(3S)-3,6-bis(p-(benzyloxy)benzyl)piperazine-2,5-dione | 1426060-09-4

• 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)-3,6-bis(p-(benzyloxy)benzyl)piperazine-2,5-dione
• 英文别名: (3R,6S)-3,6-bis[(4-phenylmethoxyphenyl)methyl]piperazine-2,5-dione
• CAS: 1426060-09-4
• 化学式: C₃₂H₃₀N₂O₄
• 分子量: 506.601
• InChiKey: ZQWZOXZKTPYDHR-RNPORBBMSA-N

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：

  (3S)-3,6-bis(p-(benzyloxy)benzyl)piperazine-2,5-dione 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以77%的产率得到(2S,5R)-2,5-bis(4-(benzyloxy)benzyl)piperazine
  参考文献：
  名称：

  同源NRPS样基因簇介导黄曲霉冗余小分子生物合成

  摘要：

  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。

  DOI：

  10.1002/anie.201207456
• 作为产物：
  描述：

  在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到(3S)-3,6-bis(p-(benzyloxy)benzyl)piperazine-2,5-dione
  参考文献：
  名称：

  同源NRPS样基因簇介导黄曲霉冗余小分子生物合成

  摘要：

  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。

  DOI：

  10.1002/anie.201207456

文献信息

• 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.
• Preventing Candida albicans biofilm formation using aromatic-rich piperazines
  作者：Gaëlle Simon、Christopher Bérubé、Pierre-Alexandre Paquet-Côté、Daniel Grenier、Normand Voyer

  DOI：10.1016/j.bmc.2020.115810

  日期：2020.12

  The global increase in microbial resistance is an imminent threat to public health. Effective treatment of infectious diseases now requires new antimicrobial therapies. We report herein the discovery of aromatic-rich piperazines that inhibit biofilm formation by C. albicans. 22 piperazines, including 16 novel ones, were prepared efficiently using a combination of solid- and solution phase synthesis. The most potent compound prevents morphological switching under several hypha-inducing conditions and reduces C. albicans' ability to adhere to epithelial cells. These processes are essential to the development of Candida biofilms, which are associated with its increased resistance to immune defenses and antifungal agents.
• 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。