3β-O-[2,4-di-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl]-12-en-28-oic acid ethyl ester

• 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-[2,4-di-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl]-12-en-28-oic acid ethyl ester
• 英文别名: ethyl (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5S,6R)-4-hydroxy-6-(hydroxymethyl)-3,5-bis[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-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
• 化学式: C₅₀H₈₂O₁₆
• 分子量: 939.191
• InChiKey: CLXRDCMVSSYLSH-HCLBJXDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  66
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  244
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  溴乙烷 、 3β-O-[2,4-di-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl]-12-en-28-oic acid allyl ester 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以96%的产率得到3β-O-[2,4-di-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl]-12-en-28-oic acid ethyl ester
  参考文献：
  名称：

  Structure–activity relationships of 3-O-β-chacotriosyl ursolic acid derivatives as novel H5N1 entry inhibitors

  摘要：

  A series of methyl ursolate 3-O-beta-chacotrioside analogs have been designed, synthesized and evaluated as H5N1 entry inhibitors based on a small molecule inhibitor saponin 3 previously discovered by us. Detailed structure-activity relationships (SARs) studies on the aglycone of compound 3 indicated that both the type of pentacyclic triterpene and the subtle modification of ursolic acid as an aglycon had key influences on the antiviral activity. These results suggested that either the introduction of a disubstituted amide structure at the 17-COOH of ursolic acid or alteration of the C-3 configuration of ursolic acid from 3 beta-to 3 alpha-forms was helpful to significantly improve the selective index while keeping their antiviral activities. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.029

文献信息

• Structure–activity relationships of 3-O-β-chacotriosyl ursolic acid derivatives as novel H5N1 entry inhibitors
  作者：Gaopeng Song、Xintian Shen、Sumei Li、Yibin Li、Yunpeng Liu、Yushan Zheng、Ruheng Lin、Jihong Fan、Hanming Ye、Shuwen Liu

  DOI：10.1016/j.ejmech.2015.02.029

  日期：2015.3

  A series of methyl ursolate 3-O-beta-chacotrioside analogs have been designed, synthesized and evaluated as H5N1 entry inhibitors based on a small molecule inhibitor saponin 3 previously discovered by us. Detailed structure-activity relationships (SARs) studies on the aglycone of compound 3 indicated that both the type of pentacyclic triterpene and the subtle modification of ursolic acid as an aglycon had key influences on the antiviral activity. These results suggested that either the introduction of a disubstituted amide structure at the 17-COOH of ursolic acid or alteration of the C-3 configuration of ursolic acid from 3 beta-to 3 alpha-forms was helpful to significantly improve the selective index while keeping their antiviral activities. (C) 2015 Elsevier Masson SAS. All rights reserved.