1,4-dimethyl-2,5-diketopiperazine-3,6-dibromide | 21579-45-3

• 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-dimethyl-2,5-diketopiperazine-3,6-dibromide
• 英文别名: 1,4-dimethyl-2,5-piperazinedione-3,6-dibromide；3,6-Dibromo-1,4-dimethyl-2,5-piperazinedione；3,6-dibromo-1,4-dimethylpiperazine-2,5-dione；3,6-dibromosarcosine anhydride；3,6-dibromo-1,4-dimethyl-piperazine-2,5-dione；3,6-Dibrom-2,5-dioxo-1,4-dimethyl-piperazin
• CAS: 21579-45-3
• 化学式: C₆H₈Br₂N₂O₂
• 分子量: 299.95
• InChiKey: UHOBMCFQSYNXAE-UHFFFAOYSA-N

物化性质

• 熔点：
  139-143 °C
• 沸点：
  403.4±45.0 °C(Predicted)
• 密度：
  1.995±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-dimethyl-2,5-diketopiperazine-3,6-dibromide 在 硼烷四氢呋喃络合物 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 dragmacidin B
  参考文献：
  名称：

  德拉莫达菌素B的全合成

  摘要：

  描述了一种简单的德拉莫达菌素B的全合成。这构成了海洋生物碱的2,5-双（3'-吲哚基）哌嗪家族成员的首次合成。还制备了德拉莫达菌素B的双溴代类似物。

  DOI：

  10.1016/0040-4039(94)85056-9
• 作为产物：
  描述：

  肌氨酸酐 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 1,4-dimethyl-2,5-diketopiperazine-3,6-dibromide
  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

文献信息

• [EN] COMPOSITIONS AND METHODS FOR INHIBITING ACTIVITY OF HYPOXIA-INDUCIBLE TRANSCRIPTION FACTOR COMPLEX AND ITS USE FOR TREATMENT OF TUMORS<br/>[FR] COMPOSITIONS ET PROCÉDÉS D'INHIBITION DE L'ACTIVITÉ DU COMPLEXE DE FACTEUR DE TRANSCRIPTION INDUCTIBLE PAR L'HYPOXIE, ET UTILISATION DANS LE TRAITEMENT DE TUMEURS
  申请人：UNIV SOUTHERN CALIFORNIA

  公开号：WO2014035484A1

  公开（公告）日：2014-03-06

  Disclosed are epidithiodiketopiperazine compounds, pharmaceutical compositions based thereon and methods of treating, reducing or inhibiting transcription and translation of hypoxia-inducible genes. An embodiment of the present invention is directed to a method for interfering with hypoxia-induced transcriptional pathway. Generally, the method according to this embodiment comprises contacting a cell with at least one compound according to either Formula I, Formula II or Formula III, or a salt, solvent or hydrate thereof.

  揭示了一种二硫代二酮吡嗪化合物，基于该化合物的药物组合物以及治疗、减少或抑制缺氧诱导基因的转录和翻译的方法。本发明的一种实施例涉及干扰缺氧诱导的转录途径的方法。根据这种实施例的方法通常包括将细胞与根据化合物I、化合物II或化合物III中的至少一种，或其盐、溶剂或水合物进行接触。
• [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。
• [EN] EPIDITHIODIKETOPIPERAZINE COMPOUNDS, COMPOSITIONS, AND METHODS<br/>[FR] COMPOSÉS ÉPIDITHIODICÉTOPIPÉRAZINES, COMPOSITIONS ET PROCÉDÉS
  申请人：GLOBAVIR BIOSCIENCES INC

  公开号：WO2015095821A1

  公开（公告）日：2015-06-25

  Epidithiodiketopiperazine compounds, pharmaceutical compositions based thereon and methods of their synthesis, as part of treating, inhibiting and reducing transcription and translation of hypoxia inducible genes are described. In another aspect, the present disclosure describes a method for interfering with hypoxia-induced transcriptional pathway in a cell comprising: contacting the cell with at least one compound disclosed herein. In another aspect, the present disclosure describes a method for treating breast cancer, a solid cancer, a blood cancer, a subject suffering from carcinoma in need of said treatment, and renal cell carcinoma (RCC), comprising: administering to the subject an effective amount of at least one compound disclosed herein. In some embodiments of the methods described herein, the method further comprises administering an additional anti-cancer and/or cytotoxic agent.

  描述了Epidithiodiketopiperazine化合物、基于该化合物的药物组合物及其合成方法，作为治疗、抑制和减少低氧诱导基因的转录和翻译的一部分。在另一个方面，本公开说明描述了一种干扰细胞中低氧诱导转录途径的方法，包括：将细胞与至少一种本公开披露的化合物接触。在另一个方面，本公开说明描述了一种治疗乳腺癌、实体癌、血液癌、需要接受所述治疗的患有癌症的受试者以及肾细胞癌（RCC）的方法，包括：向受试者施用至少一种本公开披露的化合物的有效量。在所述方法的一些实施方式中，该方法还包括施用额外的抗癌和/或细胞毒药剂。
• Directing Bromination of Piperazine-2,5-diones
  作者：TW Badran、CLL Chai、CJ Easton、JB Harper、DM Page

  DOI：10.1071/ch9951379

  日期：——

  From intermolecular and intramolecular competition experiments, it has been established that, by comparison with an N-methyl substituent, an N-acetyl group deactivates glycine residues in piperazine-2,5-diones towards free-radical bromination. Combined with the ease of introduction and removal of N-acetyl substituents, the deactivating effect provides a method for regiocontrolled functionalization of these compounds.

  分子间和分子内竞争实验证明，与 N-甲基取代基相比，N-乙酰基能使哌嗪-2,5-二酮中的甘氨酸残基失去自由基溴化作用。由于 N-乙酰基取代基易于引入和去除，这种失活效果为这些化合物的区域控制官能化提供了一种方法。
• The Distal Effect of N-Electron-withdrawing Groups on the Stability of Peptide Carbon Radicals
  作者：Junming Ho、Michelle L. Coote、Christopher J. Easton

  DOI：10.1071/ch11003

  日期：——

  The effect of electron-withdrawing substituents, hydrogen bonding and protonation at amide nitrogen on the stability of radicals formed by loss of either a distal C–H adjacent to the amide carbonyl or one proximal to the amide nitrogen for a series of acetamides and diketopiperazines has been studied via high-level ab initio methods. These studies show that the effect is to destabilize the radicals formed by abstraction of the proximal hydrogens, typically by 10–20 kJ mol–1, and stabilize the distal radicals typically by 5–10 kJ mol–1, but only if the distal radicals are polarized by another dative substituent. The different radical stabilities are not directly mirrored in calculated activation energies or experimental rates of radical formation in bromination reactions, because there is significant charge development in these reaction transition states.

  通过高水平的 ab initio 方法，研究了酰胺和二酮哌嗪系列中，酰胺氮上的电子抽离取代基、氢键和质子化对酰胺羰基附近的远端 C-H 或酰胺氮近端 C-H 丢失所形成自由基稳定性的影响。这些研究表明，近端氢的抽取会使形成的自由基不稳定，通常会降低 10-20 kJ mol-1，而远端自由基通常会稳定 5-10 kJ mol-1，但前提是远端自由基被另一个二价取代基极化。不同的自由基稳定性并不能直接反映在溴化反应中自由基形成的计算活化能或实验速率中，因为这些反应过渡态中存在显著的电荷发展。