(3S,6R,8S)-6-hydroxy-3,6,9-trimethyl-2-oxo-2,3,3α,4,5,6,6α,7,8,9β-decahydroazuleno[4,5-β]furan-8-yl (E)-3-(4-(methylthio)phenyl)acrylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (3S,6R,8S)-6-hydroxy-3,6,9-trimethyl-2-oxo-2,3,3α,4,5,6,6α,7,8,9β-decahydroazuleno[4,5-β]furan-8-yl (E)-3-(4-(methylthio)phenyl)acrylate
• 英文别名: [(3S,3aS,6R,8S,9bS)-6-hydroxy-3,6,9-trimethyl-2-oxo-3,3a,4,5,6a,7,8,9b-octahydroazuleno[4,5-b]furan-8-yl] (E)-3-(4-methylsulfanylphenyl)prop-2-enoate
• 化学式: C₂₅H₃₀O₅S
• 分子量: 442.576
• InChiKey: JEJAAVMRDDPJPJ-RDXOAVPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  98.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  山道年 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 12.67h， 生成 (3S,6R,8S)-6-hydroxy-3,6,9-trimethyl-2-oxo-2,3,3α,4,5,6,6α,7,8,9β-decahydroazuleno[4,5-β]furan-8-yl (E)-3-(4-(methylthio)phenyl)acrylate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of guaiane-type sesquiterpene lactone derivatives with respect to inhibiting NO production in lipopolysaccharide-induced RAW 264.7 macrophages

  摘要：

  A guaiane framework was scaffolded by photochemical rearrangement reactions using α-santonin 1 as a starting material. Then, using a series of reactions, we synthesized the guaiane-type sesquiterpene lactone 5 in high yield. The inhibitory activities of compound 5 and of a series of derivatives on nitric oxide (NO) release were evaluated in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. Compounds 6g, 7h, 7i, 7k and 8g, exhibited significant inhibitory effects on NO production, with IC50 values of 14.8, 22.3, 18.3, 17.4 and 7.0 μM, respectively. Their cytotoxicities were also estimated using an MTT assay. The structure-activity relationships of these compounds were also discussed.

  DOI：

  10.1016/j.ejmech.2014.06.043

文献信息

• Synthesis and structure–activity relationships of guaiane-type sesquiterpene lactone derivatives with respect to inhibiting NO production in lipopolysaccharide-induced RAW 264.7 macrophages
  作者：Hao Chen、Bing-Yang Chen、Chun-Ting Liu、Zeng Zhao、Wen-Hao Shao、Hu Yuan、Kai-Jian Bi、Jiang-Yun Liu、Qing-Yan Sun、Wei-Dong Zhang

  DOI：10.1016/j.ejmech.2014.06.043

  日期：2014.8

  A guaiane framework was scaffolded by photochemical rearrangement reactions using α-santonin 1 as a starting material. Then, using a series of reactions, we synthesized the guaiane-type sesquiterpene lactone 5 in high yield. The inhibitory activities of compound 5 and of a series of derivatives on nitric oxide (NO) release were evaluated in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. Compounds 6g, 7h, 7i, 7k and 8g, exhibited significant inhibitory effects on NO production, with IC50 values of 14.8, 22.3, 18.3, 17.4 and 7.0 μM, respectively. Their cytotoxicities were also estimated using an MTT assay. The structure-activity relationships of these compounds were also discussed.