(E)-4-hydroxy-3-methylbut-2-enyl methylenediphosphonate

• 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: (E)-4-hydroxy-3-methylbut-2-enyl methylenediphosphonate
• 英文别名: (E)-((hydroxy((4-hydroxy-3-methylbut-2-en-1-yl)oxy)phosphoryl)methyl)phosphonic acid；[hydroxy-[(E)-4-hydroxy-3-methylbut-2-enoxy]phosphoryl]methylphosphonic acid
• 化学式: C₆H₁₄O₇P₂
• 分子量: 260.12
• InChiKey: MWPLXVJYALXWPR-QHHAFSJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (E)-4-(t-butyldimethylsilyloxy)-3-methyl-but-2-enyl bromide 在 四丁基氟化铵 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 (E)-4-hydroxy-3-methylbut-2-enyl methylenediphosphonate
  参考文献：
  名称：

  Replacing the pyrophosphate group of HMB-PP by a diphosphonate function abrogates Its potential to activate human γδ T cells but does not lead to competitive antagonism

  摘要：

  The immunological characterization of (E)-4-hydroxy-3-methyl-but-2-enyl pyrophosphate (HMB-PP), and its methylenediphosphonate analogue, HMB-PCP, is described. With an EC50 of 0.1-0.2 nM, HMB-PP is significantly more potent in stimulating human Vgamma9/Vdelta2 T cells than any other compound described so far. However, replacing the pyrophosphate by a P-CH2-P function abrogates the bioactivity drastically, with HMB-PCP having a EC50 of only 5.3 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00138-0

文献信息

• Organophosphorous Compounds for the Activation of Gamma/Delta T Cells
  申请人：Jomaa Hassan

  公开号：US20080249067A1

  公开（公告）日：2008-10-09

  The present invention describes organophosphorus compounds of general formula (I) their preparation and their uses in the activation of gamma/delta T-cells, in the screening of GcpE and LytB enzyme inhibitors and in the prophylaxis and treatment of diseases in humans and animals.
• US7399756B2
  申请人：——

  公开号：US7399756B2

  公开（公告）日：2008-07-15
• US7871992B2
  申请人：——

  公开号：US7871992B2

  公开（公告）日：2011-01-18
• Replacing the pyrophosphate group of HMB-PP by a diphosphonate function abrogates Its potential to activate human γδ T cells but does not lead to competitive antagonism
  作者：Armin Reichenberg、Martin Hintz、Yvonne Kletschek、Tanja Kuhl、Christian Haug、Rosel Engel、Jens Moll、Dmitry N Ostrovsky、Hassan Jomaa、Matthias Eberl

  DOI：10.1016/s0960-894x(03)00138-0

  日期：2003.4

  The immunological characterization of (E)-4-hydroxy-3-methyl-but-2-enyl pyrophosphate (HMB-PP), and its methylenediphosphonate analogue, HMB-PCP, is described. With an EC50 of 0.1-0.2 nM, HMB-PP is significantly more potent in stimulating human Vgamma9/Vdelta2 T cells than any other compound described so far. However, replacing the pyrophosphate by a P-CH2-P function abrogates the bioactivity drastically, with HMB-PCP having a EC50 of only 5.3 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.