2-(benzylamino)-2-(dimethoxyphosphoryl)propyl acetate

• 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-(benzylamino)-2-(dimethoxyphosphoryl)propyl acetate
• 英文别名: [2-(Benzylamino)-2-dimethoxyphosphorylpropyl] acetate；[2-(benzylamino)-2-dimethoxyphosphorylpropyl] acetate
• 化学式: C₁₄H₂₂NO₅P
• 分子量: 315.306
• InChiKey: YAWXHPDMKTVDIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  过氧化乙酰丙酮 、 亚磷酸二甲酯 、 苄胺 在 苯膦酸 作用下， 以 neat (no solvent) 为溶剂， 反应 4.5h， 以56%的产率得到2-(benzylamino)-2-(dimethoxyphosphoryl)propyl acetate
  参考文献：
  名称：

  000Synthesis of new α-aminophosphonates: Evaluation as anti-inflammatory agents and QSAR studies

  摘要：

  In this paper, we report the synthesis of a new series of alpha-aminophosphonates derivatives based in an efficient three-component reaction. All compounds prepared showed significant anti-inflammatory activity, being the compounds 1a, 1c, 1d, 1f, 2b and 2c the most promising ones, in terms of maximal efficacy (over 95%), potency (ED50 range between 0.7 and 10.1 mg/ear) and relative potency (range from 0.04 to 0.67). Compounds 1a, 1c, 1d and 1f significantly decrease the number of neutrophils (range from 46.7 to 63.0%) and monocytes (18.9-34.1%) in blood samples from the orbital sinus. Additionally, QSAR model revealed that the spherical molecular shape and the location of the HOMO on the phenyl ring improves the anti-inflammatory activity of the compounds. The values of R-2, Q(2), s and F statistical parameters and the QUIK, asymptotic Q(2) and Overfitting rules validate the descriptive and predictive ability of the QSAR model. Altogether these results suggest that these new a-aminophosphonates are potential agents for the treatment of inflammation.

  DOI：

  10.1016/j.bmc.2018.12.041

文献信息

• 000Synthesis of new α-aminophosphonates: Evaluation as anti-inflammatory agents and QSAR studies
  作者：Ivan Romero-Estudillo、José Luis Viveros-Ceballos、Obed Cazares-Carreño、Angelina González-Morales、Berenice Flores de Jesús、Misael López-Castillo、Rodrigo Said Razo-Hernández、Gabriela Castañeda-Corral、Mario Ordóñez

  DOI：10.1016/j.bmc.2018.12.041

  日期：2019.6

  In this paper, we report the synthesis of a new series of alpha-aminophosphonates derivatives based in an efficient three-component reaction. All compounds prepared showed significant anti-inflammatory activity, being the compounds 1a, 1c, 1d, 1f, 2b and 2c the most promising ones, in terms of maximal efficacy (over 95%), potency (ED50 range between 0.7 and 10.1 mg/ear) and relative potency (range from 0.04 to 0.67). Compounds 1a, 1c, 1d and 1f significantly decrease the number of neutrophils (range from 46.7 to 63.0%) and monocytes (18.9-34.1%) in blood samples from the orbital sinus. Additionally, QSAR model revealed that the spherical molecular shape and the location of the HOMO on the phenyl ring improves the anti-inflammatory activity of the compounds. The values of R-2, Q(2), s and F statistical parameters and the QUIK, asymptotic Q(2) and Overfitting rules validate the descriptive and predictive ability of the QSAR model. Altogether these results suggest that these new a-aminophosphonates are potential agents for the treatment of inflammation.