2-((E)-But-2-enoylamino)-2-[2-(3-methoxy-phenyl)-2-oxo-ethyl]-malonic acid diethyl ester | 400017-91-6

• 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-((E)-But-2-enoylamino)-2-[2-(3-methoxy-phenyl)-2-oxo-ethyl]-malonic acid diethyl ester
• 英文别名: diethyl 2-[[(E)-but-2-enoyl]amino]-2-[2-(3-methoxyphenyl)-2-oxoethyl]propanedioate
• CAS: 400017-91-6
• 化学式: C₂₀H₂₅NO₇
• 分子量: 391.421
• InChiKey: PBUMGDYOLRSLOF-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-((E)-But-2-enoylamino)-2-[2-(3-methoxy-phenyl)-2-oxo-ethyl]-malonic acid diethyl ester 在 sodium hydroxide 、 溶剂黄146 作用下， 反应 2.33h， 生成 2-((E)-But-2-enoylamino)-4-(3-methoxy-phenyl)-4-oxo-butyric acid
  参考文献：
  名称：

  Inhibition of nNOS Activity in Rat Brain by Synthetic Kynurenines:  Structure−Activity Dependence

  摘要：

  The overstimulation of the N-methyl-D-aspartate (NMDA) subtype of glutamate receptors is involved in excitotoxicity, a process participating in neurodegeneration that characterizes some neurological disorders and acute cerebral insults. In looking for compounds with neuroprotective properties, a series of kynurenine derivatives were synthesized, and their effects on both the NMDA and nNOS activity in rat striatum were evaluated. Two compounds, 15a (2-acetamido-4-(2-amino-5-methoxyphenyl)-4-oxobutyric acid) and 15c (2-butyramido-4-(2-amino-5-methoxyphenyl)-4-oxobutyric acid), displayed more potent activities than the other synthetic compounds tested for the inhibition of NMDA excitability and nNOS activity. Two other compounds, 18a (2-acetamido-4-(3-methoxyphenyl)-4-oxobutyric acid) and 18c (2-butyramido-4-(3-methoxyphenyl)-4-oxobutyric acid), that have the same structure as 15a and 15c, except the amino group in R-1, showed different effects. Whereas compound 18a showed lower electrophysiological potency than compounds 15a and 15c in the inhibition of the NMDA-dependent excitability, compound 18c showed the opposite effect. Moreover, compounds 18a and 18c were unable to modify nNOS activity. The remaining kynurenines tested behave like compound 18a. These results suggest that a structure-related activity of these synthetic kynurenines and a N-H bond in a specific direction is necessary for some kynurenine analogues to inhibit nNOS activity.

  DOI：

  10.1021/jm010916w
• 作为产物：
  描述：

  2-溴-3‘-甲氧基苯乙酮 、 2-((E)-But-2-enoylamino)-malonic acid diethyl ester 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以85%的产率得到2-((E)-But-2-enoylamino)-2-[2-(3-methoxy-phenyl)-2-oxo-ethyl]-malonic acid diethyl ester
  参考文献：
  名称：

  Inhibition of nNOS Activity in Rat Brain by Synthetic Kynurenines:  Structure−Activity Dependence

  摘要：

  The overstimulation of the N-methyl-D-aspartate (NMDA) subtype of glutamate receptors is involved in excitotoxicity, a process participating in neurodegeneration that characterizes some neurological disorders and acute cerebral insults. In looking for compounds with neuroprotective properties, a series of kynurenine derivatives were synthesized, and their effects on both the NMDA and nNOS activity in rat striatum were evaluated. Two compounds, 15a (2-acetamido-4-(2-amino-5-methoxyphenyl)-4-oxobutyric acid) and 15c (2-butyramido-4-(2-amino-5-methoxyphenyl)-4-oxobutyric acid), displayed more potent activities than the other synthetic compounds tested for the inhibition of NMDA excitability and nNOS activity. Two other compounds, 18a (2-acetamido-4-(3-methoxyphenyl)-4-oxobutyric acid) and 18c (2-butyramido-4-(3-methoxyphenyl)-4-oxobutyric acid), that have the same structure as 15a and 15c, except the amino group in R-1, showed different effects. Whereas compound 18a showed lower electrophysiological potency than compounds 15a and 15c in the inhibition of the NMDA-dependent excitability, compound 18c showed the opposite effect. Moreover, compounds 18a and 18c were unable to modify nNOS activity. The remaining kynurenines tested behave like compound 18a. These results suggest that a structure-related activity of these synthetic kynurenines and a N-H bond in a specific direction is necessary for some kynurenine analogues to inhibit nNOS activity.

  DOI：

  10.1021/jm010916w

文献信息

• Inhibition of nNOS Activity in Rat Brain by Synthetic Kynurenines:  Structure−Activity Dependence
  作者：Encarnación Camacho、Josefa León、Adoración Carrión、Antonio Entrena、Germaine Escames、Huda Khaldy、Darío Acuña-Castroviejo、Miguel A. Gallo、Antonio Espinosa

  DOI：10.1021/jm010916w

  日期：2002.1.1

  The overstimulation of the N-methyl-D-aspartate (NMDA) subtype of glutamate receptors is involved in excitotoxicity, a process participating in neurodegeneration that characterizes some neurological disorders and acute cerebral insults. In looking for compounds with neuroprotective properties, a series of kynurenine derivatives were synthesized, and their effects on both the NMDA and nNOS activity in rat striatum were evaluated. Two compounds, 15a (2-acetamido-4-(2-amino-5-methoxyphenyl)-4-oxobutyric acid) and 15c (2-butyramido-4-(2-amino-5-methoxyphenyl)-4-oxobutyric acid), displayed more potent activities than the other synthetic compounds tested for the inhibition of NMDA excitability and nNOS activity. Two other compounds, 18a (2-acetamido-4-(3-methoxyphenyl)-4-oxobutyric acid) and 18c (2-butyramido-4-(3-methoxyphenyl)-4-oxobutyric acid), that have the same structure as 15a and 15c, except the amino group in R-1, showed different effects. Whereas compound 18a showed lower electrophysiological potency than compounds 15a and 15c in the inhibition of the NMDA-dependent excitability, compound 18c showed the opposite effect. Moreover, compounds 18a and 18c were unable to modify nNOS activity. The remaining kynurenines tested behave like compound 18a. These results suggest that a structure-related activity of these synthetic kynurenines and a N-H bond in a specific direction is necessary for some kynurenine analogues to inhibit nNOS activity.