(3α,18β,20β)-3-hydroxy-11-oxoolean-12-en-29-oic acid methyl ester | 21857-94-3

• 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,18β,20β)-3-hydroxy-11-oxoolean-12-en-29-oic acid methyl ester
• 英文别名: methyl (2S,4aS,6aR,6aS,6bR,8aR,10R,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate
• CAS: 21857-94-3
• 化学式: C₃₁H₄₈O₄
• 分子量: 484.72
• InChiKey: RMIVRCBSQPCSCQ-RQJBKSHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3α,18β,20β)-3-hydroxy-11-oxoolean-12-en-29-oic acid methyl ester 在 lithium iodide 作用下， 以 various solvent(s) 为溶剂， 反应 3.0h， 生成 3α-hydroxyglycyrrhetic acid
  参考文献：
  名称：

  Glycyrrhetinic acid derivatives as potent inhibitors of Na+, K+-ATPase. Synthesis and structure-activity relationships

  摘要：

  A series of ring A-modified GA derivatives (26 compounds) has been systematically synthesized and the structure-activity relationship investigated for inhibition of canine kidney Na+, K+-ATPase in vitro. The most potent inhibitory activity was found with a group of the 3-deoxygenated derivatives including 5, 6, 9, 10 and 11. The high inhibition may be closely related to the hydrophobic character of the A-ring of these compounds. This finding suggests that the ATP-binding site at the active center of the enzyme is located in a hydrophobic environment.

  DOI：

  10.1016/0223-5234(92)90147-s
• 作为产物：
  描述：

  (3beta,20beta)-3-羟基-11-氧代-齐墩果-12-烯-29-酸甲酯 在 偶氮二异丁腈 、 氢溴酸 、 三正丁基氢锡 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 苯 为溶剂， 反应 6.17h， 生成 (3α,18β,20β)-3-hydroxy-11-oxoolean-12-en-29-oic acid methyl ester
  参考文献：
  名称：

  Glycyrrhetinic acid derivatives as potent inhibitors of Na+, K+-ATPase. Synthesis and structure-activity relationships

  摘要：

  A series of ring A-modified GA derivatives (26 compounds) has been systematically synthesized and the structure-activity relationship investigated for inhibition of canine kidney Na+, K+-ATPase in vitro. The most potent inhibitory activity was found with a group of the 3-deoxygenated derivatives including 5, 6, 9, 10 and 11. The high inhibition may be closely related to the hydrophobic character of the A-ring of these compounds. This finding suggests that the ATP-binding site at the active center of the enzyme is located in a hydrophobic environment.

  DOI：

  10.1016/0223-5234(92)90147-s

文献信息

• Synthesis of glycyrrhetinic acid derivatives for the treatment of metabolic diseases
  作者：Igor Beseda、Laszlo Czollner、Priti S. Shah、Rupesh Khunt、Rawindra Gaware、Paul Kosma、Christian Stanetty、Maria Carmen del Ruiz-Ruiz、Hassan Amer、Kurt Mereiter、Thierry Da Cunha、Alex Odermatt、Dirk Claßen-Houben、Ulrich Jordis

  DOI：10.1016/j.bmc.2009.10.036

  日期：2010.1

  The effect of glycyrrhetinic acid (GA) and GA-derivatives towards 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD) was investigated. Novel compounds with modi. cations at positions C-3, C-11 and C-29 of the GA skeleton were prepared. Single crystal X-ray diffraction data of selected substances are reported and discussed. (C) 2009 Elsevier Ltd. All rights reserved.