1,2-二(3,5-二氧代哌嗪-1-基)乙烷 | 1506-47-4

• 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
• 中文名称: 1,2-二(3,5-二氧代哌嗪-1-基)乙烷
• 英文名称: 1,2-bis(3,5-dioxopiperazin-1-yl)-ethane
• 英文别名: 1,2 bis(3,5 dioxo 1 piperazinyl)ethane；ICRF-154；4,4'-ethane-1,2-diyl-bis-piperazine-2,6-dione；1,2-bis-(3,5-dioxopiperazin-1-yl)ethane；1,2-bis(3,5-dioxopiperazin-1-yl)ethane；1,2-Bis-(3,5-dioxopiperazin-1-yl)-aethan；4-[2-(3,5-dioxopiperazin-1-yl)ethyl]piperazine-2,6-dione
• CAS: 1506-47-4
• 化学式: C₁₀H₁₄N₄O₄
• 分子量: 254.246
• InChiKey: GBLIGNUYGOFIKS-UHFFFAOYSA-N

物化性质

• 熔点：
  295-300 °C
• 沸点：
  539.9±50.0 °C(Predicted)
• 密度：
  1.361±0.06 g/cm3(Predicted)
• 溶解度：
  二氯甲烷/甲醇（8:2）；二甲基亚砜；甲醇（加热）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2933599090
• 储存条件：
  2-8℃

反应信息

• 作为反应物：
  描述：

  1,2-二(3,5-二氧代哌嗪-1-基)乙烷 在 吡啶 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 1,2-bis(4-n-butoxycarbonyloxymethyl-3,5-dioxopiperazin-1-yl)ethane
  参考文献：
  名称：

  Synthesis and antitumor properties of N1-acyloxymethyl derivatives of bis(2,6-dioxopiperazines).

  摘要：

  许多双(2,6-二氧哌嗪)I、ICRF-154的N1-酰氧甲基衍生物VI被制备并测试了其抗肿瘤活性。将I与甲醛反应得到结晶的双(N1-羟甲基)衍生物VII，该衍生物在不同条件下酰化得到双(N1-酰氧甲基)衍生物VI。研究了VI对小鼠P388白血病的抗肿瘤活性。发现几种双(N1-酰氧甲基)化合物如苯乙酰氧甲基VI-6、甲氧羰基氧甲基VI-41、异丁氧羰基氧甲基VI-44和呋喃甲酰甲基VI-38具有强大的抗肿瘤活性。另一方面，酰基中含有氨基或羧酸功能的水溶性酯类显示出较低的活性。这些双(N-1-酰氧甲基)衍生物VI可能通过体内非特异性酯酶水解为母体双(2,6-二氧哌嗪)I来展现其抗肿瘤活性。

  DOI：

  10.1248/cpb.37.2976
• 作为产物：
  描述：

  尿素 、 乙二胺四乙酸 以57%的产率得到
  参考文献：
  名称：

  JARY, JIRI;KOSTKAN, JAN;GROSSMANN, VOJTECH;MATERNOVA, MILUSE;POTACOVA, MI+

  摘要：

  DOI：

文献信息

• Bis-dioxopiperazine derivatives, process for their preparation,
  申请人：Zenyaku Kogyo Kabushiki Kaisha

  公开号：US04650799A1

  公开（公告）日：1987-03-17

  Disclosed are novel bis-dioxopiperazine derivatives and non-toxic salts thereof, process for their preparation, antitumor agents comprising them and compositions containing them. The bis-dioxopiperazine derivatives are represented by the following general formula (I): ##STR1## wherein R represents an alkyl radical having 1 to 17 carbon atoms, a cycloalkyl radical having 3 to 7 carbon atoms, a lower alkyl radical having a substituent or substituents selected from the group consisting of halogeno, carboxy, alkoxycarbonyl having 2 to 5 carbon atoms, lower alkoxy, substituted or unsubstituted phenoxy, naphthyloxy, substituted or unsubstituted phenylthio, substituted or unsubstituted phenyl and naphthyl, a substituted or unsubstituted phenyl lower alkenyl radical, a substituted or unsubstituted phenyl radical, a naphthyl radical, a heterocyclic radical selected from the group consisting of pyridyl, furyl and thienyl, an alkoxy radical having 1 to 8 carbon atoms, a substituted or unsubstituted phenyl lower alkoxy radical, or a substituted or unsubstituted phenoxy radical. A substituent or substituents on R may be selected from the group consisting of lower alkyl, halogeno, lower alkoxy, acyloxy having 2 to 5 carbon atoms, methylenedioxy, carboxy, amino, methanesulfonylamino and nitro. The above-mentioned "lower alkyl", "lower alkoxy" and "lower alkenyl" respectively refer to alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms and alkenyl having 2 to 4 carbon atoms.

