(((3-(N-(benzyloxy)acetamido)propyl)phosphoryl)bis(oxy))bis(ethane-1,1-diyl) di-tert-butyl bis(carbonate) | 1350649-63-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: (((3-(N-(benzyloxy)acetamido)propyl)phosphoryl)bis(oxy))bis(ethane-1,1-diyl) di-tert-butyl bis(carbonate)
• CAS: 1350649-63-6
• 化学式: C₂₆H₄₂NO₁₁P
• 分子量: 575.593
• InChiKey: INDOTMQLTKGOPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.18
• 重原子数：
  39.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  136.13
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (((3-(N-(benzyloxy)acetamido)propyl)phosphoryl)bis(oxy))bis(ethane-1,1-diyl) di-tert-butyl bis(carbonate) 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 以43%的产率得到1-[3-[Acetyl(hydroxy)amino]propyl-(1-tert-butoxycarbonyloxyethoxy)phosphoryl]oxyethyl tert-butyl carbonate
  参考文献：
  名称：

  Antibacterial and antitubercular activity of fosmidomycin, FR900098, and their lipophilic analogs

  摘要：

  The nonmevalonate pathway (NMP) of isoprene biosynthesis is an exciting new route toward novel antibiotic development. Inhibitors against several enzymes in this pathway are currently under examination. A significant liability of many of these agents is poor cell penetration. To overcome and improve our understanding of this problem, we have synthesized a series of lipophilic, prodrug analogs of fosmidomycin and FR900098, inhibitors of the NMP enzyme Dxr. Several of these compounds show improved antibacterial activity against a panel of organisms relative to the parent compound, including activity against Mycobacterium tuberculosis (Mtb). Our results show that this strategy can be an effective way for improving whole cell activity of NMP inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.123
• 作为产物：
  描述：

  O-苄基羟胺 在 盐酸 、 三甲基溴硅烷 、 四丁基溴化铵 、 sodium hydride 、 potassium carbonate 、 potassium hydrogencarbonate 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 、 二氯甲烷 为溶剂， 反应 42.5h， 生成 (((3-(N-(benzyloxy)acetamido)propyl)phosphoryl)bis(oxy))bis(ethane-1,1-diyl) di-tert-butyl bis(carbonate)
  参考文献：
  名称：

  Antibacterial and antitubercular activity of fosmidomycin, FR900098, and their lipophilic analogs

  摘要：

  The nonmevalonate pathway (NMP) of isoprene biosynthesis is an exciting new route toward novel antibiotic development. Inhibitors against several enzymes in this pathway are currently under examination. A significant liability of many of these agents is poor cell penetration. To overcome and improve our understanding of this problem, we have synthesized a series of lipophilic, prodrug analogs of fosmidomycin and FR900098, inhibitors of the NMP enzyme Dxr. Several of these compounds show improved antibacterial activity against a panel of organisms relative to the parent compound, including activity against Mycobacterium tuberculosis (Mtb). Our results show that this strategy can be an effective way for improving whole cell activity of NMP inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.123