1,4-bis(4-methoxybenzyl)piperazine-2,5-dione | 92097-99-9

• 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: 1,4-bis(4-methoxybenzyl)piperazine-2,5-dione
• 英文别名: 1,4-bis(p-methoxybenzyl)-2,5-piperazinedione；1,4-di(p-methoxybenzyl)piperazine-2,5-dione；1,4-bis-(4-methoxy-benzyl)-piperazine-2,5-dione；1,4-Bis-(4-methoxy-benzyl)-piperazin-2,5-dion；1,4-Bis[(4-methoxyphenyl)methyl]piperazine-2,5-dione
• CAS: 92097-99-9
• 化学式: C₂₀H₂₂N₂O₄
• 分子量: 354.406
• InChiKey: VXFOYPCCMGBBMN-UHFFFAOYSA-N

物化性质

• 熔点：
  206 °C
• 沸点：
  611.7±55.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-bis(4-methoxybenzyl)piperazine-2,5-dione 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 0.5h， 生成 3,6-dibromo-1,4-di(p-methoxybenzyl)piperazine-2,5-dione
  参考文献：
  名称：

  Monosubstitution of Symmetrical Piperazine-2,5-dione Derivatives

  摘要：

  通过简单的一锅法，对甘氨酸酐衍生物进行溴化和甲醇分解，可得到相应的 3-溴和 3-甲氧基取代的哌嗪-2,5-二酮衍生物。

  DOI：

  10.1071/ch9901455
• 作为产物：
  描述：

  甘氨酸酐 在 sodium methylate 作用下， 生成 1,4-bis(4-methoxybenzyl)piperazine-2,5-dione
  参考文献：
  名称：

  Graenacher; Wolf; Weidinger, Helvetica Chimica Acta, 1928, vol. 11, p. 1234

  摘要：

  DOI：

文献信息

• Studies towards complex bridged alkaloids: regio- and stereocontrolled enolate chemistry of 2,5-diketopiperazines
  作者：Mark Pichowicz、Nigel S. Simpkins、Alexander J. Blake、Claire Wilson

  DOI：10.1016/j.tet.2008.02.020

  日期：2008.4

  N-protected diketopiperazines (DKPs) via enolate intermediates has been studied. The enolate reactions were highly diastereocontrolled, leading to enantiopure DKP products if chiral amino acid precursors were employed, and giving racemic products, starting with centrosymmetric DKPs, even when a chiral lithium amide base was used to generate the lithium enolate. With unsymmetrical DKPs derived from proline

  已经研究了通过烯醇化物中间体取代对称的N-保护的二酮哌嗪（DKP）。烯醇盐的反应是高度非对映体控制的，如果使用手性氨基酸前体，则会产生对映体纯的DKP产物，即使使用手性锂酰胺碱生成烯醇酸锂，也可以从中心对称的DKPs开始生成外消旋产物。对于衍生自脯氨酸和丙氨酸，苯丙氨酸或缬氨酸的不对称DKP，烯醇取代发生在脯氨酸残基上，具有很高的区域选择性和立体选择性。这样就可以合成取代的DKP，该化合物可以通过阳离子过程环化，得到天然产物对乙酰氨基酚和Stephacid中存在的双环[2.2.2]二氮杂辛烷核心结构。
• [EN] EPIDITHIODIOXOPIPERAZINE COMPOUND OR ITS DERIVATIVES, AND THE USE THEREOF<br/>[FR] COMPOSÉ ÉPIDITHIODIOXOPIPÉRAZINE OU SES DÉRIVÉS, ET LEUR UTILISATION
  申请人：UNIV EWHA IND COLLABORATION

  公开号：WO2014189343A1

  公开（公告）日：2014-11-27

  The present invention relates to an epidithiodioxopiperazine derivative represented by the Chemical Formula 1 or its reduced derivative; a method for preparing a compound represented by Chemical Formula 1 having improved intracellular permeability and mimicking the activity of 2-Cys-Prx in its reduced form in the cells; a pharmaceutical composition for preventing or treating vascular diseases comprising an epidithiodioxopiperazine compound or its derivatives or pharmaceutically acceptable salts thereof as an active ingredient; a drug delivery device for local administration including the pharmaceutical composition; and a pharmaceutical composition for inhibiting melanoma metastasis comprising the epidithiodioxopiperazine compound or its derivatives or pharmaceutically acceptable salts thereof as an active ingredient.

