ethyl 2-[[(2,6-diisopropylphenoxy)(methoxymethyl)phosphoryl]amino]acetate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-[[(2,6-diisopropylphenoxy)(methoxymethyl)phosphoryl]amino]acetate
• 英文别名: Ethyl 2-[[[2,6-di(propan-2-yl)phenoxy]-(methoxymethyl)phosphoryl]amino]acetate；ethyl 2-[[[2,6-di(propan-2-yl)phenoxy]-(methoxymethyl)phosphoryl]amino]acetate
• 化学式: C₁₈H₃₀NO₅P
• 分子量: 371.414
• InChiKey: PRZANMBXKHVQRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-[[(2,6-diisopropylphenoxy)(methoxymethyl)phosphoryl]amino]acetate 在 ChiralPak AD-H 作用下， 以 正己烷 、 异丙醇 为溶剂， 生成 ethyl 2-[[(2,6-diisopropylphenoxy)(methoxymethyl)phosphoryl]amino]acetate 、 ethyl 2-[[(2,6-diisopropylphenoxy)(methoxymethyl)phosphoryl]amino]acetate
  参考文献：
  名称：

  Oral Delivery of Propofol with Methoxymethylphosphonic Acid as the Delivery Vehicle

  摘要：

  Phosphonamidate 3a of methoxymethylphosphonic acid (MMPA) with propofol (l) and L-alanine ethyl ester was found to be an efficient scaffold for the oral delivery of compound 1. The synthesis and evaluation of MMPA based phosphonamidates of compound 1, HSK3486 (2), and other phenolic drugs revealed the general application of MMPA as the effective delivery vehicle for phenolic drugs. On the basis of plasma concentrations of compound 1 and SN38 (14), the oral bioavailability of compound 3a and 15 in beagle dogs was found to be 97.6% and 34.1%, respectively.

  DOI：

  10.1021/acs.jmedchem.7b01133
• 作为产物：
  描述：

  (methoxymethyl)phosphonic dichloride 、 丙泊酚 、 2-胺基乙酸乙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以5 g的产率得到ethyl 2-[[(2,6-diisopropylphenoxy)(methoxymethyl)phosphoryl]amino]acetate
  参考文献：
  名称：

  Oral Delivery of Propofol with Methoxymethylphosphonic Acid as the Delivery Vehicle

  摘要：

  Phosphonamidate 3a of methoxymethylphosphonic acid (MMPA) with propofol (l) and L-alanine ethyl ester was found to be an efficient scaffold for the oral delivery of compound 1. The synthesis and evaluation of MMPA based phosphonamidates of compound 1, HSK3486 (2), and other phenolic drugs revealed the general application of MMPA as the effective delivery vehicle for phenolic drugs. On the basis of plasma concentrations of compound 1 and SN38 (14), the oral bioavailability of compound 3a and 15 in beagle dogs was found to be 97.6% and 34.1%, respectively.

  DOI：

  10.1021/acs.jmedchem.7b01133

文献信息

• [EN] PHOSPHAMIDE DERIVATIVE, METHOD FOR MANUFACTURING THE SAME, AND USES THEREOF<br/>[FR] DÉRIVÉ DE PHOSPHAMIDE, SON PROCÉDÉ DE FABRICATION ET SES UTILISATIONS<br/>[ZH] 一种磷酰胺衍生物及制备方法和用途
  申请人：SICHUAN HAISCO PHARMACEUTICAL CO LTD

  公开号：WO2017133517A1

  公开（公告）日：2017-08-10

  公开了一种磷酰胺衍生物及制备方法和用途。特别公开了一种通式(I)所示化合物及其药学上可接受的盐或立体异构体 (I)，其中，G、L、Q、s如说明书中所定义。
• Oral Delivery of Propofol with Methoxymethylphosphonic Acid as the Delivery Vehicle
  作者：Yonggang Wei、Guanpeng Qiu、Bailin Lei、Linlin Qin、Hongzhu Chu、Yonghua Lu、Guozhi Zhu、Qiu Gao、Qingping Huang、Guofei Qian、Pengfei Liao、Xinfeng Luo、Xiaowei Zhang、Chen Zhang、Yao Li、Suxin Zheng、Yan Yu、Pingming Tang、Jia Ni、Pangke Yan、Yi Zhou、Pan Li、Xia Huang、Aisheng Gong、Jianyu Liu

  DOI：10.1021/acs.jmedchem.7b01133

  日期：2017.10.26

  Phosphonamidate 3a of methoxymethylphosphonic acid (MMPA) with propofol (l) and L-alanine ethyl ester was found to be an efficient scaffold for the oral delivery of compound 1. The synthesis and evaluation of MMPA based phosphonamidates of compound 1, HSK3486 (2), and other phenolic drugs revealed the general application of MMPA as the effective delivery vehicle for phenolic drugs. On the basis of plasma concentrations of compound 1 and SN38 (14), the oral bioavailability of compound 3a and 15 in beagle dogs was found to be 97.6% and 34.1%, respectively.