[4-[2-[Benzyl-(3-ethoxy-3-oxopropyl)amino]-1-hydroxyethyl]-2-(2,2-dimethylpropanoyloxy)phenyl] 2,2-dimethylpropanoate | 185448-86-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: [4-[2-[Benzyl-(3-ethoxy-3-oxopropyl)amino]-1-hydroxyethyl]-2-(2,2-dimethylpropanoyloxy)phenyl] 2,2-dimethylpropanoate
• CAS: 185448-86-6
• 化学式: C₃₀H₄₁NO₇
• 分子量: 527.658
• InChiKey: QDEQGUFGAJCTCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [4-[2-[Benzyl-(3-ethoxy-3-oxopropyl)amino]-1-hydroxyethyl]-2-(2,2-dimethylpropanoyloxy)phenyl] 2,2-dimethylpropanoate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 0.67h， 以89%的产率得到[2-(2,2-Dimethylpropanoyloxy)-4-[2-[(3-ethoxy-3-oxopropyl)amino]-1-hydroxyethyl]phenyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Soft β-adrenergic agonists for the topical treatment of psoriasis

  摘要：

  The soft-drug 1 (R = Me, Et) and pro-soft-drug 3 have been prepared as models of topical anti-psoriatic beta-adrenergic agonists. The chemical hydrolysis of 3 proceeded via the acid 18 with a maximum stability at apparent pH similar to 4.0. In the presence of PLCE, the required metabolism of 3 to the soft-drug 1 (R = Et) was achieved, which slowly degraded to the dihydroxy acid 2. Soft-drug 1 (R = Et) was poorly transported across a silicone membrane, whereas the pro-soft-drug 3 was more efficient and the rate increased over the donor apparent pH range 3-8. Soft-drug 1 (R = Et) was a full beta-agonist on the guinea-pig tracheal preparation, whereas the pro-soft-drug 3 produced only slowly developing responses at high concentrations (>10 mu M).

  DOI：

  10.1016/s0223-5234(97)89848-0
• 作为产物：
  描述：

  3,4-二羟基-2'-氯苯乙酮 在 sodium tetrahydroborate 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 [4-[2-[Benzyl-(3-ethoxy-3-oxopropyl)amino]-1-hydroxyethyl]-2-(2,2-dimethylpropanoyloxy)phenyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Soft β-adrenergic agonists for the topical treatment of psoriasis

  摘要：

  The soft-drug 1 (R = Me, Et) and pro-soft-drug 3 have been prepared as models of topical anti-psoriatic beta-adrenergic agonists. The chemical hydrolysis of 3 proceeded via the acid 18 with a maximum stability at apparent pH similar to 4.0. In the presence of PLCE, the required metabolism of 3 to the soft-drug 1 (R = Et) was achieved, which slowly degraded to the dihydroxy acid 2. Soft-drug 1 (R = Et) was poorly transported across a silicone membrane, whereas the pro-soft-drug 3 was more efficient and the rate increased over the donor apparent pH range 3-8. Soft-drug 1 (R = Et) was a full beta-agonist on the guinea-pig tracheal preparation, whereas the pro-soft-drug 3 produced only slowly developing responses at high concentrations (>10 mu M).

  DOI：

  10.1016/s0223-5234(97)89848-0

文献信息

• Soft β-adrenergic agonists for the topical treatment of psoriasis
  作者：HS Gill、S Freeman、WJ Irwin、KA Wilson

  DOI：10.1016/s0223-5234(97)89848-0

  日期：1996.1

  The soft-drug 1 (R = Me, Et) and pro-soft-drug 3 have been prepared as models of topical anti-psoriatic beta-adrenergic agonists. The chemical hydrolysis of 3 proceeded via the acid 18 with a maximum stability at apparent pH similar to 4.0. In the presence of PLCE, the required metabolism of 3 to the soft-drug 1 (R = Et) was achieved, which slowly degraded to the dihydroxy acid 2. Soft-drug 1 (R = Et) was poorly transported across a silicone membrane, whereas the pro-soft-drug 3 was more efficient and the rate increased over the donor apparent pH range 3-8. Soft-drug 1 (R = Et) was a full beta-agonist on the guinea-pig tracheal preparation, whereas the pro-soft-drug 3 produced only slowly developing responses at high concentrations (>10 mu M).