propyl 6-O-(2'-(4'-isobutylphenyl)propionyl)-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: propyl 6-O-(2'-(4'-isobutylphenyl)propionyl)-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R)-3,4,5-trihydroxy-6-propoxyoxan-2-yl]methyl 2-[4-(2-methylpropyl)phenyl]propanoate
• 化学式: C₂₂H₃₄O₇
• 分子量: 410.508
• InChiKey: FOXOIFKRTQLRCA-IDMAATAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  propyl 6-O-(2'-(4'-isobutylphenyl)propionyl)-D-glucopyranoside 在 phosphate buffer 、 potassium chloride 作用下， 生成 布洛芬 、 n-propyl D-glucopyranoside
  参考文献：
  名称：

  Pharmacological activity and hydrolysis behavior of novel ibuprofen glucopyranoside conjugates

  摘要：

  Novel ester prodrugs (II, III and IV) of ibuprofen (I) were synthesized using a-methyl, ethyl and propyl glucopyranoside as promoieties and tested for their anti-inflammatory, analgesic and ulcerogenic activities. Study of their chemical hydrolysis in aqueous buffer (PH 3.0-10.0) showed that these compounds acted as true prodrugs of ibuprofen, giving the ibuprofen and alkyl glucopyranoside. Additionally, all the derivatives studied did cleave rapidly inside the biological system and on oral administration did elicit a pharmacological profile quite similar to that of ibuprofen, but, unlike this drug, they displayed reduced gastric ulceration. In conclusion, these alkyl glucopyranoside esters have promising properties as prodrugs for oral delivery of ibuprofen. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.05.014
• 作为产物：
  描述：

  布洛芬 、 n-propyl D-glucopyranoside 在 Novozym 435 lipase 作用下， 以 乙腈 为溶剂， 反应 144.0h， 以26.3%的产率得到propyl 6-O-(2'-(4'-isobutylphenyl)propionyl)-D-glucopyranoside
  参考文献：
  名称：

  Pharmacological activity and hydrolysis behavior of novel ibuprofen glucopyranoside conjugates

  摘要：

  Novel ester prodrugs (II, III and IV) of ibuprofen (I) were synthesized using a-methyl, ethyl and propyl glucopyranoside as promoieties and tested for their anti-inflammatory, analgesic and ulcerogenic activities. Study of their chemical hydrolysis in aqueous buffer (PH 3.0-10.0) showed that these compounds acted as true prodrugs of ibuprofen, giving the ibuprofen and alkyl glucopyranoside. Additionally, all the derivatives studied did cleave rapidly inside the biological system and on oral administration did elicit a pharmacological profile quite similar to that of ibuprofen, but, unlike this drug, they displayed reduced gastric ulceration. In conclusion, these alkyl glucopyranoside esters have promising properties as prodrugs for oral delivery of ibuprofen. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.05.014

文献信息

• Pharmacological activity and hydrolysis behavior of novel ibuprofen glucopyranoside conjugates
  作者：Xiangguo Zhao、Xinyi Tao、Dongzhi Wei、Qingxun Song

  DOI：10.1016/j.ejmech.2006.05.014

  日期：2006.11

  Novel ester prodrugs (II, III and IV) of ibuprofen (I) were synthesized using a-methyl, ethyl and propyl glucopyranoside as promoieties and tested for their anti-inflammatory, analgesic and ulcerogenic activities. Study of their chemical hydrolysis in aqueous buffer (PH 3.0-10.0) showed that these compounds acted as true prodrugs of ibuprofen, giving the ibuprofen and alkyl glucopyranoside. Additionally, all the derivatives studied did cleave rapidly inside the biological system and on oral administration did elicit a pharmacological profile quite similar to that of ibuprofen, but, unlike this drug, they displayed reduced gastric ulceration. In conclusion, these alkyl glucopyranoside esters have promising properties as prodrugs for oral delivery of ibuprofen. (c) 2006 Elsevier Masson SAS. All rights reserved.