11-oxo-18β-oleana-2,12-dien-30-oic acid | 37828-46-9

• 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-oleana-2,12-dien-30-oic acid
• 英文别名: 2,3-ene-18β-glycyrrhetic acid；2-ene-glycyrrhetinic acid；11-oxo-18β-olean-2,12-dien-29-oic acid；11-oxo-olean-2,12-dien-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,12,14b-decahydro-1H-picene-2-carboxylic acid
• CAS: 37828-46-9
• 化学式: C₃₀H₄₄O₃
• 分子量: 452.678
• InChiKey: PCERXXRBTLLREU-ICSARBIRSA-N

物化性质

• 熔点：
  292-295 °C
• 沸点：
  555.9±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 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-oleana-2,12-dien-30-oic acid 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以284 mg的产率得到2,3-epoxy-18β-glycyrrhetic acid
  参考文献：
  名称：

  2,3-双羟基甘草次酸用于制备治疗病毒性乙肝药物的用途

  摘要：

  本发明涉及2,3‑双羟基甘草次酸用于制备治疗病毒性乙肝药物的用途。具体而言，本发明提供了式(1)化合物，即2β,3α‑二羟基‑11‑羰基齐墩果烷‑12‑烯‑30‑羧酸，在制备防治乙型肝炎病毒感染疾病的药物中的应用。式(1)化合物在66.75微克/毫升浓度下其抑制HBeAg分泌的强度为100微克/毫升的拉米呋啶的1.79倍；该浓度下其对HBV‑DNA复制显示出95.3％的抑制率，高于100微克/毫升的阳性对照拉米呋啶对HBV‑DNA复制的抑制活性。以上表明该2,3‑双羟基甘草次酸可预期用于制备治疗乙型肝炎病毒感染疾病之非核苷类药物的用途，具体而言，该化合物具有用于制备HBV‑DNA、HBeAg抑制剂的用途，且其制备方法步骤简单、成本低，且原料来源广泛，容易进行产业化生产。

  公开号：

  CN111904963A
• 作为产物：
  描述：

  3β-methylsulfonyl-11-carbonyloleanorane-12-ene-30-oic acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以44%的产率得到11-oxo-18β-oleana-2,12-dien-30-oic acid
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Ring A-modified Glycyrrhetinic Acid Derivatives

  摘要：

  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。

  DOI：

  10.1515/znb-2011-0513

文献信息

• Two new compounds from biotransformation of glycyrrhetinic acid
  作者：Zehao Xie、Xinxin Gu、Aman Dekebo、Shaozhong Wei、Xuebo Hu

  DOI：10.1080/14786419.2024.2306918

  日期：——

  Glycyrrhetinic acid may undergo biotransformation to obtain derivatives with stronger pharmacological activity and fewer side effects. This study used 19 fungi to biotransform glycyrrhetinic acid a...

  甘草次酸可经过生物转化，得到药理活性更强、副作用更少的衍生物。这项研究使用 19 种真菌来生物转化甘草次酸...
• Synthesis and crystal structures of ring A modified glycyrrhetinic acid derivatives derived from 2,3-oxirane and 2,3-thiirane intermediates
  作者：Hassan Amer、Kurt Mereiter、Christian Stanetty、Andreas Hofinger、Laszlo Czollner、Igor Beseda、Ulrich Jordis、Bernhard Kueenburg、Dirk Claßen-Houben、Paul Kosma

  DOI：10.1016/j.tet.2010.03.098

  日期：2010.6

  A general method for the introduction of thiol groups at positions 1, 2, and 3 of glycyrrhetinic acid has been developed starting from a protected 2 alpha,3 alpha-oxido-derivative. Conversion into the corresponding 2 beta,3 beta-epithio-derivative was followed by ring-opening leading to either 2- or 3-substituted thio derivatives. Conversely, 3 alpha-configured allylic alcohol intermediates derived from the 2,3-epoxide provided efficient access to both diastereoisomeric 3-thio derivatives as well as 1 alpha-thio derivatives. The stereochemistry of the newly formed stereogenic centers was rigorously proven using X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.
• Anti-tumor-promoter activity of modified glycyrrhetinic acid derivatives. Synthesis and structure-activity relationships
  作者：T Terasawa、T Okada、H Nishino

  DOI：10.1016/0223-5234(92)90088-i

  日期：1992.10

  A series of modified derivatives of 18alpha- and 18beta-glycyrrhetinic acid was systematically synthesized and their structure-activity relationships investigated for inhibition of the promoter activity of 12-O-tetradecanoylphorbol-13-acetate in vitro. Increased hydrophobicity in the A-ring moiety and the presence of an 11-oxo function were shown to be important for the high inhibition. Replacement of the carboxy to the hydroxymethyl group at the 20-position also enhanced the inhibitory activity.
• Glycyrrhetinic acid derivatives as potent inhibitors of Na+, K+-ATPase. Synthesis and structure-activity relationships
  作者：T Terasawa、T Okada、T Hara、K Itoh

  DOI：10.1016/0223-5234(92)90147-s

  日期：1992.6

  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.