6α-O-benzoyl chlorogenin | 1173241-36-5

• 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: 6α-O-benzoyl chlorogenin
• 英文别名: 6-O-benzoylchlorogenin；[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18S,19S)-16-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-19-yl] benzoate
• CAS: 1173241-36-5
• 化学式: C₃₄H₄₈O₅
• 分子量: 536.752
• InChiKey: HQASIVQYCUZNGZ-WPPXBYGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  39
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6α-O-benzoyl chlorogenin 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 5.0h， 生成 6-O-benzoylchlorogenin 3-O-(6-O-methyl-β-D-glucopyranoside)
  参考文献：
  名称：

  Structure–activity relationships of saponin derivatives: A series of entry inhibitors for highly pathogenic H5N1 influenza virus

  摘要：

  The occurrence of highly pathogenic avian influenza virus H5N1 highlights the urgent need for new classes of antiviral drugs. Theoretically, each of steps in influenza viral life cycle can be a target of antiviral therapeutics. However, up to date, no licenced entry inhibitor drug is available for H5N1 or any other influenza viruses. Our strategy for developing new anti-influenza therapeutics is to target the interaction between HA and sialic acid which is influenza viral receptor presented on host cell surface. Here, based on our previously discovered small molecule inhibitor saponin 1, intensive SAR studies around the sugar chain and aglycone were conducted. The results showed that both the chacotriosyl residue and the chlorogenin moiety of active compound 1 are important for the antiviral activity, although several subtle modifications can be made on particular positions. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.022
• 作为产物：
  描述：

  3β-O-benzyl-6α-O-benzoyl chlorogenin 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 以98.4%的产率得到6α-O-benzoyl chlorogenin
  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