11-oxo-18β-olean-12-en-30-oic acid | 17063-98-8

• 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: 11-oxo-18β-olean-12-en-30-oic acid
• 英文别名: 3-deoxyglycyrrhetic acid；11-oxo-olean-12-en-30-oic acid；(2S,4aS,6aR,6aS,6bR,8aS,12aS,14bR)-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-carboxylic acid
• CAS: 17063-98-8
• 化学式: C₃₀H₄₆O₃
• 分子量: 454.693
• InChiKey: AADDJCZOXWMWBH-ICSARBIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11-oxo-18β-olean-12-en-30-oic acid 在 platinum(IV) oxide 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 17.0h， 以84.8%的产率得到18β-olean-12-en-30-oic acid
  参考文献：
  名称：

  Glycyrrhetinic acid derivatives as potent inhibitors of Na+, K+-ATPase. Synthesis and structure-activity relationships

  摘要：

  A series of ring A-modified GA derivatives (26 compounds) has been systematically synthesized and the structure-activity relationship investigated for inhibition of canine kidney Na+, K+-ATPase in vitro. The most potent inhibitory activity was found with a group of the 3-deoxygenated derivatives including 5, 6, 9, 10 and 11. The high inhibition may be closely related to the hydrophobic character of the A-ring of these compounds. This finding suggests that the ATP-binding site at the active center of the enzyme is located in a hydrophobic environment.

  DOI：

  10.1016/0223-5234(92)90147-s
• 作为产物：
  描述：

  (3beta,20beta)-3-羟基-11-氧代-齐墩果-12-烯-29-酸甲酯 在 偶氮二异丁腈 、 三正丁基氢锡 、 lithium iodide 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 7.0h， 生成 11-oxo-18β-olean-12-en-30-oic acid
  参考文献：
  名称：

  Glycyrrhetinic acid derivatives as potent inhibitors of Na+, K+-ATPase. Synthesis and structure-activity relationships

  摘要：

  A series of ring A-modified GA derivatives (26 compounds) has been systematically synthesized and the structure-activity relationship investigated for inhibition of canine kidney Na+, K+-ATPase in vitro. The most potent inhibitory activity was found with a group of the 3-deoxygenated derivatives including 5, 6, 9, 10 and 11. The high inhibition may be closely related to the hydrophobic character of the A-ring of these compounds. This finding suggests that the ATP-binding site at the active center of the enzyme is located in a hydrophobic environment.

  DOI：

  10.1016/0223-5234(92)90147-s

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：10.1515/znb-2011-0513

  日期：2011.5.1

  The pentacyclic triterpene glycyrrhetinic acid is an interesting natural product exhibiting various biological activities. Especially its ability to induce apoptosis in tumor cells is of high scientific interest. In this study we altered the lipophilicity in ring A by derivatization at positions C-2 and C-3. The consequences of these variations on the cytotoxicity were investigated applying a colorimetric sulforhodamine B assay using 8 different human tumor cell lines. An acridine orange/ethidium bromide (AO/EB) test and a trypan blue test were used to determine the extent of apoptotic activity of some of these compounds

  五环三萜甘草酸是一种具有多种生物活性的有趣天然产物。特别是它在诱导肿瘤细胞凋亡方面的能力具有很高的科学意义。在这项研究中，我们通过在C-2和C-3位置进行衍生化改变环A的亲脂性。通过应用8种不同的人类肿瘤细胞系进行的一种比色法苏丹红B检测，研究了这些变化对细胞毒性的影响。使用吖啶橙/溴化乙锭（AO/EB）试验和尝试蓝试验来确定其中一些化合物的凋亡活性程度。
• USE OF GLYCYRRHETINIC ACID, GLYCYRRHIZIC ACID AND RELATED COMPOUNDS FOR MITIGATION AND/OR TREATMENT OF PNEUMONITIS/PNEUMONIA/PULMONARY FIBROSIS INDUCED BY VIRUS INFECTION AND/OR BY CHEMICAL OR BIOLOGICAL AGENTS
  申请人：ZHANG Lurong

  公开号：US20210244691A1

  公开（公告）日：2021-08-12

  The present invention pertains to novel uses of glycyrrhetinic acid (GA), glycyrrhizic acid (GR) and related compounds for mitigation and/or treatment of pneumonitis/pneumonia/pulmonary fibrosis induced by various chemicals/bioagents and/or pathogens, such as anti-cancer therapies and/or virus. Also embodied are therapeutic uses of prodrugs, metabolites, derivatives (e.g., acids, esters and ethers), and salts of glycyrrhetinic acid (GA) and glycyrrhizic acid (GR) in a form of drugs, health products, foods or food additives.
• [EN] ANTIVIRAL TRITERPENE DERIVATIVES<br/>[FR] DÉRIVÉS DE TRITERPÈNE ANTIVIRAUX
  申请人：SAVIRA PHARMACEUTICALS GMBH

  公开号：WO2010139692A2

  公开（公告）日：2010-12-09

  The present invention encompasses novel triterpene compounds of general Formula (I) wherein RN1, RN2, R11a, R11b, R4, R17, R19 and R20 are defined as in claim 1, which exhibit an antiviral effect and are therefore suitable for the treatment of diseases related thereto and the use thereof for preparing a medicament having the above-mentioned properties.