3,6-epidithio-1,3,4,6-tetramethyl-2,5-dioxopiperazine | 53338-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3,6-epidithio-1,3,4,6-tetramethyl-2,5-dioxopiperazine
• 英文别名: 1,4,5,7-tetramethyl-2,3-dithia-5,7-diazabicyclo[2.2.2]octane-6,8-dione
• CAS: 53338-36-6
• 化学式: C₈H₁₂N₂O₂S₂
• 分子量: 232.327
• InChiKey: JNACNFRANQECFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  91.2
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3,6-epidithio-1,3,4,6-tetramethyl-2,5-dioxopiperazine 在 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 生成 1,3,4,6-Tetramethyl-3,6-epithio-2,5-dioxopiperazine
  参考文献：
  名称：

  Biosynthesis of gliotoxin. Synthesis of sulfur-bridged dioxopiperazines from N-hydroxyamino acids

  摘要：

  DOI：

  10.1021/jo01298a024
• 作为产物：
  描述：

  1,3-Dimethyl-3-methoxy-6-methylene-2,5-dioxopiperazine 在 吡啶 、 硫化氢 、 碘 、 potassium carbonate 、 zinc(II) chloride 作用下， 生成 3,6-epidithio-1,3,4,6-tetramethyl-2,5-dioxopiperazine
  参考文献：
  名称：

  Biosynthesis of gliotoxin. Synthesis of sulfur-bridged dioxopiperazines from N-hydroxyamino acids

  摘要：

  DOI：

  10.1021/jo01298a024

文献信息

• Thiolation of symmetrical and unsymmetrical diketopiperazines
  作者：Bettina M. Ruff、Sabilla Zhong、Martin Nieger、Stefan Bräse

  DOI：10.1039/c2ob06663g

  日期：——

  The introduction of sulfur units into a variety of symmetrical and unsymmetrical diketopiperazines (DKPs) is described. We investigated different thiolation methods utilizing several bases and electrophilic sulfur reagents, leading to monomethylthio-, bis(methylthio)-, and epithio-DKPs. Their formation proceeded diastereoselectively, facilitating the application in total syntheses of many thiodiketopiperazine (TDKP) natural products. Furthermore, possible side reactions as well as mechanistic studies and stereochemical structural assignments of the obtained products are given.

  本文介绍了将硫单元引入各种对称和不对称二酮哌嗪（DKPs）的方法。我们利用几种碱和亲电硫试剂研究了不同的硫代方法，从而得到了单甲硫基、双（甲硫基）和表硫基 DKPs。它们的形成是非对映选择性的，有利于应用于许多硫代二酮哌嗪（TDKP）天然产物的全合成。此外，还给出了可能的副反应以及所获产物的机理研究和立体化学结构分配。
• Synthesis of sulfur-bridged piperazinediones by reaction of 3,6-dibromo-1,4-dimethyl-2,5-piperazinedione with<i>geminal</i>dithiols
  作者：Ananthachari Srinivasan、Aldean J. Kolar、Richard K. Olsen

  DOI：10.1002/jhet.5570180811

  日期：1981.12

  the 3,6-position with a geminal dithiol-bridging group. These sulfur-bridged piperazinediones formally represent derivatives of the 2,4-dithia-6,8-diaza-7,9-dioxobicyclo[3.2.2]nonane ring system. Attempts to transform these sulfur-bridged piperazinediones to 3,6-epidithiopiperazinediones by removal of the bridging group common to the sulfur functionality were unsuccessful. Studies also are reported of

  几个反应偕二硫醇与3,6-二溴-1,4-二甲基-2,5-哌嗪二酮在3,6-位被取代的良好的产率哌嗪衍生物，得到偕二硫醇桥接基团。这些硫桥联哌嗪二酮正式代表2,4-二硫-6,8-二氮杂-7,9-二氧代双环[3.2.2]壬烷环系统的衍生物。通过除去硫官能团共有的桥连基团，尝试将这些硫桥连的哌嗪二酮转化为3，6-表二硫代哌嗪二酮是不成功的。还报道了将硫代乙酸加到3，6-二亚甲基-2，5-哌嗪二酮中得到3，6-二乙酰硫基-3，6-二甲基-2，5-哌嗪二酮的研究。将3，6-二乙酰硫基衍生物转化为表硫基哌嗪二酮环系统，得到表二硫代哌嗪和表二硫代哌嗪二酮的混合物。
• 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。
• PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING SOLID CANCER, CONTAINING EPIDITHIODIOXOPIPERAZINE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF
  申请人：VASTHERA Co. Ltd.

  公开号：EP4023224A1

  公开（公告）日：2022-07-06

  The present invention relates to a pharmaceutical composition for prevention or treatment of solid cancer comprising an epidithiodioxopiperazine derivative compound based on a parent structure comprising an intramolecular disulfide bridge in an epidithiodioxopiperazine ring or a pharmaceutically acceptable salt thereof as an active ingredient.

  本发明涉及一种用于预防或治疗实体瘤的药物组合物，该组合物包含一种基于母体结构的表二硫代二氧哌嗪衍生物化合物，该母体结构包含表二硫代二氧哌嗪环中的分子内二硫桥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。