3-甲酰化和厚朴酚 | 1008715-10-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-甲酰化和厚朴酚
• 英文名称: 3'-formylhonokiol
• 英文别名: 3-formylated honokiol；2-hydroxy-3-(4-hydroxy-3-prop-2-enylphenyl)-5-prop-2-enylbenzaldehyde
• CAS: 1008715-10-3
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: KABZVLVPWXZMFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-甲酰化和厚朴酚 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 以81.3%的产率得到3',5-diallyl-3-(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
• 作为产物：
  描述：

  氯仿 、 和厚朴酚 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 生成 3-甲酰化和厚朴酚 、 3,5'-diformylated honokiol
  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

• [EN] MITO-HONOKIOL COMPOUNDS AND METHODS OF SYNTHESIS AND USE THEREOF<br/>[FR] COMPOSÉS MITO-HONOKIOL ET LEURS PROCÉDÉS DE SYNTHÈSE ET D'UTILISATION
  申请人：MEDICAL COLLEGE WISCONSIN INC

  公开号：WO2016201188A1

  公开（公告）日：2016-12-15

  The present invention provides mito-honokiol compounds, pharmaceutical compositions thereof, and methods of using the mito-honokiol compounds in the treatment of cancer.

  本发明提供了mito-honokiol化合物、其药物组合物以及使用mito-honokiol化合物治疗癌症的方法。
• Mito-honokiol compounds and methods of synthesis and use thereof
  申请人：THE MEDICAL COLLEGE OF WISCONSIN, INC.

  公开号：US10836782B2

  公开（公告）日：2020-11-17

  The present invention provides mito-honokiol compounds, pharmaceutical compositions thereof, and methods of using the mito-honokiol compounds in the treatment of cancer.

  本发明提供了咪托-檀香醇化合物、其药物组合物以及使用咪托-檀香醇化合物治疗癌症的方法。
• Semi-synthesis and anti-proliferative activity evaluation of novel analogues of Honokiol
  作者：Youfu Luo、Yongbin Xu、Lijuan Chen、Jia Hu、Cheng Peng、DaChun Xie、Jianyou Shi、Wencai Huang、Guobin Xu、Ming Peng、Jing Han、Rui Li、Shengyong Yang、Yuquan Wei

  DOI：10.1016/j.bmcl.2009.06.071

  日期：2009.8

  A series of honokiol analogues were synthesized by modifying the 5- and/or 3'-position(s) of honokiol to assess their anti-tumor effects. Some compounds exerted more potent anti-proliferative activities than those of honokiol on K562 leukemia cells, A549 alveolar basal epithelial cells, SPC-A1 adenocarcinoma cells and A2780 human ovarian carcinoma cells in vitro. Compounds 2b, 3a, and 3c displayed most potent anti-proliferative activities against these tested cell strains and their anti-drug resistance effects were evaluated in vitro on cisplatin-resistant A2780 human ovarian carcinoma cells. The structure-activity relationship was also proposed. (C) 2009 Published by Elsevier Ltd.
• MITO-HONOKIOL COMPOUNDS AND METHODS OF SYNTHESIS AND USE THEREOF
  申请人：The Medical College of Wisconsin, Inc.

  公开号：EP3307254B1

  公开（公告）日：2020-08-05
• Mito-Honokiol Compounds and Methods of Synthesis and Use Thereof
  申请人：The Medical College of Wisconsin, Inc.

  公开号：US20210070787A1

  公开（公告）日：2021-03-11

  The present invention provides mito-honokiol or mito-magnolol compounds, pharmaceutical compositions thereof, and methods of using the mito-honokiol or mito-magnolol compounds in the treatment of cancer.