methanesulfonic acid-(Z)-(5,9-dimethyl-4,8-decadienyl)-ester | 145573-07-5

• 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: methanesulfonic acid-(Z)-(5,9-dimethyl-4,8-decadienyl)-ester
• 英文别名: (E)-5,9-Dimethyl-4,8-decadien-1-ol, methanesulfonate ester；[(4E)-5,9-dimethyldeca-4,8-dienyl] methanesulfonate
• CAS: 145573-07-5
• 化学式: C₁₃H₂₄O₃S
• 分子量: 260.398
• InChiKey: KYEQZQBPFGAJRY-UKTHLTGXSA-N

物化性质

• 沸点：
  387.3±31.0 °C(Predicted)
• 密度：
  1.011±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  17.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methanesulfonic acid-(Z)-(5,9-dimethyl-4,8-decadienyl)-ester 在 sodium iodide 作用下， 生成 <(E)-5,9-Dimethyl-4,8-decadienyl>triphenylphosphonium iodide
  参考文献：
  名称：

  Squalene synthetase. Inhibition by an ammonium analogue of a carbocationic intermediate in the conversion of presqualene pyrophosphate to squalene

  摘要：

  DOI：

  10.1021/ja00389a106
• 作为产物：
  描述：

  ethyl (E)-5,9-dimethyl-4,8-decadienoate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 生成 methanesulfonic acid-(Z)-(5,9-dimethyl-4,8-decadienyl)-ester
  参考文献：
  名称：

  Squalene synthetase. Inhibition by an ammonium analogue of a carbocationic intermediate in the conversion of presqualene pyrophosphate to squalene

  摘要：

  DOI：

  10.1021/ja00389a106

文献信息

• Bishomoisoprenoid triazole bisphosphonates as inhibitors of geranylgeranyl diphosphate synthase
  作者：Veronica S. Wills、Joseph I. Metzger、Cheryl Allen、Michelle L. Varney、David F. Wiemer、Sarah A. Holstein

  DOI：10.1016/j.bmc.2017.02.066

  日期：2017.4

  Protein geranylgeranylation reactions are dependent on the availability of geranylgeranyl diphosphate (GGDP), which serves as the isoprenoid donor. Inhibition of GGDP synthase (GGDPS) is of interest from a drug development perspective as GGDPS inhibition results in impaired protein geranylgeranylation, which in multiple myeloma, disrupts monoclonal protein trafficking and induces apoptosis. We have recently reported a series of isoprenoid triazole bisphosphonates and have demonstrated that a 3:1 mixture of homogeranyl and homoneryl isomers potently, and in a synergistic manner, inhibits GGDPS. We now present the synthesis and biological evaluation of a novel series of bishomoisoprenoid triazoles which furthers our understanding of the structure-function relationship of this class. These studies demonstrate the importance of chain length and olefin stereochemistry on inhibitory activity. (C) 2017 Elsevier Ltd. All rights reserved.