[2-[1-[[(2R,3S)-3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl]methyl]triazol-4-yl]-1-phosphonoethyl]phosphonic acid

• 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: [2-[1-[[(2R,3S)-3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl]methyl]triazol-4-yl]-1-phosphonoethyl]phosphonic acid
• 化学式: C₁₄H₂₅N₃O₇P₂
• 分子量: 409.316
• InChiKey: XWIODIOSTMLIGU-OCCSQVGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  158
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [2-[1-[[(2R,3S)-3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl]methyl]triazol-4-yl]-1-phosphonoethyl]phosphonic acid 在 sodium hydroxide 作用下， 反应 0.03h， 生成 sodium (2-(1-((3-methyl-3-(4-methylpent-3-en-1-yl)oxiran-2-yl)methyl)-1H-1,2,3-triazol-4-yl)ethane-1,1-diyl)bis(phosphonate)
  参考文献：
  名称：

  Geranyl and neryl triazole bisphosphonates as inhibitors of geranylgeranyl diphosphate synthase

  摘要：

  When inhibitors of enzymes that utilize isoprenoid pyrophosphates are based on the natural substrates, a significant challenge can be to achieve selective inhibition of a specific enzyme. One element in the design process is the stereochemistry of the isoprenoid olefins. We recently reported preparation of a series of isoprenoid triazoles as potential inhibitors of geranylgeranyl transferase II but these compounds were obtained as a mixture of olefin isomers. We now have accomplished the stereoselective synthesis of these triazoles through the use of epoxy azides for the cycloaddition reaction followed by regeneration of the desired olefin. Both geranyl and neryl derivatives have been prepared as single olefin isomers through parallel reaction sequences. The products were assayed against multiple enzymes as well as in cell culture studies and surprisingly a Z-olefin isomer was found to be a potent and selective inhibitor of geranylgeranyl diphosphate synthase. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.014
• 作为产物：
  描述：

  在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 生成 [2-[1-[[(2R,3S)-3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl]methyl]triazol-4-yl]-1-phosphonoethyl]phosphonic acid
  参考文献：
  名称：

  Geranyl and neryl triazole bisphosphonates as inhibitors of geranylgeranyl diphosphate synthase

  摘要：

  When inhibitors of enzymes that utilize isoprenoid pyrophosphates are based on the natural substrates, a significant challenge can be to achieve selective inhibition of a specific enzyme. One element in the design process is the stereochemistry of the isoprenoid olefins. We recently reported preparation of a series of isoprenoid triazoles as potential inhibitors of geranylgeranyl transferase II but these compounds were obtained as a mixture of olefin isomers. We now have accomplished the stereoselective synthesis of these triazoles through the use of epoxy azides for the cycloaddition reaction followed by regeneration of the desired olefin. Both geranyl and neryl derivatives have been prepared as single olefin isomers through parallel reaction sequences. The products were assayed against multiple enzymes as well as in cell culture studies and surprisingly a Z-olefin isomer was found to be a potent and selective inhibitor of geranylgeranyl diphosphate synthase. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.014