(18β,20β)-3-(hydroxyimino)-11-oxoolean-12-en-29-oic acid diphenylmethyl ester | 1207976-38-2

• 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: (18β,20β)-3-(hydroxyimino)-11-oxoolean-12-en-29-oic acid diphenylmethyl ester
• 英文别名: (3β,18β,20β)-3-(hydroxyimino)-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester
• CAS: 1207976-38-2
• 化学式: C₄₃H₅₅NO₄
• 分子量: 649.914
• InChiKey: PBLWOGSTJBLFEU-NQHIZHEYSA-N

物化性质

• 熔点：
  215-216 °C
• 沸点：
  719.2±60.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.13
• 重原子数：
  48.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  75.96
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (18β,20β)-3-(hydroxyimino)-11-oxoolean-12-en-29-oic acid diphenylmethyl ester 在 palladium 10% on activated carbon 氯化亚砜 、 五氯化磷 、 氢气 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 20.0 ℃ 、200.0 kPa 条件下， 反应 15.5h， 生成
  参考文献：
  名称：

  [EN] NOVEL TRITERPENE DERIVATIVES
  [FR] NOUVEAUX DÉRIVÉS TRITERPÉNIQUES

  摘要：

  本发明涵盖了一般式（I）中R11a到R30和X的化合物，其中如权利要求书中所定义的，适用于治疗和/或预防慢性炎症性疾病、自身免疫疾病、皮肤疾病、骨疾病、代谢性疾病、传染病和癌症。

  公开号：

  WO2012020019A1
• 作为产物：
  描述：

  甘草次酸 在 吡啶 、 盐酸羟胺 、 pyridinium chlorochromate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (18β,20β)-3-(hydroxyimino)-11-oxoolean-12-en-29-oic acid diphenylmethyl ester
  参考文献：
  名称：

  [EN] NOVEL TRITERPENE DERIVATIVES
  [FR] NOUVEAUX DÉRIVÉS TRITERPÉNIQUES

  摘要：

  本发明涵盖了一般式（I）中R11a到R30和X的化合物，其中如权利要求书中所定义的，适用于治疗和/或预防慢性炎症性疾病、自身免疫疾病、皮肤疾病、骨疾病、代谢性疾病、传染病和癌症。

  公开号：

  WO2012020019A1

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.
• 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.