3,11-Dioxo-Δ¹²-oleanen-30-saeuremethylester-3-oxim | 13740-21-1

• 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: 3,11-Dioxo-Δ¹²-oleanen-30-saeuremethylester-3-oxim
• 英文别名: (18β,20β)-3-(hydroxyimino)-11-oxoolean-12-en-29-oic acid methyl ester；methyl 3-(hydroxyimino)-11-oxo-olean-12-en-30-oate；11-oxo-3-hydroxyimino-oleanen-(12)-oic acid-(30)-methyl ester；11-Oxo-3-hydroxyimino-oleanen-(12)-saeure-(30)-methylester；methyl (2S,4aS,6aR,6aS,6bR,8aR,12aS,14bR)-10-hydroxyimino-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,3,4,5,6,6a,7,8,8a,11,12,14b-dodecahydropicene-2-carboxylate
• CAS: 13740-21-1
• 化学式: C₃₁H₄₇NO₄
• 分子量: 497.718
• InChiKey: QQVLKKGLVXANOK-GJIZTULQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  76
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,11-Dioxo-Δ¹²-oleanen-30-saeuremethylester-3-oxim 在 盐酸 、 titanium(III) chloride 、 sodium acetate 、 borane tert-butylamine 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 20.0h， 生成 (2S,4aS,6aS,6bR,8aR,12aS,12bR,14bR)-10-amino-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-picene-2-carboxylic acid hydrochloride
  参考文献：
  名称：

  GLYCYRRHETINIC ACID DERIVATIVE AND USE THEREOF

  摘要：

  公开号：

  EP3075738B1
• 作为产物：
  描述：

  (3beta,20beta)-3-羟基-11-氧代-齐墩果-12-烯-29-酸甲酯 在 sodium dichromate 、 硫酸 、 羟胺 、 溶剂黄146 作用下， 生成 3,11-Dioxo-Δ¹²-oleanen-30-saeuremethylester-3-oxim
  参考文献：
  名称：

  Takeda, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1938, vol. 58, p. 731,737; dtsch. Ref. S. 194

  摘要：

  DOI：

文献信息

• Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives
  作者：René Csuk、Stefan Schwarz、Bianka Siewert、Ralph Kluge、Dieter Ströhl

  DOI：10.1016/j.ejmech.2011.08.038

  日期：2011.11

  Triterpenoic acids show many pharmacological effects, among them an antiinflammatory or an antitumor activity. One of these, glycyrrhetinic acid (1) is of interest because of its antitumor profile. Glycyrrhetinic acid is not only cytotoxic but also triggers apoptosis in various human tumor cell lines. To improve the cytotoxicity of parent 1 we set out to synthesize new derivatives of it-differing in structure and lipophilicity. These compounds were tested in a sulforhodamine B assay for cytotoxicity, and screened for their ability to induce apoptosis using an acridine orange/ethidium bromide assay and trypan blue staining. The most active compound, 34, a benzyl glycyrrhetinate holding an extra 3-N-(3-aminopropyl)glycyl substituent showed IC50 between 1.96 and 5.14 mu m for five human cancer cell lines and triggers apoptosis in 80% of the cells. (C) 2011 Elsevier Masson SAS. 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.
• Kurono, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1938, vol. 58, p. 770; dtsch. Ref. S. 220
  作者：Kurono

  DOI：——

  日期：——