methyl 2-[[(2E,7E)-5,5-bis(diethoxyphosphoryl)-2,8,12-trimethyltrideca-2,7,11-trienyl]amino]benzoate | 878143-09-0

• 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: methyl 2-[[(2E,7E)-5,5-bis(diethoxyphosphoryl)-2,8,12-trimethyltrideca-2,7,11-trienyl]amino]benzoate
• CAS: 878143-09-0
• 化学式: C₃₂H₅₃NO₈P₂
• 分子量: 641.722
• InChiKey: GMYSDIWBNDVYHH-GPAWKIAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  43
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2-[[(2E,7E)-5,5-bis(diethoxyphosphoryl)-2,8,12-trimethyltrideca-2,7,11-trienyl]amino]benzoate 在 2,4,6-三甲基吡啶 、 sodium hydroxide 、 三甲基溴硅烷 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Synthesis of fluorescently tagged isoprenoid bisphosphonates that inhibit protein geranylgeranylation

  摘要：

  Geminal bisphosphonates call be used for a variety of purposes in human disease including reduction of bone resorption in osteoporosis, treatment of fractures associated with malignancies of the prostate, breast, and lung, and direct anticancer activity against bone marrow derived malignancies. Previous research led to identification of some novel isoprenoid bisphosplionates that inhibit geranylgeranyl pyrophosphate (GGPP) synthesis and diminish protein geranylgeranylation. Described here is the synthesis of fluorescent anthranilate analogues of the most active isoprenoid bisphosphonates and examine their ability to impact post-translational processing of the small GTPases Ras, Rap I a, and Rab6. Similar to their non-fluorescent counterparts, some of these fluorescent isoprenoid bisphosphonates diminish protein geranylgeranylation. Their biological activity and fluorescent character suggest that they may be useful in studies of bisphosphonate localization both ill Cultured cells and in whole organisms. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.002
• 作为产物：
  描述：

  梨醇酯 在 叔丁基过氧化氢 、 manganese(IV) oxide 、 selenium(IV) oxide 、 15-冠醚-5 、 4 A molecular sieve 、 三乙酰氧基硼氢化钠 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 lithium bromide 、 对羟基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 57.5h， 生成 methyl 2-[[(2E,7E)-5,5-bis(diethoxyphosphoryl)-2,8,12-trimethyltrideca-2,7,11-trienyl]amino]benzoate
  参考文献：
  名称：

  Synthesis of fluorescently tagged isoprenoid bisphosphonates that inhibit protein geranylgeranylation

  摘要：

  Geminal bisphosphonates call be used for a variety of purposes in human disease including reduction of bone resorption in osteoporosis, treatment of fractures associated with malignancies of the prostate, breast, and lung, and direct anticancer activity against bone marrow derived malignancies. Previous research led to identification of some novel isoprenoid bisphosplionates that inhibit geranylgeranyl pyrophosphate (GGPP) synthesis and diminish protein geranylgeranylation. Described here is the synthesis of fluorescent anthranilate analogues of the most active isoprenoid bisphosphonates and examine their ability to impact post-translational processing of the small GTPases Ras, Rap I a, and Rab6. Similar to their non-fluorescent counterparts, some of these fluorescent isoprenoid bisphosphonates diminish protein geranylgeranylation. Their biological activity and fluorescent character suggest that they may be useful in studies of bisphosphonate localization both ill Cultured cells and in whole organisms. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.002

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。
• US7268124B2
  申请人：——

  公开号：US7268124B2

  公开（公告）日：2007-09-11
• Synthesis of fluorescently tagged isoprenoid bisphosphonates that inhibit protein geranylgeranylation
  作者：Mona A. Maalouf、Andrew J. Wiemer、Craig H. Kuder、Raymond J. Hohl、David F. Wiemer

  DOI：10.1016/j.bmc.2007.01.002

  日期：2007.3

  Geminal bisphosphonates call be used for a variety of purposes in human disease including reduction of bone resorption in osteoporosis, treatment of fractures associated with malignancies of the prostate, breast, and lung, and direct anticancer activity against bone marrow derived malignancies. Previous research led to identification of some novel isoprenoid bisphosplionates that inhibit geranylgeranyl pyrophosphate (GGPP) synthesis and diminish protein geranylgeranylation. Described here is the synthesis of fluorescent anthranilate analogues of the most active isoprenoid bisphosphonates and examine their ability to impact post-translational processing of the small GTPases Ras, Rap I a, and Rab6. Similar to their non-fluorescent counterparts, some of these fluorescent isoprenoid bisphosphonates diminish protein geranylgeranylation. Their biological activity and fluorescent character suggest that they may be useful in studies of bisphosphonate localization both ill Cultured cells and in whole organisms. (c) 2007 Elsevier Ltd. All rights reserved.