N-(2-hydroxyethyl) 3β-hydroxy-11-oxo-18β-olean-12-en-30-oic acid amide

• 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: N-(2-hydroxyethyl) 3β-hydroxy-11-oxo-18β-olean-12-en-30-oic acid amide
• 英文别名: (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-N-(2-hydroxyethyl)-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-carboxamide
• 化学式: C₃₂H₅₁NO₄
• 分子量: 513.761
• InChiKey: CUHQXRIETJJGQE-XWEVEMRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甘草次酸 、 C.I.酸性橙108 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以32%的产率得到N-(2-hydroxyethyl) 3β-hydroxy-11-oxo-18β-olean-12-en-30-oic acid amide
  参考文献：
  名称：

  Synthesis of glycyrrhetinic acid derivatives for the treatment of metabolic diseases

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2009.10.036

文献信息

• Novel 18β-glycyrrhetinic acid analogues as potent and selective inhibitors of 11β-hydroxysteroid dehydrogenases
  作者：Xiangdong Su、Harshani Lawrence、Dharshini Ganeshapillai、Adrian Cruttenden、Atul Purohit、Michael J Reed、Nigel Vicker、Barry V.L Potter

  DOI：10.1016/j.bmc.2004.06.008

  日期：2004.8

  Extensive structural modifications to the 18beta-glycyrrhetinic acid template are described and their effects on the SAR of the 11beta-hydroxysteroid dehydrogenase isozymes type 1 and 2 from the rat are investigated. Isoform selective inhibitors have been discovered and compound 7 N-(2-hydroxyethyl)-3beta-hydroxy-11-oxo-18beta-olean-12-en-30-oic acid amide is highlighted as a very potent selective inhibitor of 11beta-hydroxysteroid dehydrogenase 2 with an IC50 = 4 pM. (C) 2004 Elsevier Ltd. All rights reserved.
• A novel 18β-glycyrrhetinic acid analogue as a potent and selective inhibitor of 11β-hydroxysteroid dehydrogenase 2
  作者：Nigel Vicker、Xiangdong Su、Harshani Lawrence、Adrian Cruttenden、Atul Purohit、Michael J. Reed、Barry V.L. Potter

  DOI：10.1016/j.bmcl.2004.03.107

  日期：2004.6

  Using 18beta-glycyrrhetinic acid as a template, the synthesis of a series of secondary amides at the 30-position is described and the effects of these modifications on the SAR of the 11beta-hydroxysteroid dehydrogenase isozymes type I and 2 from the rat are investigated. An isoform selective inhibitor has been discovered and compound 5, N-(2-hydroxyethyl)-3beta-hydroxy-11-oxo-18beta-olean-12-en-30-oic acid amide, is highlighted as a very potent and selective inhibitor of 11beta-hydroxysteroid dehydrogenase 2 with an IC50 = 4 pM. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.