cis-L-L-3,6-Bis-(4-benzyloxybenzyl)piperazine-2,5-dione | 374674-80-3

• 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: cis-L-L-3,6-Bis-(4-benzyloxybenzyl)piperazine-2,5-dione
• 英文别名: (3S,6S)-3,6-bis(p-(benzyloxy)benzyl)piperazine-2,5-dione；cyclo(L-Tyr-Bn-L-Tyr-Bn)；cyclodi(4-O-benzyl-L-tyrosine)；cyclo[L-Tyr(OBn)-L-Tyr(OBn)]；(3S,6S)-3,6-bis[(4-phenylmethoxyphenyl)methyl]piperazine-2,5-dione
• CAS: 374674-80-3
• 化学式: C₃₂H₃₀N₂O₄
• 分子量: 506.601
• InChiKey: ZQWZOXZKTPYDHR-KYJUHHDHSA-N

物化性质

• 沸点：
  783.4±60.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  cis-L-L-3,6-Bis-(4-benzyloxybenzyl)piperazine-2,5-dione 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以77%的产率得到(2S,5S)-2,5-bis(4-(benzyloxy)benzyl)piperazine
  参考文献：
  名称：

  Herquline B 和 C 的全合成

  摘要：

  描述了 (-)-herquline B (2) 和迄今为止未识别的同源物 (+)-herquline C (3) 的全合成。合成分别需要 14 和 13 个步骤，并具有关键的恶唑啉还原，为哌嗪构建奠定了基础。

  DOI：

  10.1021/jacs.8b10212
• 作为产物：
  描述：

  Boc-O-苄基-L-酪氨酸 在 甲酸 、 N,N-二异丙基乙胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 生成 cis-L-L-3,6-Bis-(4-benzyloxybenzyl)piperazine-2,5-dione
  参考文献：
  名称：

  Synthesis of a reported calpain inhibitor isolated from Streptomyces griseus

  摘要：

  The reported diketopiperazine calpain inhibitor, cis-L-L-3.6-bis-(4-hydroxybenzyl)-1,4-dimethylpiperazine-2,5-dione 1, and its analogues 3 and 4 were synthesized from the corresponding amino acids. The previously assigned structure of 1 is confirmed but neither synthetic 1 nor its N-methylphenylalanine analogues 3 and 4 inhibit porcine erythrocyte calpain I. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00524-8

文献信息

• Synthesis of a small library of diketopiperazines as potential inhibitors of calpain
  作者：Yibin Zeng、Qingshan Li、Robert P. Hanzlik、Jeffrey Aubé

  DOI：10.1016/j.bmcl.2005.04.031

  日期：2005.6

  based on previously reported calpain inhibitors was synthesized. In addition, a concise total synthesis of the structurally related natural product phevalin (2) was accomplished. Despite literature reports that some of the compounds prepared were calpain inhibitors, none of the library members were found to have significant activity against recombinant human calpain I.

  合成了一个基于先前报道的钙蛋白酶抑制剂的2,5-二酮哌嗪小文库。此外，完成了与结构相关的天然产物phevalin（2）的简明全合成。尽管有文献报道所制备的某些化合物是钙蛋白酶抑制剂，但未发现任何文库成员对重组人钙蛋白酶I具有显着活性。
• Total Synthesis of Herquline B and C
  作者：Joshua B. Cox、Aoi Kimishima、John L. Wood

  DOI：10.1021/jacs.8b10212

  日期：2019.1.9

  The total syntheses of (-)-herquline B (2) and a heretofore-unrecognized congener, (+)-herquline C (3), are described. The syntheses require 14 and 13 steps, respectively, and feature a key oxazoline reduction that sets the stage for piperazine construction.

  描述了 (-)-herquline B (2) 和迄今为止未识别的同源物 (+)-herquline C (3) 的全合成。合成分别需要 14 和 13 个步骤，并具有关键的恶唑啉还原，为哌嗪构建奠定了基础。
• Homologous NRPS-like Gene Clusters Mediate Redundant Small-Molecule Biosynthesis in<i>Aspergillus flavus</i>
  作者：Ry R. Forseth、Saori Amaike、Daniel Schwenk、Katharyn J. Affeldt、Dirk Hoffmeister、Frank C. Schroeder、Nancy P. Keller

  DOI：10.1002/anie.201207456

  日期：2013.1.28

  Biosynthetic crosstalk: Most gene clusters in fungi are orphans with no known associated metabolites. NMR‐based comparative metabolomics was used to identify the products of two highly homologous orphan clusters in Aspergillus flavus. The two clusters encode partially redundant biosynthetic pathways that produce overlapping sets of novel fungal alkaloids, feature NRPS‐like genes with unusual functions,

  生物合成串扰：真菌中的大多数基因簇都是孤立的，没有已知的相关代谢物。基于 NMR 的比较代谢组学用于鉴定黄曲霉中两个高度同源的孤儿簇的产物。这两个簇编码部分冗余的生物合成途径，这些途径产生重叠的新型真菌生物碱组，具有具有不同寻常功能的 NRPS 样基因，并调节真菌发育。
• 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.
• Synthesis of a reported calpain inhibitor isolated from Streptomyces griseus
  作者：I.O Donkor、M.Lee Sanders

  DOI：10.1016/s0960-894x(01)00524-8

  日期：2001.10

  The reported diketopiperazine calpain inhibitor, cis-L-L-3.6-bis-(4-hydroxybenzyl)-1,4-dimethylpiperazine-2,5-dione 1, and its analogues 3 and 4 were synthesized from the corresponding amino acids. The previously assigned structure of 1 is confirmed but neither synthetic 1 nor its N-methylphenylalanine analogues 3 and 4 inhibit porcine erythrocyte calpain I. (C) 2001 Elsevier Science Ltd. All rights reserved.