7-hydroxy-3-methoxycadalene | 36150-19-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 7-hydroxy-3-methoxycadalene
• 英文别名: cadalene；6-Methoxy-3,8-dimethyl-5-(propan-2-yl)naphthalen-2-ol；6-methoxy-3,8-dimethyl-5-propan-2-ylnaphthalen-2-ol
• CAS: 36150-19-3
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: XHYLUGWBNOECRE-UHFFFAOYSA-N

物化性质

• 沸点：
  399.1±30.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  7-hydroxy-3-methoxycadalene 、 2,3,4,6-四邻乙酰基-alpha-d-吡喃葡萄糖三氯乙酰胺 在 三氟化硼乙醚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以89%的产率得到tetra-acylated-β-Glc-O-cadalene
  参考文献：
  名称：

  Enhanced efficacy of 7-hydroxy-3-methoxycadalene via glycosylation in in vivo xenograft study

  摘要：

  7-Hydroxy-3-methoxycadalene, isolated from Zelkova serrata Makino, was confirmed as a biologically active natural compound. In this study, the efficacy of cadalene as an anticancer agent was tested. In order to address the poor physicochemical properties of cadalene, we designed and synthesized glycosylated cadalene derivatives for improved solubility and efficient drug delivery as a potential prodrug. In vitro cell viability assays confirmed that glycosylated cadalenes were less toxic and more soluble than cadalene. In an in vivo xenograft study in mice, the oral administration of glycosylated cadalenes caused a significant reduction in tumor size. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.08.071

文献信息

• Enhanced efficacy of 7-hydroxy-3-methoxycadalene via glycosylation in in vivo xenograft study
  作者：Hyang Yeon Lee、Jung-Taek Kwon、Minseob Koh、Myung-Haing Cho、Seung Bum Park

  DOI：10.1016/j.bmcl.2007.08.071

  日期：2007.11

  7-Hydroxy-3-methoxycadalene, isolated from Zelkova serrata Makino, was confirmed as a biologically active natural compound. In this study, the efficacy of cadalene as an anticancer agent was tested. In order to address the poor physicochemical properties of cadalene, we designed and synthesized glycosylated cadalene derivatives for improved solubility and efficient drug delivery as a potential prodrug. In vitro cell viability assays confirmed that glycosylated cadalenes were less toxic and more soluble than cadalene. In an in vivo xenograft study in mice, the oral administration of glycosylated cadalenes caused a significant reduction in tumor size. (C) 2007 Elsevier Ltd. All rights reserved.