m-prenyl-phenethylidene bisphosphonic acid tetraethyl ester | 1246189-21-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: m-prenyl-phenethylidene bisphosphonic acid tetraethyl ester
• 英文别名: 1-[2,2-Bis(diethoxyphosphoryl)ethyl]-3-(3-methylbut-2-enyl)benzene；1-[2,2-bis(diethoxyphosphoryl)ethyl]-3-(3-methylbut-2-enyl)benzene
• CAS: 1246189-21-8
• 化学式: C₂₁H₃₆O₆P₂
• 分子量: 446.461
• InChiKey: RKHIMPIJOXOKEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  m-prenyl-phenethylidene bisphosphonic acid tetraethyl ester 在 2,4,6-三甲基吡啶 、 三甲基溴硅烷 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到m-prenyl-phenethylidene bisphosphonic acid tetra sodium salt
  参考文献：
  名称：

  Prenylated Bisphosphonates as Anti-tuberculosis Agents

  摘要：

  该发明提供了治疗分枝杆菌感染的方法，以及使用公式I的化合物抑制分枝杆菌多萜焦磷酸合成的方法。该发明还提供了公式I的新化合物，以及其盐和前药。

  公开号：

  US20100240612A1
• 作为产物：
  描述：

  3-(3-methyl-2-butenyl)benzyl bromide 、 亚甲基二磷酸四乙酯 在 15-冠醚-5 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.5h， 以2.4 g的产率得到m-prenyl-phenethylidene bisphosphonic acid tetraethyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of a series of aromatic bisphosphonates

  摘要：

  Geminal bisphosphonates display varied biological activity depending on the nature of the substituents on the central carbon atom. For example, the nitrogenous bisphosphonates zoledronate and risedronate inhibit the enzyme farnesyl diphosphate synthase while digeranyl bisphosphonate has been shown to inhibit the enzyme geranylgeranyl diphosphate synthase. We now have synthesized isoprenoid bisphosphonates where an aromatic ring has been used to replace one of the isoprenoid olefins in an isoprenoid bisphosphonate and investigated the ability of these new compounds to impair protein geranylgeranylation within cells. Several of these new compounds are potent inhibitors of the enzyme geranylgeranyl diphosphate synthase. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.036

文献信息

• Prenylated Bisphosphonates as Anti-tuberculosis Agents
  申请人：Wiemer David F.

  公开号：US20100240612A1

  公开（公告）日：2010-09-23

  The invention provides methods to treat a mycobacterium infection and methods to inhibit mycobacterial polyprenyl pyrophosphate synthesis with a compound of formula I. The invention also provides novel compounds of formula I as well as salts and prodrugs thereof.

  该发明提供了治疗分枝杆菌感染的方法，以及使用公式I的化合物抑制分枝杆菌多萜焦磷酸合成的方法。该发明还提供了公式I的新化合物，以及其盐和前药。
• PRENYLATED BISPHOSPHONATES AS ANTI-TUBERCULOSIS AGENTS
  申请人：University of Iowa Research Foundation

  公开号：EP2408447A1

  公开（公告）日：2012-01-25
• [EN] PRENYLATED BISPHOSPHONATES AS ANTI-TUBERCULOSIS AGENTS<br/>[FR] BISPHOSPHONATES PRÉNYLÉS EN TANT QU'AGENTS ANTITUBERCULEUX
  申请人：UNIV IOWA RES FOUND

  公开号：WO2010108190A1

  公开（公告）日：2010-09-23

  The invention provides methods to treat a mycobacterium infection and methods to inhibit mycobacterial polyprenyl pyrophosphate synthesis with a compound of formula I. The invention also provides novel compounds of formula I as well as salts and prodrugs thereof.
• Synthesis and biological evaluation of a series of aromatic bisphosphonates
  作者：Rocky J. Barney、Brian M. Wasko、Amel Dudakovic、Raymond J. Hohl、David F. Wiemer

  DOI：10.1016/j.bmc.2010.08.036

  日期：2010.10.15

  Geminal bisphosphonates display varied biological activity depending on the nature of the substituents on the central carbon atom. For example, the nitrogenous bisphosphonates zoledronate and risedronate inhibit the enzyme farnesyl diphosphate synthase while digeranyl bisphosphonate has been shown to inhibit the enzyme geranylgeranyl diphosphate synthase. We now have synthesized isoprenoid bisphosphonates where an aromatic ring has been used to replace one of the isoprenoid olefins in an isoprenoid bisphosphonate and investigated the ability of these new compounds to impair protein geranylgeranylation within cells. Several of these new compounds are potent inhibitors of the enzyme geranylgeranyl diphosphate synthase. (C) 2010 Elsevier Ltd. All rights reserved.