rhein diethylene glycol ester | 1174523-50-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: rhein diethylene glycol ester
• 英文别名: 2-(2-Hydroxyethoxy)ethyl 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylate
• CAS: 1174523-50-2
• 化学式: C₁₉H₁₆O₈
• 分子量: 372.331
• InChiKey: HIGKJUXIOUJULQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  大黄酸 、 二乙二醇 在 硫酸 作用下， 反应 1.0h， 以88%的产率得到rhein diethylene glycol ester
  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