1-{3-[1-(p-chlorobenzoyl)-5-methoxy-2-methylindol-acetoxy]}-8-trityloxy-3,6-dioxaoctane | 883992-08-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-{3-[1-(p-chlorobenzoyl)-5-methoxy-2-methylindol-acetoxy]}-8-trityloxy-3,6-dioxaoctane
• CAS: 883992-08-3
• 化学式: C₄₄H₄₂ClNO₇
• 分子量: 732.273
• InChiKey: SZMOZEPPGPDARQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.43
• 重原子数：
  53.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  85.22
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-{3-[1-(p-chlorobenzoyl)-5-methoxy-2-methylindol-acetoxy]}-8-trityloxy-3,6-dioxaoctane 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以64%的产率得到2-[2-(2-羟基乙氧基)乙氧基]乙基2-[1-(4-氯苯甲酰基)-5-甲氧基-2-甲基吲哚-3-基]乙酸酯
  参考文献：
  名称：

  Synthesis and stability of two indomethacin prodrugs

  摘要：

  The purpose of this study was to synthesize and study the in vitro enzymatic and non-enzymatic hydrolysis of indomethacin-TEG ester and amide prodrugs. It was found that the ester conjugate 10 was comparatively stable between pH 3 and 6 (half-life >90 h), with a half-life equal to 5.2 h in 80% buffered plasma. In contrast, the amide conjugate 12 appeared to be stable over the entire pH range studied with the only observed degradation being cleavage of the indolic N-4-chlorobenzoyl moiety. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.003
• 作为产物：
  描述：

  吲哚美辛 以 四氢呋喃 为溶剂， 反应 27.0h， 生成 1-{3-[1-(p-chlorobenzoyl)-5-methoxy-2-methylindol-acetoxy]}-8-trityloxy-3,6-dioxaoctane
  参考文献：
  名称：

  Synthesis and stability of two indomethacin prodrugs

  摘要：

  The purpose of this study was to synthesize and study the in vitro enzymatic and non-enzymatic hydrolysis of indomethacin-TEG ester and amide prodrugs. It was found that the ester conjugate 10 was comparatively stable between pH 3 and 6 (half-life >90 h), with a half-life equal to 5.2 h in 80% buffered plasma. In contrast, the amide conjugate 12 appeared to be stable over the entire pH range studied with the only observed degradation being cleavage of the indolic N-4-chlorobenzoyl moiety. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.003