diethyl 2-acetamido-2-(4-(2-((4-chlorobenzoyl)oxy)acetyl)phenethyl)malonate

• 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: diethyl 2-acetamido-2-(4-(2-((4-chlorobenzoyl)oxy)acetyl)phenethyl)malonate
• 英文别名: diethyl 2-acetylamino-2-[4-(2-(4-chlorobenzoyloxy)acetyl)phenethyl]malonate；Diethyl 2-acetamido-2-[2-[4-[2-(4-chlorobenzoyl)oxyacetyl]phenyl]ethyl]propanedioate；diethyl 2-acetamido-2-[2-[4-[2-(4-chlorobenzoyl)oxyacetyl]phenyl]ethyl]propanedioate
• 化学式: C₂₆H₂₈ClNO₈
• 分子量: 517.963
• InChiKey: SWRCYQTWVZIJAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diethyl 2-acetamido-2-(4-(2-((4-chlorobenzoyl)oxy)acetyl)phenethyl)malonate 在 乙酰胺 、 三氟化硼乙醚 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 40.0h， 以47.2%的产率得到diethyl 2-acetamido-2-(4-(2-(4-chlorophenyl)oxazol-4-yl)phenethyl)malonate
  参考文献：
  名称：

  Discovery of oxazole and triazole derivatives as potent and selective S1P1 agonists through pharmacophore-guided design

  摘要：

  We have discovered a series of triazole/oxazole-containing 2-substituted 2-aminopropane-1,3-diol derivatives as potent and selective S1P(1) agonists (prodrugs) based on pharmacophore-guided rational design. Most compounds showed high affinity and selectivity for S1P(1) receptor. Compounds 19b, 19d and 19p displayed clear dose responsiveness in the lymphocyte reduction model when administered orally at doses of 0.3, 1.0, 3.0 mg/kg with reduced effect on heart rate. These three compounds were also identified to have favorable pharmacokinetic properties. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.081
• 作为产物：
  描述：

  2-乙酰氨基-2-苯乙基丙二醇二乙酯 在 aluminum (III) chloride 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 7.5h， 生成 diethyl 2-acetamido-2-(4-(2-((4-chlorobenzoyl)oxy)acetyl)phenethyl)malonate
  参考文献：
  名称：

  Discovery of oxazole and triazole derivatives as potent and selective S1P1 agonists through pharmacophore-guided design

  摘要：

  We have discovered a series of triazole/oxazole-containing 2-substituted 2-aminopropane-1,3-diol derivatives as potent and selective S1P(1) agonists (prodrugs) based on pharmacophore-guided rational design. Most compounds showed high affinity and selectivity for S1P(1) receptor. Compounds 19b, 19d and 19p displayed clear dose responsiveness in the lymphocyte reduction model when administered orally at doses of 0.3, 1.0, 3.0 mg/kg with reduced effect on heart rate. These three compounds were also identified to have favorable pharmacokinetic properties. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.081

文献信息

• Discovery of oxazole and triazole derivatives as potent and selective S1P1 agonists through pharmacophore-guided design
  作者：Yulin Tian、Jing Jin、Xiaojian Wang、Jinping Hu、Qiong Xiao、Wanqi Zhou、Xiaoguang Chen、Dali Yin

  DOI：10.1016/j.ejmech.2014.07.081

  日期：2014.10

  We have discovered a series of triazole/oxazole-containing 2-substituted 2-aminopropane-1,3-diol derivatives as potent and selective S1P(1) agonists (prodrugs) based on pharmacophore-guided rational design. Most compounds showed high affinity and selectivity for S1P(1) receptor. Compounds 19b, 19d and 19p displayed clear dose responsiveness in the lymphocyte reduction model when administered orally at doses of 0.3, 1.0, 3.0 mg/kg with reduced effect on heart rate. These three compounds were also identified to have favorable pharmacokinetic properties. (C) 2014 Elsevier Masson SAS. All rights reserved.