dimethyl (6R)-6-hydroxy-3,7,7-trimethyloct-2-enedioate | 845734-45-4

• 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: dimethyl (6R)-6-hydroxy-3,7,7-trimethyloct-2-enedioate
• CAS: 845734-45-4
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: XIRDIDNBDLWNTK-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl (6R)-6-hydroxy-3,7,7-trimethyloct-2-enedioate 、 2,2-二甲氧基丙烷 在 titanium(IV) isopropylate 、 lithium aluminium tetrahydride 、 D-(-)-酒石酸二乙酯 、 叔丁醇 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 {(2R,3R)-3-Methyl-3-[2-((R)-2,2,5,5-tetramethyl-[1,3]dioxan-4-yl)-ethyl]-oxiranyl}-methanol
  参考文献：
  名称：

  The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function

  摘要：

  Tonantzitlolone A, a diterpene isolated from the Mexican plant Stillingia sanguinolenta, shows cytostatic activity. Both the natural product tonantzitlolone A and its synthetic enantiomer induce monoastral spindle formation in cell experiments which indicates inhibitory activity on kinesin-5 mitotic motor molecules. These inhibitory effects on kinesin-5 could be verified in in vitro single-molecule motility assays, where both tonantzitlolones interfered with kinesin-5 binding to its cellular interaction partner microtubules in a concentration-dependent manner, yet with a larger effect of the synthetic enantiomer. In contrast to kinesin-5 inhibition, both tonantzitlolone A enantiomers did not affect conventional kinesin-1 function; hence tonantzitlolones are not unspecific kinesin inhibitors. The observed stronger inhibitory effect of the synthetic enantiomer demonstrates the possibility to enhance the overall moderate anti-proliferative effect of the lead compound tonantzitlolon A by chemical modification. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.02.022

文献信息

• The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function
  作者：Tobias J. Pfeffer、Florenz Sasse、Christoph F. Schmidt、Stefan Lakämper、Andreas Kirschning、Tim Scholz

  DOI：10.1016/j.ejmech.2016.02.022

  日期：2016.4

  Tonantzitlolone A, a diterpene isolated from the Mexican plant Stillingia sanguinolenta, shows cytostatic activity. Both the natural product tonantzitlolone A and its synthetic enantiomer induce monoastral spindle formation in cell experiments which indicates inhibitory activity on kinesin-5 mitotic motor molecules. These inhibitory effects on kinesin-5 could be verified in in vitro single-molecule motility assays, where both tonantzitlolones interfered with kinesin-5 binding to its cellular interaction partner microtubules in a concentration-dependent manner, yet with a larger effect of the synthetic enantiomer. In contrast to kinesin-5 inhibition, both tonantzitlolone A enantiomers did not affect conventional kinesin-1 function; hence tonantzitlolones are not unspecific kinesin inhibitors. The observed stronger inhibitory effect of the synthetic enantiomer demonstrates the possibility to enhance the overall moderate anti-proliferative effect of the lead compound tonantzitlolon A by chemical modification. (C) 2016 Elsevier Masson SAS. All rights reserved.