(1R,4aR,7S,8aS,10aS)-N-(1-adamantylmethyl)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2H-phenanthrene-1-carboxamide | 864818-37-1

• 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: (1R,4aR,7S,8aS,10aS)-N-(1-adamantylmethyl)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2H-phenanthrene-1-carboxamide
• CAS: 864818-37-1
• 化学式: C₃₁H₄₇NO
• 分子量: 449.72
• InChiKey: PQFNGPLIFDHHQQ-PMFBIFCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-金刚烷甲胺 、 Acanthoic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以6.5 mg的产率得到(1R,4aR,7S,8aS,10aS)-N-(1-adamantylmethyl)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2H-phenanthrene-1-carboxamide
  参考文献：
  名称：

  Diterpenoid, Steroid, and Triterpenoid Agonists of Liver X Receptors from Diversified Terrestrial Plants and Marine Sources

  摘要：

  It has been demonstrated that liver X receptors (LXR) play a significant role in cholesterol homeostasis. Agonists of LXR are expected to increase cellular cholesterol efflux, lower LDL, and raise HDL levels. Screening of a natural product library of plant extracts using a LXR-SPA binding assay and bioassay-guided fractionation of a number of plant and marine gorgonian extracts led to the isolation of a number of active compounds. These included acanthoic acid (1) and alcohol (2), viperidone (3), polycarpol (4), rosacea acid (5), a cycloartane derivative (6), a new cycloartane analogue (7), betulinic acid (8), and gorgostane derivatives (9, 10, and 11). Of these compounds, 1, 4, and 11 exhibited potent binding affinity for a-receptor with IC50 values of 0.25, 0.12, and 0.07 mu M, respectively. Functionally they also showed strong coactivator association stimulation for LXR alpha receptor with EC50 values of 0.18, 0.03, and 0.05 mu M, respectively. They also exhibited 15-, 8-, and 13-fold induction of the a-receptor in a transactivation assay in HEK-293 cells, respectively. In general these compounds were selective for the LXR a-receptor over the beta-receptor in all assays and were much better stimulators of the a-receptor than the endogenous steroid ligands.

  DOI：

  10.1021/np050182g

文献信息

• Diterpenoid, Steroid, and Triterpenoid Agonists of Liver X Receptors from Diversified Terrestrial Plants and Marine Sources
  作者：Hiranthi Jayasuriya、Kithsiri B. Herath、John G. Ondeyka、Ziqiang Guan、Robert P. Borris、Suroojnauth Tiwari、Wil de Jong、Flor Chavez、Jeremy Moss、Dennis W. Stevenson、Hans T. Beck、Marc Slattery、Nelson Zamora、Marvin Schulman、Aisha Ali、Neelam Sharma、Karen MacNaul、Nancy Hayes、John G. Menke、Sheo B. Singh

  DOI：10.1021/np050182g

  日期：2005.8.1

  It has been demonstrated that liver X receptors (LXR) play a significant role in cholesterol homeostasis. Agonists of LXR are expected to increase cellular cholesterol efflux, lower LDL, and raise HDL levels. Screening of a natural product library of plant extracts using a LXR-SPA binding assay and bioassay-guided fractionation of a number of plant and marine gorgonian extracts led to the isolation of a number of active compounds. These included acanthoic acid (1) and alcohol (2), viperidone (3), polycarpol (4), rosacea acid (5), a cycloartane derivative (6), a new cycloartane analogue (7), betulinic acid (8), and gorgostane derivatives (9, 10, and 11). Of these compounds, 1, 4, and 11 exhibited potent binding affinity for a-receptor with IC50 values of 0.25, 0.12, and 0.07 mu M, respectively. Functionally they also showed strong coactivator association stimulation for LXR alpha receptor with EC50 values of 0.18, 0.03, and 0.05 mu M, respectively. They also exhibited 15-, 8-, and 13-fold induction of the a-receptor in a transactivation assay in HEK-293 cells, respectively. In general these compounds were selective for the LXR a-receptor over the beta-receptor in all assays and were much better stimulators of the a-receptor than the endogenous steroid ligands.