6'-hydroxy-justicidin A | 145971-08-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 6'-hydroxy-justicidin A
• 英文别名: 6'-Hydroxyjusticidin A；9-(6-hydroxy-1,3-benzodioxol-5-yl)-4,6,7-trimethoxy-3H-benzo[f][2]benzofuran-1-one
• CAS: 145971-08-0
• 化学式: C₂₂H₁₈O₈
• 分子量: 410.38
• InChiKey: DFVZQTUMRRMHEL-UHFFFAOYSA-N

物化性质

• 熔点：
  218～220℃
• 沸点：
  681.1±55.0 °C(Predicted)
• 密度：
  1.429±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6'-hydroxy-justicidin A 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 以53.8%的产率得到1-[6'-(2",3",4",6"-tetra-O-acetyl-β-D-glucopyranosyloxy)-3',4'-benzodioxol-1'-yl]-4,6,7-trimethoxynaphtho[2,3-c]furan-11(3H)-one
  参考文献：
  名称：

  The synthesis of justicidinoside B and its atropisomer

  摘要：

  The first synthesis of justicidinoside B and its atropisomer was reported and their absolute configurations were determined by the CD exciton chirality method. The structures were confirmed by H-1 NMR, C-13 NMR, and HRMS.

  DOI：

  10.1080/10286020.2013.805208
• 作为产物：
  描述：

  6′-benzyloxydiphyllin 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 4.0h， 生成 6'-hydroxy-justicidin A
  参考文献：
  名称：

  全合成6'-羟基正义素A.

  摘要：

  已经完成了从Justicia procumbens L.分离的对癌细胞具有良好抑制活性的6'-羟基正义素A的第一次全合成。通过1 H NMR，13 C NMR和HR-ESI-MS确认结构。关键步骤涉及Diels-Alder环加成反应和NaBH 4的减少。

  DOI：

  10.1080/10286020.2011.653561

文献信息

• TRANSGLUTAMINASE ACTIVATOR
  申请人：Kao Corporation

  公开号：EP2918280A1

  公开（公告）日：2015-09-16

  A transglutaminase activator containing at least one kind selected from the group consisting of an extract from Justicia procumbens, an extract from Peristrophe japonica, and a compound represented by Formula (1), as an active ingredient: wherein R1 and R2 represent a hydrogen atom, a hydroxyl group, or an alkoxy group having 1 to 4 carbon atoms; R3 represents a hydrogen atom, or a group for forming a methylenedioxy group by bonding with R2; R4 and R5 represent a hydrogen atom, or a group for forming a methylenedioxy group by bonding with each other; R6 represents a hydrogen atom, a hydroxyl group, an alkoxy group having 1 to 5 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, or a specific sugar residue.

  一种转谷氨酰胺酶激活剂，其活性成分中至少含有一种从 Justicia procumbens 提取物、Peristrophe japonica 提取物和由式（1）代表的化合物组成的组中选出的物质： 其中 R1 和 R2 代表氢原子、羟基或具有 1 至 4 个碳原子的烷氧基；R3 代表氢原子或通过与 R2 键合形成亚甲二氧基的基团；R4 和 R5 代表氢原子或通过相互键合形成亚甲二氧基的基团；R6 代表氢原子、羟基、具有 1 至 5 个碳原子的烷氧基、具有 1 至 4 个碳原子的酰氧基或特定的糖残基。
• Transglutaminase Activator
  申请人：Kao Corporation

  公开号：US20150238404A1

  公开（公告）日：2015-08-27

  A transglutaminase activator containing at least one kind selected from the group consisting of an extract from Justicia procumbens , an extract from Peristrophe japonica , and a compound represented by Formula (1), as an active ingredient: wherein R 1 and R 2 represent a hydrogen atom, a hydroxyl group, or an alkoxy group having 1 to 4 carbon atoms; R 3 represents a hydrogen atom, or a group for forming a methylenedioxy group by bonding with R 2 ; R 4 and R 5 represent a hydrogen atom, or a group for forming a methylenedioxy group by bonding with each other; R 6 represents a hydrogen atom, a hydroxyl group, an alkoxy group having 1 to 5 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, or a specific sugar residue.
• Total synthesis of 6′-hydroxyjusticidin A
  作者：Lu Xiong、Ming-Gang Bi、Song Wu、Yuan-Feng Tong

  DOI：10.1080/10286020.2011.653561

  日期：2012.4

  The first total synthesis of 6′-hydroxyjusticidin A, isolated from Justicia procumbens L. with good inhibitory activity against cancer cells, has been accomplished. The structure was confirmed by 1H NMR, 13C NMR, and HR-ESI-MS. The key steps involved a Diels–Alder cycloaddition reaction and a reduction in NaBH4.

  已经完成了从Justicia procumbens L.分离的对癌细胞具有良好抑制活性的6'-羟基正义素A的第一次全合成。通过1 H NMR，13 C NMR和HR-ESI-MS确认结构。关键步骤涉及Diels-Alder环加成反应和NaBH 4的减少。
• The synthesis of justicidinoside B and its atropisomer
  作者：Sheng-Peng Wang、Yuan-Feng Tong、Li Li、Song Wu、Yan Qi

  DOI：10.1080/10286020.2013.805208

  日期：2013.6

  The first synthesis of justicidinoside B and its atropisomer was reported and their absolute configurations were determined by the CD exciton chirality method. The structures were confirmed by H-1 NMR, C-13 NMR, and HRMS.