2-(2-(4-isobutylphenyl)propanoyloxy)ethyl 4,5-diacetoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate | 1174523-54-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(2-(4-isobutylphenyl)propanoyloxy)ethyl 4,5-diacetoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate
• 英文别名: 2 [2-[4-(2-methylpropyl)phenyl]propanoyloxy]ethyl-4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylate；2-[2-[4-(2-Methylpropyl)phenyl]propanoyloxy]ethyl 4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylate
• CAS: 1174523-54-6
• 化学式: C₃₄H₃₂O₁₀
• 分子量: 600.622
• InChiKey: IJBBMBQGXYOQHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(2-(4-isobutylphenyl)propanoyloxy)ethyl 4,5-diacetoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate 在 水 、 三乙胺 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以76%的产率得到2-(2-(4-isobutylphenyl)propanoyloxy)ethyl 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate
  参考文献：
  名称：

  Bone-targeting glycol and NSAIDS ester prodrugs of rhein: Synthesis, hydroxyapatite affinity, stability, anti-inflammatory, ulcerogenicity index and pharmacokinetics studies

  摘要：

  Although rhein and NSAIDs are potent anti-inflammatory drugs, their use has been limited by the high incidence of gastrointestinal erosions and the necessity to deliver the drug to specific sites of target organ. Using the prodrug approach, a series of rhein-NSAIDs prodrugs containing anthraquinone bone-targeting moiety were synthesized by linking rhein with NSAIDs through glycol ester. The target compounds demonstrated significant capability of binding to HAP and were hydrolytically activated in physiological conditions. Hybrid rhein-NSAIDs prodrugs exhibited significant anti-inflammatory activity, moreover, the tested compounds were also found to possess less degree of ulcerogenic potential. Our pharmacokinetic studies of 7e demonstrated this prodrug is a potential candidate for a slower and sustained release form of rhein. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.053
• 作为产物：
  描述：

  大黄酸 在 草酰氯 、 硫酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-(2-(4-isobutylphenyl)propanoyloxy)ethyl 4,5-diacetoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate
  参考文献：
  名称：

  Bone-targeting glycol and NSAIDS ester prodrugs of rhein: Synthesis, hydroxyapatite affinity, stability, anti-inflammatory, ulcerogenicity index and pharmacokinetics studies

  摘要：

  Although rhein and NSAIDs are potent anti-inflammatory drugs, their use has been limited by the high incidence of gastrointestinal erosions and the necessity to deliver the drug to specific sites of target organ. Using the prodrug approach, a series of rhein-NSAIDs prodrugs containing anthraquinone bone-targeting moiety were synthesized by linking rhein with NSAIDs through glycol ester. The target compounds demonstrated significant capability of binding to HAP and were hydrolytically activated in physiological conditions. Hybrid rhein-NSAIDs prodrugs exhibited significant anti-inflammatory activity, moreover, the tested compounds were also found to possess less degree of ulcerogenic potential. Our pharmacokinetic studies of 7e demonstrated this prodrug is a potential candidate for a slower and sustained release form of rhein. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.053

文献信息

• Bone-targeting glycol and NSAIDS ester prodrugs of rhein: Synthesis, hydroxyapatite affinity, stability, anti-inflammatory, ulcerogenicity index and pharmacokinetics studies
  作者：Jin Cai、Yanbing Duan、Jia Yu、Junqing Chen、Meng Chao、Min Ji

  DOI：10.1016/j.ejmech.2012.07.053

  日期：2012.9

  Although rhein and NSAIDs are potent anti-inflammatory drugs, their use has been limited by the high incidence of gastrointestinal erosions and the necessity to deliver the drug to specific sites of target organ. Using the prodrug approach, a series of rhein-NSAIDs prodrugs containing anthraquinone bone-targeting moiety were synthesized by linking rhein with NSAIDs through glycol ester. The target compounds demonstrated significant capability of binding to HAP and were hydrolytically activated in physiological conditions. Hybrid rhein-NSAIDs prodrugs exhibited significant anti-inflammatory activity, moreover, the tested compounds were also found to possess less degree of ulcerogenic potential. Our pharmacokinetic studies of 7e demonstrated this prodrug is a potential candidate for a slower and sustained release form of rhein. (C) 2012 Elsevier Masson SAS. All rights reserved.