(3β,18β,20β)-3-(methoxyamino)-11-oxoolean-12-en-29-oic acid diphenylmethyl ester | 1207976-45-1

• 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-(methoxyamino)-11-oxoolean-12-en-29-oic acid diphenylmethyl ester
• 英文别名: (3S,18R,20S)-3-(N-methoxamino)-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester
• CAS: 1207976-45-1
• 化学式: C₄₄H₅₉NO₄
• 分子量: 665.957
• InChiKey: SZIJOIGNBBJPEX-SLEIDBJYSA-N

物化性质

• 沸点：
  699.3±65.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.82
• 重原子数：
  49.0
• 可旋转键数：
  6.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3β,18β,20β)-3-(methoxyamino)-11-oxoolean-12-en-29-oic acid diphenylmethyl ester 在 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以85.1%的产率得到(3β,18β,20β)-3-methoxyamino-11-oxo-olean-12-en-29-oic acid
  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：

  (18β,20β)-3-(methoxyimino)-11-oxoolean-12-en-29-oic acid diphenylmethyl ester 在 盐酸 、 硼烷-叔丁基胺 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 以42%的产率得到(3β,18β,20β)-3-(methoxyamino)-11-oxoolean-12-en-29-oic acid diphenylmethyl ester
  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

• [EN] ANTIVIRAL TRITERPENE DERIVATIVES<br/>[FR] DÉRIVÉS DE TRITERPÈNE ANTIVIRAUX
  申请人：SAVIRA PHARMACEUTICALS GMBH

  公开号：WO2010139692A3

  公开（公告）日：2011-03-10