6-phenyl-3-[3-(diethoxyphosphoryl)propyl]oxazolo[4,5-b]pyridin-2(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-phenyl-3-[3-(diethoxyphosphoryl)propyl]oxazolo[4,5-b]pyridin-2(3H)-one
• 英文别名: 3-(3-Diethoxyphosphorylpropyl)-6-phenyl-[1,3]oxazolo[4,5-b]pyridin-2-one
• 化学式: C₁₉H₂₃N₂O₅P
• 分子量: 390.376
• InChiKey: MLFDAQJHXZRSBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-phenyl-3-[3-(diethoxyphosphoryl)propyl]oxazolo[4,5-b]pyridin-2(3H)-one 在 三甲基溴硅烷 、 水 作用下， 以 二氯甲烷 为溶剂， 生成 3-(2-Oxo-6-phenyl-oxazolo[4,5-b]pyridin-3-yl)propylphosphonic acid
  参考文献：
  名称：

  Substitution of the phosphonic acid and hydroxamic acid functionalities of the DXR inhibitor FR900098: An attempt to improve the activity against Mycobacterium tuberculosis

  摘要：

  Two series of FR900098/fosmidomycin analogs were synthesized and evaluated for MtDXR inhibition and Mycobacterium tuberculosis whole-cell activity. The design rationale of these compounds involved the exchange of either the phosphonic acid or the hydroxamic acid part for alternative acidic and metal-coordinating functionalities. The best inhibitors provided IC(50) values in the micromolar range, with a best value of 41 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.005
• 作为产物：
  描述：

  二乙基(3-溴丙基)膦酸酯 在 四(三苯基膦)钯 、 sodium ethanolate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-phenyl-3-[3-(diethoxyphosphoryl)propyl]oxazolo[4,5-b]pyridin-2(3H)-one
  参考文献：
  名称：

  Substitution of the phosphonic acid and hydroxamic acid functionalities of the DXR inhibitor FR900098: An attempt to improve the activity against Mycobacterium tuberculosis

  摘要：

  Two series of FR900098/fosmidomycin analogs were synthesized and evaluated for MtDXR inhibition and Mycobacterium tuberculosis whole-cell activity. The design rationale of these compounds involved the exchange of either the phosphonic acid or the hydroxamic acid part for alternative acidic and metal-coordinating functionalities. The best inhibitors provided IC(50) values in the micromolar range, with a best value of 41 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.005

文献信息

• Fosmidomycin analogues as inhibitors of monoterpenoid indole alkaloid production in Catharanthus roseus cells
  作者：Zoia Mincheva、Martine Courtois、Françoise Andreu、Marc Rideau、Marie-Claude Viaud-Massuard

  DOI：10.1016/j.phytochem.2005.06.002

  日期：2005.8

  Substituted 3-[2-(diethoxyphosphoryl)propyl]oxazolo[4,5-b]pyridine-2(3H)-ones were obtained by functionalization at 6-position with various substituents (aryl, vinyl, carbonyl chains) via reactions catalysed with palladium. We found that these new fosmidomycin analogues inhibited the accumulation of ajmalicine, a marker of monoterpenoid indole alkaloids production in plant cells. Some of them have

  取代的 3-[2-(二乙氧基磷酰基)丙基]恶唑并[4,5-b]吡啶-2(3H)-酮是通过在6-位用各种取代基（芳基、乙烯基、羰基链）通过催化反应获得的钯。我们发现这些新的 fosmidomycin 类似物抑制了 ajmalicine 的积累，ajmalicine 是植物细胞中单萜吲哚生物碱产生的标志物。其中一些具有比磷米霉素更大的抑制作用，并且在100 microM的浓度下完全抑制生物碱的积累。