tetraethyl (6E,11E)-2,6,12,16-tetramethyl-2,6,11,15-heptadecenyl-9,9-bisphosphonate | 878143-01-2

• 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: tetraethyl (6E,11E)-2,6,12,16-tetramethyl-2,6,11,15-heptadecenyl-9,9-bisphosphonate
• 英文别名: tetraethyl 4,8-dimethyl-3,7-nonadienyl-1,1-bisphosphonate；Tetraethyl ((6E,11E)-2,6,12,16-tetramethylheptadeca-2,6,11,15-tetraene-9,9-diyl)bis(phosphonate)；(6E,11E)-9,9-bis(diethoxyphosphoryl)-2,6,12,16-tetramethylheptadeca-2,6,11,15-tetraene
• CAS: 878143-01-2
• 化学式: C₂₉H₅₄O₆P₂
• 分子量: 560.692
• InChiKey: UCDITMMFQMXODQ-GPAWKIAZSA-N

物化性质

• 沸点：
  615.5±55.0 °C(Predicted)
• 密度：
  1.010±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  37
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tetraethyl (6E,11E)-2,6,12,16-tetramethyl-2,6,11,15-heptadecenyl-9,9-bisphosphonate 在 2,3,5-三甲基吡啶 、 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 生成 digeranyl bisphosphonate
  参考文献：
  名称：

  Synthesis and biological activity of isoprenoid bisphosphonates

  摘要：

  Bisphosphonates have been used in the clinic to treat osteoporosis and to reduce bone resorption and the accompanying pathological bone fractures that attend a number of malignancies including multiple myeloma and cancers of the prostate, breast, and lung. There is also evidence that some bisphosphonates have direct anticancer activity. Expansion of the current class of bisphosphonates may lead to compounds that more selectively and potently target these cancers through inhibition of the mevalonate pathway. To this end, a set of dialkyl bisphosphonates bearing isoprenoid chains of varying lengths has been synthesized. Some of these compounds were found to have biological activity on post-translational processing of the oncogenic small GTPases, Ras and Rapla, in human-derived K562 leukemia cells. Most importantly, these compounds impair protein geranylgeranylation and not protein farnesylation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.010
• 作为产物：
  描述：

  香叶基溴 、 亚甲基二磷酸四乙酯 在 15-冠醚-5 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.67h， 以85%的产率得到tetraethyl (6E,11E)-2,6,12,16-tetramethyl-2,6,11,15-heptadecenyl-9,9-bisphosphonate
  参考文献：
  名称：

  Geranylgeranyl pyrophosphate synthase inhibitors

  摘要：

  这项发明提供了一种新型的焦磷酸合酶抑制剂，其化学式为I，以及包含这种抑制剂的组合物和使用它们的方法。

  公开号：

  US20060052347A1

文献信息

• Geranylgeranyl pyrophosphate synthase inhibitors
  申请人：Wiemer F. David

  公开号：US20060052347A1

  公开（公告）日：2006-03-09

  The invention provides novel pyrophosphate synthase inhibitors of formula I as well as compositions comprising such inhibitors and methods for their use.

  这项发明提供了一种新型的焦磷酸合酶抑制剂，其化学式为I，以及包含这种抑制剂的组合物和使用它们的方法。
• Synthesis and biological activity of isoprenoid bisphosphonates
  作者：Larry W. Shull、Andrew J. Wiemer、Raymond J. Hohl、David F. Wiemer

  DOI：10.1016/j.bmc.2006.02.010

  日期：2006.6

  Bisphosphonates have been used in the clinic to treat osteoporosis and to reduce bone resorption and the accompanying pathological bone fractures that attend a number of malignancies including multiple myeloma and cancers of the prostate, breast, and lung. There is also evidence that some bisphosphonates have direct anticancer activity. Expansion of the current class of bisphosphonates may lead to compounds that more selectively and potently target these cancers through inhibition of the mevalonate pathway. To this end, a set of dialkyl bisphosphonates bearing isoprenoid chains of varying lengths has been synthesized. Some of these compounds were found to have biological activity on post-translational processing of the oncogenic small GTPases, Ras and Rapla, in human-derived K562 leukemia cells. Most importantly, these compounds impair protein geranylgeranylation and not protein farnesylation. (c) 2006 Elsevier Ltd. All rights reserved.