tetramethyl (E)-1,1-bis(4,8-dimethylnona-3,7-dienyl)-1,1-bisphosphonate

• 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: tetramethyl (E)-1,1-bis(4,8-dimethylnona-3,7-dienyl)-1,1-bisphosphonate
• 英文别名: tetramethyl (E)-1,1-bis(4,8-dimethyl-nona-3,7-dienyl)-1,1-bisphosphonate；(6E,11E)-9,9-bis(dimethoxyphosphoryl)-2,6,12,16-tetramethylheptadeca-2,6,11,15-tetraene
• 化学式: C₂₅H₄₆O₆P₂
• 分子量: 504.584
• InChiKey: PPSPGJDENIVHKB-GJHDBBOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  33
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  tetramethyl (E)-1,1-bis(4,8-dimethylnona-3,7-dienyl)-1,1-bisphosphonate 、 特戊酸氯甲酯 在 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以18%的产率得到tetrapivaloyloxymethyl (E)-1,1-bis(4,8-dimethyl-nona-3,7-dienyl)-1,1-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
• 作为产物：
  描述：

  香叶基溴 、 四甲基亚甲基二磷酸酯 在 15-冠醚-5 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.67h， 以15%的产率得到tetramethyl (E)-1,1-bis(4,8-dimethylnona-3,7-dienyl)-1,1-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

• Mono- and dialkyl isoprenoid bisphosphonates as geranylgeranyl diphosphate synthase inhibitors
  作者：Andrew J. Wiemer、Jose S. Yu、Kimberly M. Lamb、Raymond J. Hohl、David F. Wiemer

  DOI：10.1016/j.bmc.2007.09.029

  日期：2008.1

  Nitrogenous bisphosphonates are used clinically to reduce bone resorption associated with osteoporosis or metastatic bone disease, and are recognized as inhibitors of farnesyl diphosphate synthase. Inhibition of this enzyme decreases cellular levels of both farnesyl diphosphate and geranylgeranyl diphosphate which results in a variety of downstream biological effects including inhibition of protein geranylgeranylation. Our lab recently has prepared several isoprenoid bisphosphonates that inhibit protein geranylgeranylation and showed that one selectively inhibits geranylgeranyl diphosphate synthase. This results in depletion of intracellular geranylgeranyl diphosphate and impacts protein geranylgeranylation but does not affect protein farnesylation. To clarify the structural features of isoprenoid bisphosphonates that account for their geranylgeranyl diphosphate synthase inhibition, we have prepared a new group of isoprenoid bisphosphonates. The complete set of compounds has been tested for in vitro inhibition of human recombinant geranylgeranyl diphosphate synthase and cellular inhibition of protein geranylgeranylation. These results show some surprising relationships between in vitro and cellular activity, and will guide development of clinical agents directed at geranylgeranyl diphosphate synthase. (c) 2007 Elsevier Ltd. All rights reserved.
• GERANYLGERANYL PYROPHOSPHATE SYNTHASE INHIBITORS
  申请人：University of Iowa Research

  公开号：EP1793832B1

  公开（公告）日：2014-07-23
• US20140274967A1
  申请人：——

  公开号：US20140274967A1

  公开（公告）日：2014-09-18
• METHODS TO MODULATE RAC1 IMPORT AND TO TREAT PULMONARY FIBROSIS
  申请人：University of Iowa Research Foundation

  公开号：US20150005261A1

  公开（公告）日：2015-01-01

  The invention provides methods for treating fibrosis, as well as methods for modulating mitochondrial peroxide production in a cell, and methods for modulating the import of Rac1 into the mitochondria of a cell.
• US7268124B2
  申请人：——

  公开号：US7268124B2

  公开（公告）日：2007-09-11