diethyl (m-nitrophenacyl)acetamidomalonate | 153212-73-8

• 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: diethyl (m-nitrophenacyl)acetamidomalonate
• 英文别名: Diethyl 2-acetamido-2-[2-(3-nitrophenyl)-2-oxoethyl]propanedioate
• CAS: 153212-73-8
• 化学式: C₁₇H₂₀N₂O₈
• 分子量: 380.354
• InChiKey: XVJIQQOZNTYLID-UHFFFAOYSA-N

物化性质

• 沸点：
  569.7±50.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  145
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diethyl (m-nitrophenacyl)acetamidomalonate 在 sodium hydroxide 作用下， 反应 2.0h， 生成
  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'-硝基苯乙酮 、 乙酰氨基丙二酸二乙酯 在 sodium hydride 作用下， 生成 diethyl (m-nitrophenacyl)acetamidomalonate
  参考文献：
  名称：

  犬尿氨酸途径的调节以寻找新的神经保护剂。合成和初步评估（间硝基苯甲酰基）丙氨酸，一种有效的犬尿氨酸3-羟化酶抑制剂。

  摘要：

  （o-硝基苯甲酰基）-，（间硝基苯甲酰基）-和（对硝基苯甲酰基）丙氨酸（邻-，间-和p-NBA），三种新的犬尿氨酸类似物的合成及其作为犬尿氨酸酶和尿囊素抑制剂的评估报告了犬尿氨酸-3-羟化酶。这些化合物中最有效的化合物m-NBA，作为犬尿氨酸3-羟化酶的抑制剂的IC50为0.9 +/- 0.1 microM，作为犬尿氨酸酶的抑制剂的IC50为100 +/- 12 microM。当对大鼠给药时，m-NBA会显着增加大脑以及血液和肝脏中犬尿氨酸和犬尿酸的浓度。m-NBA还被证明可以增加海马细胞外液中犬尿酸的浓度。这种增加与镇静和抗惊厥活动有关，

  DOI：

  10.1021/jm00031a015