(-)-trans-Apovincaminic acid 2-hydroxyethyl ester | 192813-34-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - Eburnan型生物碱
• 英文名称: (-)-trans-Apovincaminic acid 2-hydroxyethyl ester
• 英文别名: 2-hydroxyethyl (15S,19R)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylate
• CAS: 192813-34-6
• 化学式: C₂₂H₂₆N₂O₃
• 分子量: 366.46
• InChiKey: WBEVCQPAHIHTRP-UNMCSNQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-trans-Apovincaminic acid 2-hydroxyethyl ester 、 4-氯苯甲酰氯 在 三乙胺 作用下， 以 氯苯 为溶剂， 反应 0.5h， 生成 2-(4-chlorobenzoyl)oxyethyl (15S,19R)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylate
  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：

  乙二醇 、 长春西汀杂质1 在 potassium tert-butylate 作用下， 反应 4.0h， 以91%的产率得到(-)-trans-Apovincaminic acid 2-hydroxyethyl ester
  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

文献信息

• Synthesis and Evaluation of 2′-Hydroxyethyl <i>trans-</i>Apovincaminate Derivatives as Antioxidant and Cognitive Enhancer Agents
  作者：András Nemes、László Czibula、Csaba Szántay, Jr.、Anikó Gere、Béla Kiss、Judit Laszy、István Gyertyán、Zsolt Szombathelyi、Csaba Szántay

  DOI：10.1021/jm070618k

  日期：2008.2.1

  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.