ethyl (1S,12bR)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-1-(2'-hydroxyimino)propionate | 105221-74-7

• 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 (1S,12bR)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-1-(2'-hydroxyimino)propionate
• CAS: 105221-74-7
• 化学式: C₂₂H₂₉N₃O₃
• 分子量: 383.491
• InChiKey: MFYCQYKHMWOTBY-UNMCSNQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  77.92
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl (1S,12bR)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-1-(2'-hydroxyimino)propionate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以75%的产率得到长春西汀杂质1
  参考文献：
  名称：

  Synthesis and Evaluation of 2′-Hydroxyethyl trans-Apovincaminate Derivatives as Antioxidant and Cognitive Enhancer Agents

  摘要：

  A series of trans-2'-hydroxyethyl and 2'-acyloxyethyl apovincaminates 4b-f and 7b-f has been synthesized and evaluated for their antioxidant and antiamnesic effects. The new esters were prepared from 4a and 7a ethyl esters or from the corresponding carboxylic acid sodium salt. For starting materials 11a,b, a new stereoselective trans-reduction was elaborated. From the combined results of the data obtained from in vitro and in vivo tests and examination of the metabolism, (3R,16S)-2'-hydroxyethyl apovincaminate (7b, RGH-10885) was identified as the most promising compound, owing to its potent neuroprotective and antiamnesic activities. The in vivo effectiveness of selected compounds on the cognitive functions was studied in a one-trial passive avoidance task and a water-labyrinth test.

  DOI：

  10.1021/jm070618k
• 作为产物：
  描述：

  (1S,12bR)-1-(2',2'-diethoxycarbonylethyl)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a] quinolizine 在 氢氧化钾 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以69.6%的产率得到ethyl (1S,12bR)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-1-(2'-hydroxyimino)propionate
  参考文献：
  名称：

  Synthesis and Evaluation of 2′-Hydroxyethyl trans-Apovincaminate Derivatives as Antioxidant and Cognitive Enhancer Agents

  摘要：

  A series of trans-2'-hydroxyethyl and 2'-acyloxyethyl apovincaminates 4b-f and 7b-f has been synthesized and evaluated for their antioxidant and antiamnesic effects. The new esters were prepared from 4a and 7a ethyl esters or from the corresponding carboxylic acid sodium salt. For starting materials 11a,b, a new stereoselective trans-reduction was elaborated. From the combined results of the data obtained from in vitro and in vivo tests and examination of the metabolism, (3R,16S)-2'-hydroxyethyl apovincaminate (7b, RGH-10885) was identified as the most promising compound, owing to its potent neuroprotective and antiamnesic activities. The in vivo effectiveness of selected compounds on the cognitive functions was studied in a one-trial passive avoidance task and a water-labyrinth test.

  DOI：

  10.1021/jm070618k