trans-2,5-dicarboxy-1,4-piperazinediacetic acid | 96705-83-8

• 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: trans-2,5-dicarboxy-1,4-piperazinediacetic acid
• 英文别名: (2S,5R)-1,4-bis(carboxymethyl)piperazine-2,5-dicarboxylic acid
• CAS: 96705-83-8
• 化学式: C₁₀H₁₄N₂O₈
• 分子量: 290.23
• InChiKey: OAEXJHXBIDZYHT-OLQVQODUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  156
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  trans-2,5-dicarboxy-1,4-piperazinediacetic acid 在 盐酸 、 氨 作用下， 以 甲醇 为溶剂， 反应 53.0h， 生成 trans-1,4-bis(2-amino-2-oxoethyl)-2,5-piperazinedicarboxamide
  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：

  溴乙酸 、 (2R,5S)-2,5-哌嗪二甲酸 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 24.0h， 以87.6%的产率得到trans-2,5-dicarboxy-1,4-piperazinediacetic acid
  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

文献信息

• NAIR, RAGHUNATHAN V.;WITIAK, DONALD T.
  作者：NAIR, RAGHUNATHAN V.、WITIAK, DONALD T.

  DOI：——

  日期：——
• WITIAK, D. T.;NAIR, RAGHUNATHAN, V.;SCHMID, F. A., J. MED. CHEM., 1985, 28, N 9, 1228-1234
  作者：WITIAK, D. T.、NAIR, RAGHUNATHAN, V.、SCHMID, F. A.

  DOI：——

  日期：——
• US4871736A
  申请人：——

  公开号：US4871736A

  公开（公告）日：1989-10-03