cis-tetrahydrodipyrazino<1,2-a:1',2'-d>pyrazine-1,3,7,9(2H,4H,8H,10H)-tetralone | 92927-69-0

• 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: cis-tetrahydrodipyrazino<1,2-a:1',2'-d>pyrazine-1,3,7,9(2H,4H,8H,10H)-tetralone
• 英文别名: cis-tetrahydrodipyrazino[1,2-a:1',2'-d]pyrazine-1,3,7,9(2H,4H,8H,10H)-tetralone
• CAS: 92927-69-0
• 化学式: C₁₀H₁₂N₄O₄
• 分子量: 252.23
• InChiKey: RAINMJGOXSBWFS-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.35
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  98.82
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  吗啉 、 聚合甲醛 、 cis-tetrahydrodipyrazino<1,2-a:1',2'-d>pyrazine-1,3,7,9(2H,4H,8H,10H)-tetralone 以 二甲基亚砜 为溶剂， 反应 5.0h， 以85.95%的产率得到cis-tetrahydro-2,8-bis(4-morpholinomethyl)dipyzino<1,2-a:1',2'-d>pyrazine-1,3,7,9(2H,4H,8H,10H)-tetralone
  参考文献：
  名称：

  Synthesis and antimetastatic properties of stereoisomeric tricyclic bis(dioxopiperazines) in the Lewis lung carcinoma model

  摘要：

  Synthesis of trans- and cis-tetrahydrodipyrazino[1,2-a:1',2'-d] pyrazine-1,3,7,9(2H,4H,8H,10H)-tetrone analogues 10 and 11 belonging to the bis(dioxopiperazine) class of antitumor agents and their bis(morpholinomethyl) derivatives 12 and 13 are described with use of 2,5-dimethylpyrazine as the starting material. Synthetic studies utilizing 3,6-disubstituted 2,5-dioxopiperazine precursors are included. Evaluation of 10-13 in the Lewis Lung carcinoma model indicated the bis(morpholinomethyl) analogue cis-13 to be antimetastatic, whereas the trans isomer 12 was toxic at a similar dose effecting a decrease in the life span of treated mice. The parent bis(dioxopiperazines) 10 and 11 were ineffective as antitumor or antimetastatic drugs.

  DOI：

  10.1021/jm00147a018
• 作为产物：
  描述：

  dimethyl cis-Piperazine-2,5-dicarboxylate 在 氨 、 sodium ethanolate 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 二甲基亚砜 为溶剂， 反应 78.0h， 生成 cis-tetrahydrodipyrazino<1,2-a:1',2'-d>pyrazine-1,3,7,9(2H,4H,8H,10H)-tetralone
  参考文献：
  名称：

  Synthesis and antimetastatic properties of stereoisomeric tricyclic bis(dioxopiperazines) in the Lewis lung carcinoma model

  摘要：

  Synthesis of trans- and cis-tetrahydrodipyrazino[1,2-a:1',2'-d] pyrazine-1,3,7,9(2H,4H,8H,10H)-tetrone analogues 10 and 11 belonging to the bis(dioxopiperazine) class of antitumor agents and their bis(morpholinomethyl) derivatives 12 and 13 are described with use of 2,5-dimethylpyrazine as the starting material. Synthetic studies utilizing 3,6-disubstituted 2,5-dioxopiperazine precursors are included. Evaluation of 10-13 in the Lewis Lung carcinoma model indicated the bis(morpholinomethyl) analogue cis-13 to be antimetastatic, whereas the trans isomer 12 was toxic at a similar dose effecting a decrease in the life span of treated mice. The parent bis(dioxopiperazines) 10 and 11 were ineffective as antitumor or antimetastatic drugs.

  DOI：

  10.1021/jm00147a018