3β-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)ursolic acid 28-methyl ester | 1173241-20-7

• 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-(2,3,4,6-tetra-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)-1,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxy-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
• CAS: 1173241-20-7
• 化学式: C₆₅H₇₆O₁₂
• 分子量: 1049.31
• InChiKey: BDDNXDHUZJDXIE-NWVYERFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.5
• 重原子数：
  77
• 可旋转键数：
  17
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3β-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)ursolic acid 28-methyl ester 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以90%的产率得到3β-O-(βD-glucopyranosyl)-ursolic acid 28-methyl ester
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Analogs of Methyl Ursolate 3-O-β-Chacotrioside as H5N1 Viral Entry Inhibitors

  摘要：

  The earliest stage of influenza virus infection is the viral entry to the host cell. In our previous work, we discovered the first three small molecule H5N1 viral entry inhibitors 1-3. Here, based on saponin 3, methyl ursolate 3-O-beta-chacotrioside, several analogs were synthesized and evaluated to understand the structure-activity relationships of this type of compound on the H5N1 viral entry inhibitory activity. The preliminary studies demonstrated that unlike saponins 1 and 2, it is possible to reduce the 3-O-chacotriosyl residue of compound 3 to a disaccharide without affecting the viral entry activities significantly. The results obtained will render new clues to the understanding of the antiviral profile for these types of compounds.

  DOI：

  10.1080/07328303.2012.687060
• 作为产物：
  描述：

  乌宋酸甲酯 、 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到3β-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)ursolic acid 28-methyl ester
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Analogs of Methyl Ursolate 3-O-β-Chacotrioside as H5N1 Viral Entry Inhibitors

  摘要：

  The earliest stage of influenza virus infection is the viral entry to the host cell. In our previous work, we discovered the first three small molecule H5N1 viral entry inhibitors 1-3. Here, based on saponin 3, methyl ursolate 3-O-beta-chacotrioside, several analogs were synthesized and evaluated to understand the structure-activity relationships of this type of compound on the H5N1 viral entry inhibitory activity. The preliminary studies demonstrated that unlike saponins 1 and 2, it is possible to reduce the 3-O-chacotriosyl residue of compound 3 to a disaccharide without affecting the viral entry activities significantly. The results obtained will render new clues to the understanding of the antiviral profile for these types of compounds.

  DOI：

  10.1080/07328303.2012.687060

文献信息

• Discovery of the First Series of Small Molecule H5N1 Entry Inhibitors
  作者：Gaopeng Song、Sen Yang、Wei Zhang、Yingli Cao、Peng Wang、Ning Ding、Zaihong Zhang、Ying Guo、Yingxia Li

  DOI：10.1021/jm900275m

  日期：2009.12.10

  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.