2-desoxy-4-epi-pulchellin

• 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: 2-desoxy-4-epi-pulchellin
• 英文别名: (3aS,5R,5aS,8S,8aS,9aR)-8-hydroxy-5,8a-dimethyl-1-methylidene-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-2-one
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: BOPADYWRUULRBD-MBICNOSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-desoxy-4-epi-pulchellin 在 硫酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 0.17h， 生成 (1R,3aS,5R,5aS,8S,8aS,9aR)-8-hydroxy-1-[[2-hydroxyethyl(methyl)amino]methyl]-5,8a-dimethyl-1,3a,4,5,5a,6,7,8,9,9a-decahydroazuleno[6,5-b]furan-2-one;sulfuric acid
  参考文献：
  名称：

  Synthetic derivatives of the natural product 13-amino 2-desoxy-4-epi-pulchellin inhibit STAT3 signaling and induce G2/M arrest and death of colon cancer cells

  摘要：

  2-Desoxy-4-epi-puchellin (PCL) is a sesquiterpene-lactone, which naturally occurs in many traditional Chinese medicinal plants, and has antitumor and anti-inflammatory activities. In this work, a series of 13-amino derivatives of PCL were synthesized through Michael addition reaction. Inhibition of IL-6-induced STAT3 signaling pathway and in vitro cytotoxicity of these compounds were evaluated, and their effect on the cell cycle was also studied. The methyl hydroxyethylamine derivatives showed higher potency than PCL, which could induce significant mitotic arrest via G2/M arrest in HCT116 cancer cells, indicating that these derivatives have the potential to be developed into anti-colon cancer drugs.

  DOI：

  10.1016/j.bmcl.2019.01.030

文献信息

• Eremophilanolides, eudesmanolides, guaianolides and other constituents from Ondetia linearis
  作者：C. Zdero、F. Bohlmann

  DOI：10.1016/s0031-9422(00)97819-1

  日期：1989.1

  Abstract The aerial parts of Ondetia linearis afforded in addition to known compounds, 13 eremophilanolides, six eudesmanolides, one pseudoguaianolide and two norsesquiterpenes. The structures were elucidated by high field NMR techniques. The chemotaxonomic aspects are discussed briefly.

  摘要 Ondetia linearis 的地上部分除了已知化合物外，还提供 13 种 eremophilanolides、6 种eu​​desmanoides、1 种假愈创木酚内酯和两种去甲半萜。通过高场核磁共振技术阐明了结构。简要讨论了化学分类学方面。
• ZDERO, C.;BOHLMANN, F., PHYTOCHEMISTRY, 28,(1989) N, C. 1653-1660
  作者：ZDERO, C.、BOHLMANN, F.

  DOI：——

  日期：——
• Synthetic derivatives of the natural product 13-amino 2-desoxy-4-epi-pulchellin inhibit STAT3 signaling and induce G2/M arrest and death of colon cancer cells
  作者：Junxing Niu、Hui Huang、Fei Wang、Xianjing Zhang、Yi Liu、Qiang Yu、Lihong Hu

  DOI：10.1016/j.bmcl.2019.01.030

  日期：2019.3

  2-Desoxy-4-epi-puchellin (PCL) is a sesquiterpene-lactone, which naturally occurs in many traditional Chinese medicinal plants, and has antitumor and anti-inflammatory activities. In this work, a series of 13-amino derivatives of PCL were synthesized through Michael addition reaction. Inhibition of IL-6-induced STAT3 signaling pathway and in vitro cytotoxicity of these compounds were evaluated, and their effect on the cell cycle was also studied. The methyl hydroxyethylamine derivatives showed higher potency than PCL, which could induce significant mitotic arrest via G2/M arrest in HCT116 cancer cells, indicating that these derivatives have the potential to be developed into anti-colon cancer drugs.