(2-oxo-4-phenyl-1-pyrrolidinyl)acetic acid carboethoxymethyl ester | 208844-53-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2-oxo-4-phenyl-1-pyrrolidinyl)acetic acid carboethoxymethyl ester
• 英文别名: (2-ethoxy-2-oxoethyl) 2-(2-oxo-4-phenylpyrrolidin-1-yl)acetate
• CAS: 208844-53-5
• 化学式: C₁₆H₁₉NO₅
• 分子量: 305.331
• InChiKey: IGKANDGMTYVVIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  476.9±45.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-oxo-4-phenyl-1-pyrrolidinyl)acetic acid carboethoxymethyl ester 在 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 N-butyl-N~2~-[(2-oxo-4-phenylpyrrolidin-1-yl)acetyl]glycinamide
  参考文献：
  名称：

  Shipov; Kramarova; Kalashnikova, Russian Journal of General Chemistry, 1997, vol. 67, # 11, p. 1736 - 1741

  摘要：

  DOI：
• 作为产物：
  描述：

  4-苯基-1-(三甲基甲硅烷基)-2-吡咯烷酮 、 ethoxycarbonylmethyl chloroacetate 反应 1.0h， 以30%的产率得到(2-oxo-4-phenyl-1-pyrrolidinyl)acetic acid carboethoxymethyl ester
  参考文献：
  名称：

  Shipov; Kramarova; Kalashnikova, Russian Journal of General Chemistry, 1997, vol. 67, # 11, p. 1736 - 1741

  摘要：

  DOI：

文献信息

• A Novel Phenylpyrrolidine Derivative: Synthesis and Effect on Cognitive Functions in Rats with Experimental Ishemic Stroke
  作者：Denis A. Borozdenko、Aiarpi A. Ezdoglian、Tatiana A. Shmigol、Darya I. Gonchar、Dmitri N. Lyakhmun、Dmitri V. Tarasenko、Yaroslav V. Golubev、Elvira A. Cherkashova、Daria D. Namestnikova、Ilya L. Gubskiy、Alexey A. Lagunin、Leonid V. Gubsky、Vladimir P. Chekhonin、Sophia S. Borisevich、Maxim A. Gureev、Anastasia D. Shagina、Nina M. Kiseleva、Vadim V. Negrebetsky、Yuri I. Baukov

  DOI：10.3390/molecules26206124

  日期：——

  We performed an in silico, in vitro, and in vivo assessment of a potassium 2-[2-(2-oxo-4-phenylpyrrolidin-1-yl) acetamido]ethanesulfonate (compound 1) as a potential prodrug for cognitive function improvement in ischemic brain injury. Using in silico methods, we predicted the pharmacological efficacy and possible safety in rat models. In addition, in silico data showed neuroprotective features of compound 1, which were further supported by in vitro experiments in a glutamate excitotoxicity-induced model in newborn rat cortical neuron cultures. Next, we checked whether compound 1 is capable of crossing the blood–brain barrier in intact and ischemic animals. Compound 1 improved animal behavior both in intact and ischemic rats and, even though the concentration in intact brains was low, we still observed a significant anxiety reduction and activity escalation. We used molecular docking and molecular dynamics to support our hypothesis that compound 1 could affect the AMPA receptor function. In a rat model of acute focal cerebral ischemia, we studied the effects of compound 1 on the behavior and neurological deficit. An in vivo experiment demonstrated that compound 1 significantly reduced the neurological deficit and improved neurological symptom regression, exploratory behavior, and anxiety. Thus, here, for the first time, we show that compound 1 can be considered as an agent for restoring cognitive functions.

  我们对一种潜在的前药——2-[2-(2-氧代-4-苯基吡咯啉-1-基)乙酰胺基]乙磺酸钾（化合物1）在缺血性脑损伤中改善认知功能的潜力进行了体外、体内和体外评估。使用体外方法，我们预测了该化合物在大鼠模型中的药效和可能的安全性。此外，体外数据显示了化合物1的神经保护特性，这在新生大鼠皮质神经元培养物中谷氨酸兴奋毒性模型的体外实验中得到了进一步支持。接下来，我们检查了化合物1是否能够穿过完整和缺血动物的血脑屏障。化合物1改善了完整和缺血大鼠的动物行为，尽管完整脑中的浓度较低，但我们仍观察到明显的焦虑减少和活动增加。我们使用分子对接和分子动力学来支持我们的假设，即化合物1可能影响AMPA受体功能。在急性局灶性脑缺血大鼠模型中，我们研究了化合物1对行为和神经功能缺陷的影响。体内实验表明，化合物1显著减少了神经功能缺陷，并改善了神经症状恢复、探索行为和焦虑。因此，我们首次展示了化合物1可以被视为恢复认知功能的一种药物。
• Lactam-1-acetic acid carbalkoxymethyl esters and method for preparing
  申请人：——

  公开号：US05021568A1

  公开（公告）日：1991-06-04

  The present invention relates to organic chemistry. Lactam-1-acetic acid carbalkoxymethyl esters have the following general formula: ##STR1## wherein with R=H, n=1 or 3; with R=phenyl, n=1; R.sup.1 is an alkyl. A method for preparing said compounds comprises reacting lactams of the general formula: ##STR2## wherein with R=H, n=1 or 3, with R=phenyl n=1, with an alkali in a medium of aprotic solvents at a temperature of from 70.degree. to 130.degree. C., followed by the addition of an alkyl ester of a monohalcacetic acid to the resulting mixture and isolation of the desired product. The compounds according to the present invention are intermediate products in the synthesis of known biologically active substances.

  本发明涉及有机化学。Lactam-1-乙酸羧甲氧基甲酯具有以下通式：##STR1## 其中，当R=H，n=1或3时；当R=苯基，n=1时；R.sup.1是烷基。制备所述化合物的方法包括将通式为：##STR2## 当R=H，n=1或3时，当R=苯基，n=1时，与碱在无极溶剂介质中反应，反应温度为70℃至130℃，随后加入单卤代乙酸酯到所得混合物中，并分离所需产物。本发明所述化合物是已知生物活性物质合成的中间产物。
• US5021568A
  申请人：——

  公开号：US5021568A

  公开（公告）日：1991-06-04