(3S,6S)-3-benzyl-6-(benzyloxymethyl)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-benzyl-6-(benzyloxymethyl)piperazine-2,5-dione
• 英文别名: (3S,6S)-3-benzyl-6-(phenylmethoxymethyl)piperazine-2,5-dione
• 化学式: C₁₉H₂₀N₂O₃
• 分子量: 324.379
• InChiKey: FPYOAPSSJUUCKI-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,6S)-3-benzyl-6-(benzyloxymethyl)piperazine-2,5-dione 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Novel chiral N,N′-dimethyl-1,4-piperazines with metal binding abilities

  摘要：

  With the objective of developing novel chiral ligands, we report an efficient strategy to prepare chiral N,N-dimethyl-1,4-piperazines, six-member heterocyclic molecules that possess metal binding features. We prepared and characterized 18 piperazines, and evaluated their ability to complex different mono- and divalent metals, using a rapid picrate extraction technique. Some newly prepared diamine ligands were used in diethylzinc alkylation of aryl aldehydes. Yields increased significantly in the presence of the diamine ligands, though enantioselectivity was low. The results demonstrate the validity of the approach for preparing and identifying useful chiral diamine ligands. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.051
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 、 N-BOC-O-苄基-L-丝氨酸 在 三乙胺 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 乙酸乙酯 为溶剂， 反应 24.5h， 以58%的产率得到(3S,6S)-3-benzyl-6-(benzyloxymethyl)piperazine-2,5-dione
  参考文献：
  名称：

  含苯丙氨酸的环状二肽-分子量最低的基于未修饰蛋白原氨基酸的水凝胶化剂。

  摘要：

  基于蛋白氨基酸苯丙氨酸与丝氨酸，半胱氨酸，谷氨酸，组氨酸和赖氨酸结合的环状二肽（二酮哌嗪-DKPs）被描述为简单而引人注目的低分子量水凝胶化剂。所选DKP的共混物显示出显着的pH依赖特性，可作为易于调整的材料应用于药物输送。

  DOI：

  10.1039/c3cc44110e

文献信息

• Phenylalanine-containing cyclic dipeptides – the lowest molecular weight hydrogelators based on unmodified proteinogenic amino acids
  作者：Alexander J. Kleinsmann、Boris J. Nachtsheim

  DOI：10.1039/c3cc44110e

  日期：——

  Cyclic dipeptides (diketopiperazines - DKPs) that are based on the proteinogenic amino acid phenylalanine in combination with serine, cysteine, glutamate, histidine and lysine are described as simple and remarkable low molecular weight hydrogelators. Blends of selected DKPs show remarkable pH-dependent properties and can be applied as easy to tune materials in drug delivery.

  基于蛋白氨基酸苯丙氨酸与丝氨酸，半胱氨酸，谷氨酸，组氨酸和赖氨酸结合的环状二肽（二酮哌嗪-DKPs）被描述为简单而引人注目的低分子量水凝胶化剂。所选DKP的共混物显示出显着的pH依赖特性，可作为易于调整的材料应用于药物输送。
• 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].
• Novel chiral N,N′-dimethyl-1,4-piperazines with metal binding abilities
  作者：Christopher Bérubé、Sébastien Cardinal、Pierre-Luc Boudreault、Xavier Barbeau、Nicolas Delcey、Martin Giguère、Dave Gleeton、Normand Voyer

  DOI：10.1016/j.tet.2015.08.051

  日期：2015.10

  With the objective of developing novel chiral ligands, we report an efficient strategy to prepare chiral N,N-dimethyl-1,4-piperazines, six-member heterocyclic molecules that possess metal binding features. We prepared and characterized 18 piperazines, and evaluated their ability to complex different mono- and divalent metals, using a rapid picrate extraction technique. Some newly prepared diamine ligands were used in diethylzinc alkylation of aryl aldehydes. Yields increased significantly in the presence of the diamine ligands, though enantioselectivity was low. The results demonstrate the validity of the approach for preparing and identifying useful chiral diamine ligands. (C) 2015 Elsevier Ltd. All rights reserved.
• Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens
  作者：Gaëlle Simon、Christopher Bérubé、Normand Voyer、Daniel Grenier

  DOI：10.1016/j.bmc.2018.11.042

  日期：2019.6

  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.