trans-piperazine-2,5-dicarboxamide | 96705-95-2

• 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-piperazine-2,5-dicarboxamide
• 英文别名: trans-Piperazine 2,5-dicarboxamide；(2S,5R)-piperazine-2,5-dicarboxamide
• CAS: 96705-95-2
• 化学式: C₆H₁₂N₄O₂
• 分子量: 172.187
• InChiKey: ZPLAAFHVWGFGGQ-ZXZARUISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  110
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-piperazine-2,5-dicarboxamide 在 sodium ethanolate 、 potassium carbonate 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 34.0h， 生成 trans-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：

  cis-piperazine-2,5-carboxylic acid 在 盐酸 、 氨 作用下， 以 甲醇 为溶剂， 反应 60.0h， 生成 trans-piperazine-2,5-dicarboxamide
  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

• Stereoisomeric tricyclic bis(dioxopiperazines) and pharmaceutical
  申请人：The Ohio State University

  公开号：US04871736A1

  公开（公告）日：1989-10-03

  Stereoisomeric tricyclic bis(dioxopiperazines) of the formula ##STR1## wherein R is H or ##STR2## and the processes for the synthesis thereof are provided. The compounds are effective as antitumor or antimetastatic drugs.

  提供公式为##STR1##的立体异构三环双二酮哌嗪化合物，其中R为H或##STR2##的合成方法。这些化合物作为抗肿瘤或抗转移药物具有有效性。
• 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
• Synthesis and antimetastatic properties of stereoisomeric tricyclic bis(dioxopiperazines) in the Lewis lung carcinoma model
  作者：Donald T. Witiak、Raghunathan V. Nair、Franz A. Schmid

  DOI：10.1021/jm00147a018

  日期：1985.9

  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.