methyl (1α,4β,9α)-2,3-dihydro-1,9-peroxo-11-oxo-urs-12-en-24-oate | 1246431-64-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1α,4β,9α)-2,3-dihydro-1,9-peroxo-11-oxo-urs-12-en-24-oate
• 英文别名: methyl 2,3-dihydro-1α,9α-peroxo-11-oxo-urs-12-en-24-oate；methyl (1R,5R,6S,7R,10R,13R,14S,17R,18S,21S,24R)-6,7,10,13,14,18,24-heptamethyl-2-oxo-22,23-dioxahexacyclo[15.6.1.01,14.04,13.05,10.021,24]tetracosa-3,19-diene-18-carboxylate
• CAS: 1246431-64-0
• 化学式: C₃₁H₄₄O₅
• 分子量: 496.687
• InChiKey: QWFCRIPBNBFZMV-BJUHLLCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙酰基-11-酮基-beta-乳香酸 在 3,3-二甲基谷酰胺 、 N-羟基邻苯二甲酰亚胺 、 sodium dichromate dihydrate 、 氧气 、 caesium carbonate 、 三苯基膦 、 sodium hydroxide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 为溶剂， 反应 54.5h， 生成 methyl (1α,4β,9α)-2,3-dihydro-1,9-peroxo-11-oxo-urs-12-en-24-oate
  参考文献：
  名称：

  Oxidative and reductive transformations of 11-keto-β-boswellic acid

  摘要：

  Extraction of frankincense-a fragrant resin obtained from plants of the genus Boswellia followed by an oxidation furnished high yields of (313) 3-O-acetyl-11-keto-beta-boswellic acid (beta-AKBA), a valuable starting material for accessing boswellic acid derivatives. Boswellic acids are fascinating triterpenoic acids that exhibit different biological activities. However, their biological potential, as well as that of their derivatives, remained unexploited due to their limited availability. In this study we were able to prepare derivatives of 11-keto-beta-boswellic acid in good to excellent yields by oxidative and reductive transformations mainly in rings A and C of the triterpenoid skeleton. Among other transformations, a highly cytotoxic endoperoxide was obtained in excellent yields. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.01.062

文献信息

• Synthesis of an antitumor active endoperoxide from 11-keto-β-boswellic acid
  作者：René Csuk、Anja Niesen-Barthel、Alexander Barthel、Ralph Kluge、Dieter Ströhl

  DOI：10.1016/j.ejmech.2010.05.036

  日期：2010.9

  An endoperoxide was synthesized starting from 11-keto-beta-boswellic acid and screened for antitumor activity in a panel of 15 human cancer cell lines by an SRB assay. The compound induces apoptosis and shows an average IC(50) value of 0.4-4.5 mu M. (C) 2010 Elsevier Masson SAS. All rights reserved.