1-[(1-methylethoxy)carbonyloxy]methyl 2-[(2,6-dichlorophenyl)amino]phenylacetate | 1264635-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[(1-methylethoxy)carbonyloxy]methyl 2-[(2,6-dichlorophenyl)amino]phenylacetate
• 英文别名: Propan-2-yloxycarbonyloxymethyl 2-[2-(2,6-dichloroanilino)phenyl]acetate
• CAS: 1264635-62-2
• 化学式: C₁₉H₁₉Cl₂NO₅
• 分子量: 412.27
• InChiKey: CWFSRKOXOMBPCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  氯甲基碳酸异丙酯 在 sodium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基乙酰胺 、 乙腈 为溶剂， 反应 22.92h， 生成 1-[(1-methylethoxy)carbonyloxy]methyl 2-[(2,6-dichlorophenyl)amino]phenylacetate
  参考文献：
  名称：

  Synthesis, Characterization, and Biological Evaluation of Novel Diclofenac Prodrugs

  摘要：

  Diclofenac ester prodrugs (4, 5, 6) were synthesized and evaluated in vitro and in vivo for their potential use for oral delivery, with the aim of obtaining enzymatically labile and less ulceration drugs than the parent drug diclofenac sodium (1a). Prodrugs 4, 5; 6 were found to be potent anti-inflammatory drugs with less ulcerogenic potential than the parent diclofenac sodium. Prodrugs 4, 5, 6 rapidly underwent enzymatic hydrolysis to release the parent drug diclofenac in 30-60 min in rat liver microsomes (RLM) and rat plasma (RP). Prodrugs were found to be more lipophilic when the partition coefficient was measured in 1-octanol and buffer system at pH 7.4 and 3.0. Diclofenac prodrugs 4, 5, 6 were found to be crystalline in nature (analyzed by PXRD). Prodrug 4 was found to be a superior candidate for the treatment of chronic inflammatory diseases.

  DOI：

  10.1021/jm101095e

文献信息

• Synthesis, Characterization, and Biological Evaluation of Novel Diclofenac Prodrugs
  作者：Babasaheb P. Bandgar、Rajendra Janardan Sarangdhar、Fakrudeen Ali Ahamed、Santosh Viswakarma

  DOI：10.1021/jm101095e

  日期：2011.3.10

  Diclofenac ester prodrugs (4, 5, 6) were synthesized and evaluated in vitro and in vivo for their potential use for oral delivery, with the aim of obtaining enzymatically labile and less ulceration drugs than the parent drug diclofenac sodium (1a). Prodrugs 4, 5; 6 were found to be potent anti-inflammatory drugs with less ulcerogenic potential than the parent diclofenac sodium. Prodrugs 4, 5, 6 rapidly underwent enzymatic hydrolysis to release the parent drug diclofenac in 30-60 min in rat liver microsomes (RLM) and rat plasma (RP). Prodrugs were found to be more lipophilic when the partition coefficient was measured in 1-octanol and buffer system at pH 7.4 and 3.0. Diclofenac prodrugs 4, 5, 6 were found to be crystalline in nature (analyzed by PXRD). Prodrug 4 was found to be a superior candidate for the treatment of chronic inflammatory diseases.