(3S,6S)-3,6-bis((benzyloxy)methyl)piperazine-2,5-dione

• 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: (3S,6S)-3,6-bis((benzyloxy)methyl)piperazine-2,5-dione
• 英文别名: (3S,6S)-3,6-Bis((benzyloxy)methyl)piperazine-2,5-dione；(3S,6S)-3,6-bis(phenylmethoxymethyl)piperazine-2,5-dione
• 化学式: C₂₀H₂₂N₂O₄
• 分子量: 354.406
• InChiKey: DEEJCDRDHJVIGO-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,6S)-3,6-bis((benzyloxy)methyl)piperazine-2,5-dione 在 C₂₄H₂₀ClN₂OPRu 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 为溶剂， 110.0 ℃ 、4.05 MPa 条件下， 反应 48.0h， 以61%的产率得到O-benzyl-L-serinol
  参考文献：
  名称：

  在Ru催化下伯酰胺和环状二肽的选择性氢化。

  摘要：

  报道了钌（II）催化的具有挑战性的伯酰胺和环状二肽分别选择性氢化为其相应的伯醇和氨基醇。氢化反应在温和的生态友好条件下进行，并且可以扩大规模。

  DOI：

  10.1039/d0cc04550k
• 作为产物：
  描述：

  N-BOC-O-苄基-L-丝氨酸 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (3S,6S)-3,6-bis((benzyloxy)methyl)piperazine-2,5-dione
  参考文献：
  名称：

  Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens

  摘要：

  Microorganisms embedded in a biofilm are significantly more resistant to antimicrobial agents and the defences of the human immune system, than their planktonic counterpart. Consequently, compounds that can inhibit biofilm formation are of great interest for novel therapeutics. In this study, a screening approach was used to identify novel cyclic dipeptides that have anti-biofilm activity against oral pathogens. Five new active compounds were identified that prevent biofilm formation by the cariogenic bacterium Streptococcus mutans and the pathogenic fungus Candida albicans. These compounds also inhibit the adherence of microorganisms to a hydroxylapatite surface. Further investigations were conducted on these compounds to establish the structure-activity relationship, and it was deduced that the common cleft pattern is required for these molecules to act effectively against biofilms.

  DOI：

  10.1016/j.bmc.2018.11.042

文献信息

• Hydrophobic cyclic dipeptides as M⁺/Cl⁻carriers
  作者：Umatai A. Hale、Nandita Madhavan

  DOI：10.1039/d3cc02132g

  日期：——

  An interplay of ester and amide units for transmembrane KCl co-transport using simple cyclic dipeptides.

  利用简单的环状二肽实现跨膜 KCl 协同转运的酯和酰胺单元的相互作用。
• Interfacial supramolecular biomimetic epoxidation catalysed by cyclic dipeptides
  作者：Christopher Bérubé、Xavier Barbeau、Sébastien Cardinal、Pierre-Luc Boudreault、Corinne Bouchard、Nicolas Delcey、Patrick Lagüe、Normand Voyer

  DOI：10.1080/10610278.2016.1236197

  日期：2017.5.4

  We synthesised a library of cis- and trans-cyclic dipeptides and evaluated their efficacy as catalysts in the asymmetric Weitz-Scheffer epoxidation of trans-chalcone. A thorough investigation relying on structure-activity studies and computational studies provided insights into the mechanism of the process. Our results revealed some structural features required for efficient conversion and for introduction of chirality into the product. The cyclic dipeptide acts as a catalyst by templating a supramolecular arrangement at the aqueous-organic interface required for efficient transformations to occur. Among all cyclic dipeptides investigated, cyclo(Leu-Leu) was the most efficient supramolecular catalyst.[GRAPHICS].
• 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.