3,6-bis(2-methoxybenzylidene)piperazine-2,5-dione | 413591-32-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,6-bis(2-methoxybenzylidene)piperazine-2,5-dione
• 英文别名: 3,6-Bis[(2-methoxyphenyl)methylidene]piperazine-2,5-dione
• CAS: 413591-32-9
• 化学式: C₂₀H₁₈N₂O₄
• 分子量: 350.374
• InChiKey: SVXGBEWJMBBCQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-bis(2-methoxybenzylidene)piperazine-2,5-dione 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到3,6-bis[(2-methoxyphenyl)methylidene]-1,4-dimethylpiperazine-2,5-dione
  参考文献：
  名称：

  Diastereoselective Synthesis of Diketopiperazine Bis-α,β-epoxides

  摘要：

  Functionalized diketopiperazines (dioxopiperazines) are an important class of molecules in medicinal chemistry and material science. Herein we report a diastereoselective synthesis of diketopiperazine bis-alpha,beta-epoxides via the oxidation of exocyclic olefins. Although six diastereomers may be formed by this approach, only one or two of them were observed.

  DOI：

  10.1021/jo102096d
• 作为产物：
  描述：

  1,4-二乙酰基哌嗪-2,5-二酮 、 邻甲氧基苯甲醛 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 以56%的产率得到3,6-bis(2-methoxybenzylidene)piperazine-2,5-dione
  参考文献：
  名称：

  Diastereoselective Synthesis of Diketopiperazine Bis-α,β-epoxides

  摘要：

  Functionalized diketopiperazines (dioxopiperazines) are an important class of molecules in medicinal chemistry and material science. Herein we report a diastereoselective synthesis of diketopiperazine bis-alpha,beta-epoxides via the oxidation of exocyclic olefins. Although six diastereomers may be formed by this approach, only one or two of them were observed.

  DOI：

  10.1021/jo102096d

文献信息

• Design and synthesis of novel soluble 2,5-diketopiperazine derivatives as potential anticancer agents
  作者：Shengrong Liao、Xiaochu Qin、Ding Li、Zhengchao Tu、Jinsheng Li、Xuefeng Zhou、Junfeng Wang、Bin Yang、Xiuping Lin、Juan Liu、Xianwen Yang、Yonghong Liu

  DOI：10.1016/j.ejmech.2014.06.030

  日期：2014.8

  Non-protected 2,5-diketopiperazine derivatives have poor solubility thus with negative impact on their bioavailability. In the present study, twenty-one novel soluble mono-protected, and three non-protected 2,5-diketopiperazine derivatives were designed and synthesized. Their anticancer activity to ten cell lines were evaluated by using CCK8 assay, and the results showed that about half of the mono-protected derivatives had broad-spectrum anticancer activity. Among allyl-protected derivatives, compound 4m had strong activity to all the cell lines (IC50 = 0.5-4.5 μM), especially to the cancer cell lines U937 (IC50 = 0.5 μM) and K562 (IC50 = 0.9 μM). Compound 4m could become a lead compound for further development for anticancer agents.
• Diastereoselective Synthesis of Diketopiperazine Bis-α,β-epoxides
  作者：Shin Ando、Amy L. Grote、Kazunori Koide

  DOI：10.1021/jo102096d

  日期：2011.2.18

  Functionalized diketopiperazines (dioxopiperazines) are an important class of molecules in medicinal chemistry and material science. Herein we report a diastereoselective synthesis of diketopiperazine bis-alpha,beta-epoxides via the oxidation of exocyclic olefins. Although six diastereomers may be formed by this approach, only one or two of them were observed.