ent-11α,15α-Dihydroxykaur-16-en-19-oic acid | 57719-76-3

• 物质功能分类: 天然产物 - 萜类
• 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: ent-11α,15α-Dihydroxykaur-16-en-19-oic acid
• 英文别名: (1R,4S,5R,9R,10S,11S,13S,15R)-11,15-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• CAS: 57719-76-3
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: VRVOLALMVUEAHP-OBUMVCGPSA-N

物化性质

• 沸点：
  512.6±50.0 °C(Predicted)
• 密度：
  0.982 g/cm3
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

制备方法与用途

(4α,11β,15β)-11,15-二羟基kaur-16-en-19-oic酸是从突尼斯拉氏肺孢子虫(Pulicaria laciniata)中分离出来的一种化合物，该植物由Thell公司提供。鲜花【1】。

反应信息

• 作为反应物：
  描述：

  ent-11α,15α-Dihydroxykaur-16-en-19-oic acid 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 N-(phenyl)-N-(11β,15β-dihydroxykaur-16-ene-4α-yl)urea
  参考文献：
  名称：

  Discovery and structure–activity relationships of ent-Kaurene diterpenoids as potent and selective 11β-HSD1 inhibitors: Potential impact in diabetes

  摘要：

  The biological screening of a collection of nature occurring diterpenoids against 11 beta-HSD1 resulted in the discovery of the lead compound 1b, which pointed to the therapeutic potential for type 2 diabetes. Subsequently, an optimization project was initiated. Starting from compound 1b and its counterpart 2, the hemi-synthesis was performed on kaurenic acid scaffolds yielding 36 derivatives. Further evaluations on both human and mouse 11 beta-HSD revealed that seven urea derivatives exhibited significant improved potency and selectivity. Especially, the urea 19a has an IC50 (human 11 beta-HSD1) = 9.4 nM and selectivity index (human 11 beta-HSD) > 10,649. The 2D and 3D binding models of the complex 19a/11 beta-HSD1 were generated using docking simulations. Based on the results, the structural activity relationships (SARs) of compounds 1b and 2 were also discussed. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.010

文献信息

• Kaurane-type diterpenes from Adenostemma lavenia O. Kuntze.
  作者：Shigeru SHIMIZU、Toshio MIYASE、Kaoru UMEHARA、Akira UENO

  DOI：10.1248/cpb.38.1308

  日期：——

  Ten 11-oxygenated kauran-19-oic acids, ent-11α, 15α-dihydroxykaur-16-en-19-oic acid, ent-11α-hydroxy-15α-acetoxykaur-16-en-19-oic acid, ent-11α-hydroxy-15-oxo-kaur-16-en-19-oic acid and adenostemmoic acids A-G and their nine glycosides, paniculosides II and III and adenostemmosides A-G were characterized from Adenostemma lavenia O. KUNTZE. ent-11α-Hydroxy-15-oxo-kaur-16-en-19-oic acid and adenostemmoic acid B showed cytotoxic activity against L-5178Y cultured cell and prolonged the survival of mice.