3α-hydroxyurs-12-en-28-oic acid methyl ester | 915-32-2

• 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: 3α-hydroxyurs-12-en-28-oic acid methyl ester
• 英文别名: 3β-O-3α-methyl ursolate；3α-ursolic acid methyl ester；methyl (1S,2R,4aS,6aR,6aS,6bR,8aR,10R,12aR,14bS)-10-hydroxy-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: 915-32-2
• 化学式: C₃₁H₅₀O₃
• 分子量: 470.736
• InChiKey: YCBSMEKEDOHEQI-QNLMDLTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3α-hydroxyurs-12-en-28-oic acid methyl ester 在 chromium(VI) oxide 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以1 mg的产率得到3-Keto-熊果酸-28-甲酯
  参考文献：
  名称：

  Studies on the constituents of medicinal and related plants in sri lanka. I. New triterpenes from Hedyotis lawsoniae.

  摘要：

  从 Hedyotis lawsoniae 的树枝和树叶中分离出了三种新的三萜酸以及十六种已知的三萜酸。根据光谱证据，新化合物被确定为 3β、23-二羟基乌苏-12-烯-28-酸、3β、24-二羟基乌苏-12-烯-28-酸和 2α、3β、24-三羟基乌苏-12-烯-28-酸。

  DOI：

  10.1248/cpb.32.3906
• 作为产物：
  描述：

  熊果酸 在 aluminum (III) chloride 、 aluminum isopropoxide 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 17.33h， 生成 3α-hydroxyurs-12-en-28-oic acid methyl 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

• Huneck,S.; Snatzke,G., Chemische Berichte, 1965, vol. 98, p. 120 - 125
  作者：Huneck,S.、Snatzke,G.

  DOI：——

  日期：——
• 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.
• Studies on the constituents of medicinal and related plants in sri lanka. I. New triterpenes from Hedyotis lawsoniae.
  作者：TOHRU KIKUCHI、SATOKO MATSUDA、SHIGETOSHI KADOTA、YOSHIKO SAKAI、TSUNEO NAMBA、KAZUO WATANABE、RAN BANDA DISSANAYAKE DISSANAYAKE MUDIYANSELAGE

  DOI：10.1248/cpb.32.3906

  日期：——

  Three new triterpene acids were isolated from the twigs and leaves of Hedyotis lawsoniae, together with sixteen known ones. The new compounds were determined to be 3β, 23-dihydroxyurs-12-en-28-oic acid, 3β, 24-dihydroxyurs-12-en-28-oic acid, and 2α, 3β, 24-trihydroxyurs-12-en-28-oic acid on the basis of spectroscopic evidence.

  从 Hedyotis lawsoniae 的树枝和树叶中分离出了三种新的三萜酸以及十六种已知的三萜酸。根据光谱证据，新化合物被确定为 3β、23-二羟基乌苏-12-烯-28-酸、3β、24-二羟基乌苏-12-烯-28-酸和 2α、3β、24-三羟基乌苏-12-烯-28-酸。