种对映体超过另一种对映体的混合物），单独或更方便地，在溶剂或稀释剂的存在下。
• Process for resolving certain spiro compounds
  申请人：Imperial Chemical Industries PLC

  公开号：US04611062A1

  公开（公告）日：1986-09-09

  The invention concerns a novel process for the racemization of unwanted enantiomeric forms of 1'-substituted spiro[imidazolidine-4,3'-indoline]-2,2',5-triones and 1'-substituted spiro[pyrrolidine-3,3'-indoline]-2,2',5-triones which comprises heating an unwanted enantiomeric form (or a mixture containing an excess of one enantiomer over the other) alone or, more conveniently, in the presence of a solvent or diluent at a temperature in the range 80.degree. to 280.degree. C.

  本发明涉及一种新型的过程，用于消旋不需要的对映异构体形式的1'-取代螺[咪唑啉-4,3'-茚]-2,2',5-三酮和1'-取代螺[吡咯烷-3,3'-茚]-2,2',5-三酮的消旋化，其中包括将不需要的对映异构体形式（或含有一种对映异构体优于另一种的混合物）单独或更方便地在溶剂或稀释剂的存在下加热到80℃至280℃的温度范围内。
• Indoline derivatives
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0125090A2

  公开（公告）日：1984-11-14

  The invention concerns 1'-(4-bromo -2-fluorobenryl)-7'-chloro-spiro [imidazolidine -4,3'- indoline] -2,2',5- trione in racemic or dextrorotatory form; pharmaceutical compositions thereof for use in the treatment or prophylaxis of certain complications of diabetes;and processes for its manufacture.

  本发明涉及外消旋或右旋形式的 1'-(4-溴-2-氟苯乙烯基)-7'-氯-螺[咪唑啉-4,3'-吲哚啉]-2,2',5-三酮；用于治疗或预防糖尿病某些并发症的药物组合物；及其生产工艺。
• Cyclic amides
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0168181A1

  公开（公告）日：1986-01-15

  The invention concerns the novel cyclic amide 1'-(4-bromo-2-fluorobenzyl)-7'-chloro-spiro[pyrrolidine-3,3'- indoline]-2.2',5-trione in laevorotatory optically active form, its salts, pharmaceutical compositions and methods of manufacture. The novel cyclic amide is of value in the treatment or prophylaxis of various complications of diabetes and galactosemia.

  本发明涉及新型环酰胺 1'-(4-溴-2-氟苄基)-7'-氯-螺[吡咯烷-3,3'-吲哚啉]-2.2',5-三酮，其光学活性形式为月桂酸性，涉及其盐类、药物组合物和制造方法。这种新型环酰胺具有治疗或预防糖尿病和半乳糖血症各种并发症的价值。