3',5-diallyl-3,5'-bis(hydroxymethyl)biphenyl-2,4'-diol | 1333391-05-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3',5-diallyl-3,5'-bis(hydroxymethyl)biphenyl-2,4'-diol
• 英文别名: 2-[4-Hydroxy-3-(hydroxymethyl)-5-prop-2-enylphenyl]-6-(hydroxymethyl)-4-prop-2-enylphenol
• CAS: 1333391-05-1
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: WEXWHZSQIXHZSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  和厚朴酚 在 三乙酰氧基硼氢化钠 、 溶剂黄146 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 3',5-diallyl-3,5'-bis(hydroxymethyl)biphenyl-2,4'-diol
  参考文献：
  名称：

  Structural Modification of Honokiol, a Biphenyl Occurring in Magnolia officinalis: the Evaluation of Honokiol Analogues as Inhibitors of Angiogenesis and for Their Cytotoxicity and Structure–Activity Relationship

  摘要：

  Honokiol, widely known as an antitumor agent, has been used as an antiangiogenesis drug lead. In this paper, 47 honokiol analogues and derivatives were investigated for their antiangiogenic activity by application of the transgenic zebrafish screening model, antiproliferative and cytotoxic activity against HUVECs, and three tumor cell lines by MTT assay. 3',5-Diallyl-2, 4'-dihydroxy-[1,1'-biphen-yl]-3,5'-dicarbaldehyde (8c) was found to suppress the newly grown segmental vessels from the dorsal aorta of zebrafish and prevent inappropriate vascularization as well as exhibit more potent inhibitory effects on the proliferation of HUVECs, A549, HepG2, and LL/2 cells (IC50 = 15.1, 30.2, 10.7, and 21.7 mu M, respectively) than honokiol (IC50 = 52.6, 35.0, 16.5, and 65.4 mu M, respectively). Analogue 8c also effectively inhibited the migration and capillary-like tube formation of HUVECs in vitro. The antiangiogenic effect and antiproliferative activity of these structurally modified honokiol analogues and derivatives have led to the establishment of a structure-activity relationship.

  DOI：

  10.1021/jm200830u

文献信息

• Design, synthesis and antibacterial evaluation of honokiol derivatives
  作者：Bo Wu、Su-hong Fu、Huan Tang、Kai Chen、Qiang Zhang、Ai-Hua Peng、Hao-Yu Ye、Xing-Jun Cheng、Mao Lian、Zhen-ling Wang、Li-Juan Chen

  DOI：10.1016/j.bmcl.2017.06.022

  日期：2018.2

  pharmacologically active natural compound derived from the bark of Magnolia officinalis, has antibacterial activity against Staphylococcus aureus which provides a great inspiration for the discovery of potential antibacterial agents. Herein, honokiol derivatives were designed, synthesized and evaluated for their antibacterial activity by determining the minimum inhibitory concentration (MIC) against S. aureus

  金黄色葡萄球菌是一种主要的危险人类病原体，会引起一系列严重程度不同的临床表现，并且是皮肤和软组织感染，肺炎，化脓性关节炎，血管内感染，异物相关感染中最常见的病原体，败血病，骨髓炎和中毒性休克综合症。厚朴酚是一种从木兰皮中提取的具有药理活性的天然化合物，对金黄色葡萄球菌具有抗菌活性。这为发现潜在的抗菌剂提供了很大的启发。本文中，通过确定体外对金黄色葡萄球菌ATCC25923和大肠杆菌ATCC25922的最小抑制浓度（MIC）来设计，合成和评估厚朴酚衍生物的抗菌活性。7c表现出比其他衍生物和厚朴酚更好的抗菌活性。结构活性关系表明哌啶环与氨基基团有助于提高抗菌活性。此外，7c对多种细菌菌株（包括11种革兰氏阳性菌和7种革兰氏阴性菌）显示出广谱的抗菌效果。消灭时间的动力学金黄色葡萄球菌ATCC25923在体外显示，与相同浓度的利奈唑胺和万古霉素相比，7c表现出浓度依赖性作用和更快速的杀菌动力学。金
• Structural Modification of Honokiol, a Biphenyl Occurring in Magnolia officinalis: the Evaluation of Honokiol Analogues as Inhibitors of Angiogenesis and for Their Cytotoxicity and Structure–Activity Relationship
  作者：Liang Ma、Jinying Chen、Xuewei Wang、Xiaolin Liang、Youfu Luo、Wei Zhu、Tianen Wang、Ming Peng、Shucai Li、Shi Jie、Aihua Peng、Yuquan Wei、Lijuan Chen

  DOI：10.1021/jm200830u

  日期：2011.10.13

  Honokiol, widely known as an antitumor agent, has been used as an antiangiogenesis drug lead. In this paper, 47 honokiol analogues and derivatives were investigated for their antiangiogenic activity by application of the transgenic zebrafish screening model, antiproliferative and cytotoxic activity against HUVECs, and three tumor cell lines by MTT assay. 3',5-Diallyl-2, 4'-dihydroxy-[1,1'-biphen-yl]-3,5'-dicarbaldehyde (8c) was found to suppress the newly grown segmental vessels from the dorsal aorta of zebrafish and prevent inappropriate vascularization as well as exhibit more potent inhibitory effects on the proliferation of HUVECs, A549, HepG2, and LL/2 cells (IC50 = 15.1, 30.2, 10.7, and 21.7 mu M, respectively) than honokiol (IC50 = 52.6, 35.0, 16.5, and 65.4 mu M, respectively). Analogue 8c also effectively inhibited the migration and capillary-like tube formation of HUVECs in vitro. The antiangiogenic effect and antiproliferative activity of these structurally modified honokiol analogues and derivatives have led to the establishment of a structure-activity relationship.