11β,17α-dihydroxy-3,20-dioxopregna-1,4-dien-21-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 88179-95-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 11β,17α-dihydroxy-3,20-dioxopregna-1,4-dien-21-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• CAS: 88179-95-7
• 化学式: C₃₅H₄₆O₁₄
• 分子量: 690.742
• InChiKey: UHNZIVCONFLXQV-BRMAWRRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  49.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  198.26
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  11β,17α-dihydroxy-3,20-dioxopregna-1,4-dien-21-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 以125 mg的产率得到11β,17α-dihydroxy-3,20-dioxopregna-1,4-dien-21-yl β-D-glucopyranoside
  参考文献：
  名称：

  WO2023/80784

  摘要：

  公开号：
• 作为产物：
  描述：

  泼尼松龙 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 生成 11β,17α-dihydroxy-3,20-dioxopregna-1,4-dien-21-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  WO2023/80784

  摘要：

  公开号：

文献信息

• A colon-specific drug-delivery system based on drug glycosides and the glycosidases of colonic bacteria
  作者：David R. Friend、George W. Chang

  DOI：10.1021/jm00369a005

  日期：1984.3

  Steroid glycosides and the unique glycosidase activity of the colonic microflora form the basis of a new colon-specific drug-delivery system. Drug glycosides are hydrophilic and, thus, poorly absorbed from the small intestine. Once such a glycoside reaches the colon it can be cleaved by bacterial glycosidases, releasing the free drug to be absorbed by the colonic mucosa. This concept was illustrated with dexamethasone 21-beta-D-glucoside (1) and prednisolone 21-beta-D-glucoside (2), two prodrugs that may be useful in treating inflammatory bowel disease. Hydrolysis of the prodrugs by beta-glucosidase and fecal homogenates in vitro released the free steroids. Glucosides 1 and 2 were administered to rats intragastrically to determine when and where the free steroids were released. Unmodified dexamethasone (3) and prednisolone (4) were also given to rats intragastrically to compare absorption of the glucosides with the free steroids. Both glucosides were found to reach the rat lower intestine in 4-5 h, where they were rapidly hydrolyzed, releasing the free steroids. Delivery of steroid 3 (via glucoside 1) was more specific than that of steroid 4 (via glucoside 2): nearly 60% of an oral dose of glucoside 1 reached the cecum, whereas less than 15% of glucoside 2 reached the cecum. When free steroids 3 and 4 were administered orally, they were almost exclusively absorbed in the small intestine: less than 1% of an oral dose of each reached the cecum.