(3R,6R)-3-benzyl-6-(4-hydroxybenzyl)piperazine-2,5-dione | 1589549-23-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (3R,6R)-3-benzyl-6-(4-hydroxybenzyl)piperazine-2,5-dione
• 英文别名: cyclo(D-Tyr-D-Phe)；cyclo(D-Phe-D-Tyr)；cyclo(Phe-Tyr)；(3R,6R)-3-benzyl-6-[(4-hydroxyphenyl)methyl]piperazine-2,5-dione
• CAS: 1589549-23-4
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: GRWVBLRIPRGGPD-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  D-酪氨酸甲酯 、 D-苯丙氨酸甲酯 以84%的产率得到(3R,6R)-3-benzyl-6-(4-hydroxybenzyl)piperazine-2,5-dione
  参考文献：
  名称：

  Cyclo（D-Tyr-D-Phe）：一种来自芽孢杆菌属的新型抗菌，抗癌和抗氧化环二肽。N菌株与大戟昆虫病原线虫有关。

  摘要：

  首次从芽孢杆菌属（Bacillus sp。）发酵的改良营养肉汤的乙酸乙酯提取物中分离出一种新的微生物环二肽（二酮哌嗪）环（d- Tyr- d- Phe）。N菌株与大黄鼠病原线虫相关。该化合物的抗菌活性通过最小抑菌浓度和琼脂圆盘扩散法对医学上重要的细菌进行测定，并且该化合物对测试细菌具有显着的抗菌作用。对表皮葡萄球菌（1 µg / ml）的活性最高，其次是奇异变形杆菌（Proteus mirabilis）（2 µg / ml）。环（d- Tyr- d- Phe）对S的活性。表皮优于标准抗生素氯霉素。Cyclo（d- Tyr- d- Phe）记录了对A549细胞的显着抗肿瘤活性（IC 50值：10μM），该化合物对信号传导至100μM的正常成纤维细胞的因子无细胞毒性。Cyclo（d- Tyr- d- Phe）诱导了A549细胞凋亡的显着形态变化和DNA片段化。cr啶橙/溴化乙锭染色的细胞表明环（d-

  DOI：

  10.1002/psc.2594

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.
• Cyclo(<scp>d</scp>-Tyr-<scp>d</scp>-Phe): a new antibacterial, anticancer, and antioxidant cyclic dipeptide from<i>Bacillus</i>sp. N strain associated with a rhabditid entomopathogenic nematode
  作者：S. Nishanth Kumar、C. Dileep、C. Mohandas、Bala Nambisan、Jayaprakas Ca

  DOI：10.1002/psc.2594

  日期：2014.3

  A new microbial cyclic dipeptide (diketopiperazine), cyclo(d‐Tyr‐d‐Phe) was isolated for the first time from the ethyl acetate extract of fermented modified nutrient broth of Bacillus sp. N strain associated with rhabditid Entomopathogenic nematode. Antibacterial activity of the compound was determined by minimum inhibitory concentration and agar disc diffusion method against medically important bacteria

  首次从芽孢杆菌属（Bacillus sp。）发酵的改良营养肉汤的乙酸乙酯提取物中分离出一种新的微生物环二肽（二酮哌嗪）环（d- Tyr- d- Phe）。N菌株与大黄鼠病原线虫相关。该化合物的抗菌活性通过最小抑菌浓度和琼脂圆盘扩散法对医学上重要的细菌进行测定，并且该化合物对测试细菌具有显着的抗菌作用。对表皮葡萄球菌（1 µg / ml）的活性最高，其次是奇异变形杆菌（Proteus mirabilis）（2 µg / ml）。环（d- Tyr- d- Phe）对S的活性。表皮优于标准抗生素氯霉素。Cyclo（d- Tyr- d- Phe）记录了对A549细胞的显着抗肿瘤活性（IC 50值：10μM），该化合物对信号传导至100μM的正常成纤维细胞的因子无细胞毒性。Cyclo（d- Tyr- d- Phe）诱导了A549细胞凋亡的显着形态变化和DNA片段化。cr啶橙/溴化乙锭染色的细胞表明环（d-