3,5′-diallyl-2′-propoxy-[1,1′-biphenyl]-4-ol | 1315333-97-1

• 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-2′-propoxy-[1,1′-biphenyl]-4-ol
• 英文别名: 3,5'-diallyl-2'-propoxybiphenyl-4-ol；Magreth-17a；2-prop-2-enyl-4-(5-prop-2-enyl-2-propoxyphenyl)phenol
• CAS: 1315333-97-1
• 化学式: C₂₁H₂₄O₂
• 分子量: 308.42
• InChiKey: CPNPKRREQMIDHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5′-diallyl-2′-propoxy-[1,1′-biphenyl]-4-ol 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 65.0h， 生成 13-(2-(3-((3,5′-diallyl-2′-propoxy[1,1′-biphenyl]-4-yl)oxy)propoxy)-2-oxoethyl)-9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium bromide
  参考文献：
  名称：

  Mitochondrial targeting derivatives of honokiol enhanced selective antitumor activity in NCI-H446 cells and decreased in vivo toxicity in Caenorhabditis elegans

  摘要：

  DOI：

  10.1016/j.ejmech.2023.115996
• 作为产物：
  描述：

  和厚朴酚 、 1-碘代丙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以21%的产率得到3,5′-diallyl-2′-propoxy-[1,1′-biphenyl]-4-ol
  参考文献：
  名称：

  Anticancer Effects of Honokiol via Mitochondrial Dysfunction Are Strongly Enhanced by the Mitochondria-Targeting Carrier Berberine

  摘要：

  Mitochondrion is a favorable therapeutic target in cancer, given its regulation of bioenergetics and cell death. Honokiol exhibits antiproliferative effects through mitochondria-mediated death signaling. To enhance its anticancer potential and selectivity, we conjugated honokiol to berberine, a mitochondria-targeting carrier. All designed derivatives displayed 1 order of magnitude increased cytotoxicity compared with the parent compounds, especially with massive cytoplasmic vacuoles. Biological evaluation demonstrated the representative compound 6b localized within the mitochondria, and mitochondrial dilation resulted in vacuolization. 6b induced vacuolation-associated cell death and apoptosis with obvious mitochondrial dysfunction, as demonstrated by booming reactive oxygen species generation, opening mitochondrial permeability transition pore, and reducing mitochondrial membrane potential. The targeting property also conferred 6b with selectivity for tumor cells compared to normal cells. 6b inhibited cancer cell proliferation in the zebrafish xenograft model. These results demonstrate that berberine-linked honokiol derivatives open up a direction for novel mitochondrial-targeting antitumor agents.

  DOI：

  10.1021/acs.jmedchem.0c00881

文献信息

• 一种线粒体靶向化合物及其制备方法和应用
  申请人：山东大学

  公开号：CN111349092B

  公开（公告）日：2021-03-12

  本发明提供一种线粒体靶向化合物及其制备方法和应用，所述线粒体靶向化合物的结构如式I或式II所示：其中，R1与R2各自独立地选自氢原子或烷基取代基，烷基是指C1‑C5直链或支链的饱和烷基；n选自1‑18之间的整数；X‑选自卤素离子。该化合物能够特异性靶向线粒体，具有较好的抗肿瘤活性。
• [EN] MITOCHONDRIA TARGETING COMPOUND, PREPARATION METHOD THEREFOR AND USE THEREOF<br/>[FR] COMPOSÉ DE CIBLAGE DE MITOCHONDRIES, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION<br/>[ZH] 一种线粒体靶向化合物及其制备方法和应用
  申请人：UNIV SHANDONG

  公开号：WO2021212691A1

  公开（公告）日：2021-10-28

  一种线粒体靶向化合物及其制备方法和应用，所述线粒体靶向化合物的结构如式I或式II所示，其中，R 1与R 2各自独立地选自氢原子或烷基取代基，烷基是指C 1-C 5直链或支链的饱和烷基；n选自1-18之间的整数；X -选自卤素离子。该化合物能够特异性靶向线粒体，具有较好的抗肿瘤活性。
• 一种线粒体靶向和厚朴酚衍生物及其制备方法和应用
  申请人：山东大学

  公开号：CN116947817A

  公开（公告）日：2023-10-27

  本发明属于化学医药技术领域，具体涉及一种线粒体靶向和厚朴酚衍生物及其制备方法和应用。其为式I或式II所示化合物，或为式I或式II所示化合物的药学上可接受的盐，或为式I或式II所示化合物的药学上可接受的酯，或为式I或式II所示化合物的药学上可接受的溶剂化物；#imgabs0#其中，R1为C1～C5直链或支链的饱和烷基，R2为C1～C5直链或支链的饱和烷基，n为1～10的整数。本发明提供的线粒体靶向和厚朴酚衍生物不仅能够具有更高的抗肿瘤活性和细胞选择性，而且能够改善对秀丽隐杆线虫模型的体内毒性。
• 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.
• Mechanisms of Osteoclastogenesis Inhibition by a Novel Class of Biphenyl-Type Cannabinoid CB2 Receptor Inverse Agonists
  作者：Wolfgang Schuehly、Juan Manuel Viveros Paredes、Jonas Kleyer、Antje Huefner、Sharon Anavi-Goffer、Stefan Raduner、Karl-Heinz Altmann、Jürg Gertsch

  DOI：10.1016/j.chembiol.2011.05.012

  日期：2011.8

  The cannabinoid CB2 receptor is known to modulate osteoclast function by poorly understood mechanisms. Here, we report that the natural biphenyl neolignan 4'-O-methylhonokiol (MH) is a CB2 receptor-selective antiosteoclastogenic lead structure (K-i < 50 nM). Intriguingly, MH triggers a simultaneous G(i) inverse agonist response and a strong CB2 receptor-dependent increase in intracellular calcium. The most active inverse agonists from a library of MH derivatives inhibited osteoclastogenesis in RANK ligand-stimulated RAW264.7 cells and primary human macrophages. Moreover, these ligands potently inhibited the osteoclastogenic action of endocannabinoids. Our data show that CB2 receptor-mediated cAMP formation, but not intracellular calcium, is crucially involved in the regulation of osteoclastogenesis, primarily by inhibiting macrophage chemotaxis and TNF-alpha expression. MH is an easily accessible CB2 receptor-selective scaffold that exhibits a novel type of functional heterogeneity.