(3S)-3-methyl-5-[(1R,2S)-1,2,5,5-tetramethyl-2,3,4,6,7,8-hexahydronaphthalen-1-yl]pentan-1-ol | 94390-75-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3S)-3-methyl-5-[(1R,2S)-1,2,5,5-tetramethyl-2,3,4,6,7,8-hexahydronaphthalen-1-yl]pentan-1-ol
• CAS: 94390-75-7
• 化学式: C₂₀H₃₆O
• 分子量: 292.505
• InChiKey: WMHZFLWHXAUKJG-TWOQFEAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  13(S)-labdan-8α,15-diol 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到(3S)-3-methyl-5-[(1R,2S)-1,2,5,5-tetramethyl-2,3,4,6,7,8-hexahydronaphthalen-1-yl]pentan-1-ol
  参考文献：
  名称：

  Evaluation of labdane derivatives as potential anti-inflammatory agents

  摘要：

  In the present study, a series of labdane derivatives (2-9) were prepared from labdanediol (1) and their potential as anti-inflammatory agents were evaluated on lipopolysaccharide (LPS)-treated RAW 264.7 macrophages. All compounds were able to inhibit LPS-induced nitric oxide (NO), although compounds 1, 2, 5, 8 and 9 exhibited the most potent effects with a range of IC50 values of 5-15 mu M. Similarly to the inhibitory effects on NO release, these labdane derivatives also inhibited prostaglandin E-2 (PGE(2)) production. However, analysis of cell viability demonstrated that effects on NO release and (PGE(2)) production of compounds 1, 8 and 9 were due to citotoxicity, whereas compound 2 and 5 did not show any effect in the survival of RAW 264.7 macrophages. In addition to these in vitro data, compound 5 also showed anti-inflammatory activity in vivo, when tested in mice. They prevented the extent of swelling in the TPA-induced ear edema model and inhibited MPO activity, showing similar potency to that of the widely used anti-inflammatory drug indomethacin. These results indicate that compound 2 and in particular compound 5 might be used for the design of new anti-inflammatory agents. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.007

文献信息

• Evaluation of labdane derivatives as potential anti-inflammatory agents
  作者：Natalia Girón、Elisa Pérez-Sacau、Raquel López-Fontal、Juan M. Amaro-Luis、Sonsoles Hortelano、Ana Estevez-Braun、Beatriz de las Heras

  DOI：10.1016/j.ejmech.2010.04.007

  日期：2010.7

  In the present study, a series of labdane derivatives (2-9) were prepared from labdanediol (1) and their potential as anti-inflammatory agents were evaluated on lipopolysaccharide (LPS)-treated RAW 264.7 macrophages. All compounds were able to inhibit LPS-induced nitric oxide (NO), although compounds 1, 2, 5, 8 and 9 exhibited the most potent effects with a range of IC50 values of 5-15 mu M. Similarly to the inhibitory effects on NO release, these labdane derivatives also inhibited prostaglandin E-2 (PGE(2)) production. However, analysis of cell viability demonstrated that effects on NO release and (PGE(2)) production of compounds 1, 8 and 9 were due to citotoxicity, whereas compound 2 and 5 did not show any effect in the survival of RAW 264.7 macrophages. In addition to these in vitro data, compound 5 also showed anti-inflammatory activity in vivo, when tested in mice. They prevented the extent of swelling in the TPA-induced ear edema model and inhibited MPO activity, showing similar potency to that of the widely used anti-inflammatory drug indomethacin. These results indicate that compound 2 and in particular compound 5 might be used for the design of new anti-inflammatory agents. (C) 2010 Elsevier Masson SAS. All rights reserved.