Acetic acid (3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-azidocarbonyl-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-3-yl ester | 58307-68-9

• 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: Acetic acid (3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-azidocarbonyl-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-3-yl ester
• CAS: 58307-68-9
• 化学式: C₃₂H₄₇N₃O₄
• 分子量: 537.743
• InChiKey: SWQYYSDURUMIFC-XWEVEMRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.74
• 重原子数：
  39.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  109.2
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-azidocarbonyl-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-3-yl ester 在 氨 作用下， 以 氯仿 为溶剂， 反应 12.25h， 生成 (3β,18β,20β)-N-[-3-(acetoxy)-11-oxo-30-norolean-12-en-20-yl]urea
  参考文献：
  名称：

  Synthesis of new glycyrrhetinic acid derived ring A azepanone, 29-urea and 29-hydroxamic acid derivatives 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. Recently, we published a series of hydroxamic acid derivatives of glycyrrhetinic acid showing 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. Starting from the lead compounds glycyrrhetinic acid and the hydroxamic acid derivatives, 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. Here we describe novel 29-urea- and 29-hydroxamic acid derivatives of glycyrrhetinic acid as well as derivatives with the Beckman rearrangement of the 3-oxime to a seven-membered ring, and the rearrangement of the C-ring from 11-keto-12-ene to 12-keto-9(11)-ene. The combination of modifications on different positions led to compounds comprising further improved selective inhibition of 11 beta-HSD2 in the lower nanomolar range with up to 3600-fold selectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.005
• 作为产物：
  描述：

  在 sodium azide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 Acetic acid (3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-azidocarbonyl-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-3-yl ester
  参考文献：
  名称：

  Ibrahim, Yehia Abdu; Hanna, Atef G.; Elgamal, M. Hani A., Pakistan Journal of Scientific and Industrial Research, 1995, vol. 38, # 3-4, p. 101 - 107

  摘要：

  DOI：

文献信息

• Aufbau eines Tetraens aus 18β-Glycyrrhetinsäure
  作者：C. H. Brieskorn、V. Beer

  DOI：10.1002/ardp.19753081109

  日期：——

  Ausgehend von 18β‐Glycyrrhetinsäure werden 30Nor‐11 α‐methyl‐3β,11β‐dihydroxyoleantrien (12, 18, 20) (5) und 30Nor‐11methyl‐3β‐hydroxyoleantetraen (9, (11), 12, 18, 20) (7) hergestellt.

  从 18β-甘草次酸、30Nor-11 α-methyl-3β、11β-dihydroxyoleanttriene (12, 18, 20) (5) 和 30Nor-11methyl-3β-hydroxyoleantetraene (9, (11), 12, 18, 20) 开始(7) 制造。