3β-O-[2-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-4,6-O-benzylidene-β-D-glucopyranosyl]-ursolic-28-methyl ester | 1412198-49-2

• 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-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-4,6-O-benzylidene-β-D-glucopyranosyl]-ursolic-28-methyl ester
• CAS: 1412198-49-2
• 化学式: C₇₁H₈₆O₁₅
• 分子量: 1179.45
• InChiKey: ZZKCLNIVXQIIRI-SQDCPCOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.21
• 重原子数：
  86.0
• 可旋转键数：
  12.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  180.81
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  3β-O-[2-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-4,6-O-benzylidene-β-D-glucopyranosyl]-ursolic-28-methyl ester 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 以62%的产率得到3β-O-[2-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl]ursolic-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：

  3β-O-(4,6-O-benzylidene-β-D-glucopyranosyl)ursolic-28-methyl ester 、 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以61 mg的产率得到3β-O-[2-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-4,6-O-benzylidene-β-D-glucopyranosyl]-ursolic-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