ethyl 2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate | 75096-47-8

• 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: ethyl 2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate
• 英文别名: ethyl 2-(5-methyl-2,4-dioxopyrimidin-1-yl)propanoate
• CAS: 75096-47-8
• 化学式: C₁₀H₁₄N₂O₄
• 分子量: 226.232
• InChiKey: TWQHQXLJQRFAKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.03
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.16
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate 在 4-二甲氨基吡啶 、 hydrazine hydrate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 4-(1-(heptan-4-yl)-2-(2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoyl)hydrazinecarbonyl)phenyl acetate
  参考文献：
  名称：

  Design and synthesis of N-alkyl-N′-substituted 2,4-dioxo-3,4-dihydropyrimidin-1-diacylhydrazine derivatives as ecdysone receptor agonist

  摘要：

  Based on the discovery of thymine as an ecdysteroid agonist, a series of 1,4-disubstituted diacylhydrazine derivatives with a thymine moiety were designed and synthesized. The activities of these compounds against Spodoptera litura (Fabricius) were evaluated by the insect immersion method. Results showed that compound 2h with an N-cyclohexylmethyl substituent exhibits the most potent agonist activity with a median lethal concentration of 23.21 mu g/mL. This compound also caused malformation of molting larvae and adults. Compound 2h was further demonstrated as an ecdysteroid agonist by reporter gene assay on the Spodoptera frugiperda cell line (Sf9 cells). A molecular docking study indicated that hydrophobic interactions and the formation of hydrogen bonds between the compounds and the ecdysone receptor play critical roles in promoting the binding affinity of the compound. The structure of compound 2h may serve as a favorable template for the development of new ecdysteroid agonists with a pyrimidinedione moiety. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.010
• 作为产物：
  描述：

  胸腺嘧啶 、 2-氯丙酸乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以87%的产率得到ethyl 2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate
  参考文献：
  名称：

  Design and synthesis of N-alkyl-N′-substituted 2,4-dioxo-3,4-dihydropyrimidin-1-diacylhydrazine derivatives as ecdysone receptor agonist

  摘要：

  Based on the discovery of thymine as an ecdysteroid agonist, a series of 1,4-disubstituted diacylhydrazine derivatives with a thymine moiety were designed and synthesized. The activities of these compounds against Spodoptera litura (Fabricius) were evaluated by the insect immersion method. Results showed that compound 2h with an N-cyclohexylmethyl substituent exhibits the most potent agonist activity with a median lethal concentration of 23.21 mu g/mL. This compound also caused malformation of molting larvae and adults. Compound 2h was further demonstrated as an ecdysteroid agonist by reporter gene assay on the Spodoptera frugiperda cell line (Sf9 cells). A molecular docking study indicated that hydrophobic interactions and the formation of hydrogen bonds between the compounds and the ecdysone receptor play critical roles in promoting the binding affinity of the compound. The structure of compound 2h may serve as a favorable template for the development of new ecdysteroid agonists with a pyrimidinedione moiety. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.010