  揭示了新颖的双二氧哌嗪衍生物及其无毒盐，其制备方法，包含它们的抗肿瘤剂和含有它们的组合物。双二氧哌嗪衍生物由以下一般式（I）表示：##STR1##其中R代表具有1至17个碳原子的烷基基团，具有3至7个碳原子的环烷基基团，具有来自卤素、羧基、具有2至5个碳原子的烷氧羰基、辅基或辅基的下位烷氧基、取代或未取代的苯氧基、萘氧基、取代或未取代的苯硫基、取代或未取代的苯基和萘基、取代或未取代的苯下位烯基基团、取代或未取代的苯基基团、萘基团、选自吡啶基、呋喃基和噻吩基的杂环基团、具有1至8个碳原子的烷氧基、取代或未取代的苯下位烷氧基团，或取代或未取代的苯氧基团。R上的辅基或辅基可选自下位烷基、卤素、下位烷氧基、具有2至5个碳原子的酰氧基、亚甲二氧基、羧基、氨基、甲磺酰氨基和硝基的群。上述“下位烷基”、“下位烷氧基”和“下位烯基”分别指具有1至4个碳原子的烷基，具有1至4个碳原子的烷氧基和具有2至4个碳原子的烯基。
• Bis-dioxopiperazine derivatives, antitumor agents comprising them and
  申请人：Zenyaki Kogyo Kabushiki Kaisha

  公开号：US04737497A1

  公开（公告）日：1988-04-12

  Disclosed are novel bis-dioxopiperazine derivatives, process for their preparation, antitumor agents comprising them and compositions containing them. The bis-dioxopiperazine derivatives are represented by the following general formula (I): ##STR1## wherein R.sub.1 represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms; R.sub.2 represents a hydrogen atom or a group of ##STR2## R.sub.3 and R.sub.4, which are respectively independent and are the same or different, represent respectively a lower alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms or a heterocyclic radical selected from the group consisting of substituted or unsubstituted piperidino, substituted or unsubstituted piperazino, substituted or unsubstituted morpholino and substituted or unsubstituted thiomorpholino, or R.sub.3 and R.sub.4 are bonded together to form a group of ##STR3## which represents a cyclic amino group selected from the group consisting of substituted or unsubstituted pyrrolidino, substituted or unsubstituted piperidino, substituted or unsubstituted piperazino, substituted or unsubstituted morpholino, substituted or unsubstituted thiomorpholino and substituted or unsubstituted thiadiazino; and the substituents of the heterocyclic radical and the cyclic amino group are selected from the group consisting of a lower alkyl group having 1 to 4 carbon atoms, oxo and phenyl, said cyclic amino group being not morpholino when R.sub.1 is a hydrogen atom and R.sub.2 is the group of ##STR4##

  本发明涉及新型的双二氧哌嗪衍生物，其制备方法，包含它们的抗肿瘤药物以及含有它们的组合物。双二氧哌嗪衍生物由以下一般式（I）表示：其中R.sub.1代表氢原子或具有1至4个碳原子的较低烷基基团；R.sub.2代表氢原子或##STR2##基团；R.sub.3和R.sub.4分别独立且相同或不同，分别表示具有1至4个碳原子的较低烷基基团，具有3至7个碳原子的环烷基基团或从取代或未取代哌啶基、取代或未取代哌嗪基、取代或未取代吗啉基和取代或未取代硫代吗啉基中选择的杂环基团，或者R.sub.3和R.sub.4结合在一起形成##STR3##基团，表示从取代或未取代吡咯啉基、取代或未取代哌啶基、取代或未取代哌嗪基、取代或未取代吗啉基、取代或未取代硫代吗啉基和取代或未取代噻二唑基中选择的环氨基基团；并且杂环基团和环氨基基团的取代基选择自具有1至4个碳原子的较低烷基基团、氧代基和苯基的群，当R.sub.1为氢原子且R.sub.2为##STR4##基团时，所述环氨基基团不是吗啉基。
• Fischer; Moller; Budnowski, Arzneimittel-Forschung/Drug Research, 1984, vol. 34, # 6, p. 663 - 668
  作者：Fischer、Moller、Budnowski、et al.

  DOI：——

  日期：——
• Bis-dioxopiperazine derivatives, process for their preparation, antitumor agents comprising them and compositions containing them
  申请人：ZENYAKU KOGYO KABUSHIKI KAISHA

  公开号：EP0140327B1

  公开（公告）日：1990-05-23
• SHU, WEI, IYAO GUNE, 19,(1988) N, S. 363-365
  作者：SHU, WEI

  DOI：——

  日期：——