(3β,18β,20β)-3-acetoxy-N-allyloxy-11-oxo-olean-12-en-29-amide | 1242695-94-8

• 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,18β,20β)-3-acetoxy-N-allyloxy-11-oxo-olean-12-en-29-amide
• 英文别名: (3S,18R,20S)-3-(acetyloxy)-N-(2-propen-1-yloxy)-11-oxo-olean-12-en-29-amide；[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-11-(prop-2-enoxycarbamoyl)-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl] acetate
• CAS: 1242695-94-8
• 化学式: C₃₅H₅₃NO₅
• 分子量: 567.81
• InChiKey: ZSIYINVYESEOPV-JOKULHESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3β,18β,20β)-3-acetoxy-N-allyloxy-11-oxo-olean-12-en-29-amide 在 甲醇 、 potassium hydroxide 作用下， 反应 48.0h， 以40%的产率得到(3β,18β,20β)-N-allyloxy-3-hydroxy-11-oxo-olean-12-en-29-amide
  参考文献：
  名称：

  Synthesis of novel 3-amino and 29-hydroxamic acid derivatives of glycyrrhetinic acid as selective 11β-hydroxysteroid dehydrogenase 2 inhibitors

  摘要：

  Glycyrrhetinic acid, the metabolite of the natural product glycyrrhizin, is a well known nonselective inhibitor of 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD) type 1 and type 2. Whereas inhibition of 11 beta-HSD1 is currently under consideration for treatment of metabolic diseases, such as obesity and diabetes, 11 beta-HSD2 inhibitors may find therapeutic applications in chronic inflammatory diseases and certain forms of cancer. So far, no selective 11 beta-HSD2 inhibitor has been developed and neither animal studies nor clinical trials have been reported based on 11 beta-HSD2 inhibition. Starting from the lead compound glycyrrhetinic acid, novel triterpene type derivatives were synthesized and analyzed for their biological activity against overexpressed human 11 beta-HSD1 and 11 beta-HSD2 in cell lysates. Several hydroxamic acid derivatives showed high selectivity for 11 beta-HSD2. The most potent and selective compound is active against human 11 beta-HSD2 in the low nanomolar range with a 350-fold selectivity over human 11 beta-HSD1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.046
• 作为产物：
  描述：

  3β-acetoxy-11-oxo-18β-olean-12-en-30-oyl chloride 、 O-烯丙基羟胺盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以44%的产率得到(3β,18β,20β)-3-acetoxy-N-allyloxy-11-oxo-olean-12-en-29-amide
  参考文献：
  名称：

  Synthesis of novel 3-amino and 29-hydroxamic acid derivatives of glycyrrhetinic acid as selective 11β-hydroxysteroid dehydrogenase 2 inhibitors

  摘要：

  Glycyrrhetinic acid, the metabolite of the natural product glycyrrhizin, is a well known nonselective inhibitor of 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD) type 1 and type 2. Whereas inhibition of 11 beta-HSD1 is currently under consideration for treatment of metabolic diseases, such as obesity and diabetes, 11 beta-HSD2 inhibitors may find therapeutic applications in chronic inflammatory diseases and certain forms of cancer. So far, no selective 11 beta-HSD2 inhibitor has been developed and neither animal studies nor clinical trials have been reported based on 11 beta-HSD2 inhibition. Starting from the lead compound glycyrrhetinic acid, novel triterpene type derivatives were synthesized and analyzed for their biological activity against overexpressed human 11 beta-HSD1 and 11 beta-HSD2 in cell lysates. Several hydroxamic acid derivatives showed high selectivity for 11 beta-HSD2. The most potent and selective compound is active against human 11 beta-HSD2 in the low nanomolar range with a 350-fold selectivity over human 11 beta-HSD1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.046

文献信息

• Synthesis of novel 3-amino and 29-hydroxamic acid derivatives of glycyrrhetinic acid as selective 11β-hydroxysteroid dehydrogenase 2 inhibitors
  作者：Christian Stanetty、Laszlo Czollner、Iris Koller、Priti Shah、Rawindra Gaware、Thierry Da Cunha、Alex Odermatt、Ulrich Jordis、Paul Kosma、Dirk Claßen-Houben

  DOI：10.1016/j.bmc.2010.08.046

  日期：2010.11

  Glycyrrhetinic acid, the metabolite of the natural product glycyrrhizin, is a well known nonselective inhibitor of 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD) type 1 and type 2. Whereas inhibition of 11 beta-HSD1 is currently under consideration for treatment of metabolic diseases, such as obesity and diabetes, 11 beta-HSD2 inhibitors may find therapeutic applications in chronic inflammatory diseases and certain forms of cancer. So far, no selective 11 beta-HSD2 inhibitor has been developed and neither animal studies nor clinical trials have been reported based on 11 beta-HSD2 inhibition. Starting from the lead compound glycyrrhetinic acid, novel triterpene type derivatives were synthesized and analyzed for their biological activity against overexpressed human 11 beta-HSD1 and 11 beta-HSD2 in cell lysates. Several hydroxamic acid derivatives showed high selectivity for 11 beta-HSD2. The most potent and selective compound is active against human 11 beta-HSD2 in the low nanomolar range with a 350-fold selectivity over human 11 beta-HSD1. (C) 2010 Elsevier Ltd. All rights reserved.