  本发明涉及一种由化学式1表示的二硫代二氧哌嗪衍生物或其还原衍生物；一种制备化学式1所代表的化合物的方法，该化合物具有改善细胞内渗透性并在细胞中模拟其还原形式中2-Cys-Prx的活性；一种用作预防或治疗血管疾病的药物组合物，其包括二硫代二氧哌嗪化合物或其衍生物或其药用盐作为活性成分；一种用于局部给药的药物递送装置，包括该药物组合物；以及一种用作抑制黑色素瘤转移的药物组合物，其包括二硫代二氧哌嗪化合物或其衍生物或其药用盐作为活性成分。
• EPIDITHIODIOXOPIPERAZINE COMPOUND OR ITS DERIVATIVES, AND THE USE THEREOF
  申请人：EWHA University-Industry Collaboration Foundation

  公开号：US20160222031A1

  公开（公告）日：2016-08-04

  The present invention relates to an epidithiodioxopiperazine derivative represented by the following Chemical Formula 1 or its reduced derivative; a method for preparing a compound represented by Chemical Formula 1 having improved intracellular permeability and mimicking the activity of 2-Cys-Prx in its reduced form in the cells; a pharmaceutical composition for preventing or treating vascular diseases comprising an epidithiodioxopiperazine compound or its derivatives or pharmaceutically acceptable salts thereof as an active ingredient; a drug delivery device for local administration including the pharmaceutical composition; and a pharmaceutical composition for inhibiting melanoma metastasis comprising the epidithiodioxopiperazine compound or its derivatives or pharmaceutically acceptable salts thereof as an active ingredient.

  本发明涉及以下化学式1所表示的表皮二硫二氧哌嗪衍生物或其还原衍生物；一种制备化学式1所表示的化合物的方法，该方法具有改善细胞内渗透性并在其还原形式下模拟2-Cys-Prx在细胞中的活性；一种预防或治疗血管疾病的制药组合物，包括表皮二硫二氧哌嗪化合物或其衍生物或其药学上可接受的盐作为活性成分；一种用于局部给药的药物递送装置，包括该制药组合物；以及一种抑制黑色素瘤转移的制药组合物，包括表皮二硫二氧哌嗪化合物或其衍生物或其药学上可接受的盐作为活性成分。
• Epidithiodioxopiperazine compound or its derivatives, and the use thereof
  申请人：VASTHERA Co. Ltd.

  公开号：US10450327B2

  公开（公告）日：2019-10-22

  The present invention relates to an epidithiodioxopiperazine derivative represented by the following Chemical Formula 1 or its reduced derivative; a method for preparing a compound represented by Chemical Formula 1 having improved intracellular permeability and mimicking the activity of 2-Cys-Prx in its reduced form in the cells; a pharmaceutical composition for preventing or treating vascular diseases comprising an epidithiodioxopiperazine compound or its derivatives or pharmaceutically acceptable salts thereof as an active ingredient; a drug delivery device for local administration including the pharmaceutical composition; and a pharmaceutical composition for inhibiting melanoma metastasis comprising the epidithiodioxopiperazine compound or its derivatives or pharmaceutically acceptable salts thereof as an active ingredient.

  本发明涉及一种由以下化学式1代表的表二硫代二酮哌嗪衍生物或其还原衍生物；一种制备由化学式1代表的化合物的方法，该化合物具有更好的细胞内渗透性，并能模拟细胞内还原形式的2-Cys-Prx的活性；一种用于预防或治疗血管疾病的药物组合物，其活性成分包括表二硫基二氧代哌嗪化合物或其衍生物或其药学上可接受的盐类；一种用于局部给药的给药装置，其活性成分包括该药物组合物；以及一种用于抑制黑色素瘤转移的药物组合物，其活性成分包括表二硫基二氧代哌嗪化合物或其衍生物或其药学上可接受的盐类。
• Divergent, generalized synthesis of unsymmetrically substituted 2,5-piperazinediones
  作者：Robert M. Williams、Robert W. Armstrong、Lynn K. Maruyama、Jen Sen Dung、Oren P. Anderson

  DOI：10.1021/ja00297a034

  日期：1985.5