3β-O-(3,6-di-O-benzoyl-β-D-glucopyranosyl)-ursolic acid 28-methyl ester | 1173241-23-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3β-O-(3,6-di-O-benzoyl-β-D-glucopyranosyl)-ursolic acid 28-methyl ester
• 英文别名: methyl (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5R,6R)-4-benzoyloxy-6-(benzoyloxymethyl)-3,5-dihydroxyoxan-2-yl]oxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
• CAS: 1173241-23-0
• 化学式: C₅₁H₆₈O₁₀
• 分子量: 841.095
• InChiKey: AKKUUGJGHDDSRI-CDADGBGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  61
• 可旋转键数：
  11
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3β-O-(3,6-di-O-benzoyl-β-D-glucopyranosyl)-ursolic acid 28-methyl ester 、 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5R,6R)-4-benzoyloxy-6-(benzoyloxymethyl)-3,5-bis[[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxy]oxan-2-yl]oxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
  参考文献：
  名称：

  Discovery of the First Series of Small Molecule H5N1 Entry Inhibitors

  摘要：

  The occurrence of highly pathogenic avian influenza virus H5N1 highlights the urgent need for new classes of antiviral drugs. Inhibition of H5N1 entry into cells may be an effective strategy. We report the first three small molecule inhibitors saponins with 3-O-beta-chacotriosyl residue, which Showed potent inhibitory activity with IC50 of 7.22-9.25 mu M. The subsequent SAR studies showed the 3-O-beta-chacotriosyl residue was essential for the activity, and the aglycone structure also affected the activity.

  DOI：

  10.1021/jm900275m
• 作为产物：
  描述：

  1-(苯甲酰基氧基)-1H-1,2,3-苯并噻唑 、 3β-O-(βD-glucopyranosyl)-ursolic acid 28-methyl ester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以74.5%的产率得到3β-O-(3,6-di-O-benzoyl-β-D-glucopyranosyl)-ursolic acid 28-methyl ester
  参考文献：
  名称：

  Discovery of the First Series of Small Molecule H5N1 Entry Inhibitors

  摘要：

  The occurrence of highly pathogenic avian influenza virus H5N1 highlights the urgent need for new classes of antiviral drugs. Inhibition of H5N1 entry into cells may be an effective strategy. We report the first three small molecule inhibitors saponins with 3-O-beta-chacotriosyl residue, which Showed potent inhibitory activity with IC50 of 7.22-9.25 mu M. The subsequent SAR studies showed the 3-O-beta-chacotriosyl residue was essential for the activity, and the aglycone structure also affected the activity.

  DOI：

  10.1021/jm900275m