Magreth-18a | 1315334-00-9

• 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: Magreth-18a
• 英文别名: 4-(2-pentoxy-5-prop-2-enylphenyl)-2-prop-2-enylphenol
• CAS: 1315334-00-9
• 化学式: C₂₃H₂₈O₂
• 分子量: 336.474
• InChiKey: ZYXPZNUJASUZOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  Magreth-18a 、 13-(5-iodopentyl)-9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium iodide 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成
  参考文献：
  名称：

  一种线粒体靶向化合物及其制备方法和应用

  摘要：

  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。

  公开号：

  CN111349092B
• 作为产物：
  描述：

  1-溴戊烷 、 和厚朴酚 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 3′,5-diallyl-4′-(pentyloxy)-[1,1′-biphenyl]-2-ol 、 Magreth-18a
  参考文献：
  名称：

  Mechanisms of Osteoclastogenesis Inhibition by a Novel Class of Biphenyl-Type Cannabinoid CB2 Receptor Inverse Agonists

  摘要：

  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.

  DOI：

  10.1016/j.chembiol.2011.05.012

文献信息

• [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。
• MITO-HONOKIOL COMPOUNDS AND METHODS OF SYNTHESIS AND USE THEREOF
  申请人：THE MEDICAL COLLEGE OF WISCONSIN, INC.

  公开号：US20180134737A1

  公开（公告）日：2018-05-17

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