(3beta,20alpha)-3-羟基-11-氧代齐墩果-12-烯-29-酸 | 10379-72-3

• 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
• 中文名称: (3beta,20alpha)-3-羟基-11-氧代齐墩果-12-烯-29-酸
• 英文名称: glycyrrhetinic acid
• 英文别名: (3beta,20alpha)-3-Hydroxy-11-oxoolean-12-en-29-oic acid；(2R,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-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: 10379-72-3
• 化学式: C₃₀H₄₆O₄
• 分子量: 470.693
• InChiKey: MPDGHEJMBKOTSU-IDZWEYSVSA-N

物化性质

• 熔点：
  330 °C(Solv: acetic acid (64-19-7))
• 沸点：
  588.3±50.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  34
• 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：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3beta,20alpha)-3-羟基-11-氧代齐墩果-12-烯-29-酸 在 chloropyridinecobaloxime(III) 、 2,7-Dimethyl-9-phenyl-acridin 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 36.0h， 以80%的产率得到C₂₉H₄₄O₂
  参考文献：
  名称：

  羧酸和生物质的光催化化学酶相容脱氢脱羧合成烯烃

  摘要：

  通过温和的化学选择性催化方法将可再生生物质和生物衍生化学品直接转化为有价值的合成中间体，用于有机合成和材料科学应用，在很大程度上仍然难以捉摸。通过利用以前无法实现的反应性和选择性模式，开发与酶促反应兼容的人工催化系统为这一持久挑战提供了协同解决方案。我们在此报告了一种双催化脱氢脱羧反应，该反应是通过光诱导吖啶催化的 O-H 氢原子转移 (HAT) 和钴肟催化的 C-H-HAT 过程的交叉实现的。该反应由容易获得的羧酸产生多种烯烃。

  DOI：

  10.1021/acscatal.9b02951

文献信息

• Acridine Photocatalysis: Insights into the Mechanism and Development of a Dual-Catalytic Direct Decarboxylative Conjugate Addition
  作者：Hang T. Dang、Graham C. Haug、Vu T. Nguyen、Ngan T. H. Vuong、Viet D. Nguyen、Hadi D. Arman、Oleg V. Larionov

  DOI：10.1021/acscatal.0c03440

  日期：2020.10.2

  Conjugate addition is one of the most synthetically useful carbon–carbon bond-forming reactions; however, reactive carbon nucleophiles are typically required to effect the addition. Radical conjugate addition provides an avenue for replacing reactive nucleophiles with convenient radical precursors. Carboxylic acids can serve as simple and stable radical precursors by way of decarboxylation, but activation

  共轭加成是合成中最有用的碳-碳键形成反应之一；然而，通常需要反应性碳亲核试剂来实现加成。自由基共轭加成提供了一种用方便的自由基前体取代反应性亲核试剂的途径。羧酸可以通过脱羧作用作为简单而稳定的自由基前体，但通常需要活化成反应性酯以促进具有挑战性的脱羧作用。在这里，我们报告了多种羧酸的直接双催化脱羧自由基共轭加成，不需要酸预活化，并且通过可见光驱动的吖啶光催化与有效的铜催化循环相结合来实现。
• Synthesis of triterpenoid acylates: Effective reproduction inhibitors of influenza A (H1N1) and papilloma viruses
  作者：O. B. Kazakova、N. I. Medvedeva、I. P. Baikova、G. A. Tolstikov、T. V. Lopatina、M. S. Yunusov、L. Zaprutko

  DOI：10.1134/s1068162010060142

  日期：2010.11

  The synthesis of a new group of triterpenoid acylates has been conducted on the basis of oleanolic, glycyrrhetic, and ursolic acids and betulin. 28-ortho-Methoxycynnamoylbetulin has been demonstrated to possess high activity against the influenza type A (H1N1) virus with the selectivity index SI > 100 while studying the activity of the synthesized compounds in relation to the reproduction of viral

  以齐墩果酸、甘草次酸、熊果酸和桦木脑为基础合成了一组新的三萜酰化物。在研究合成化合物与呼吸道感染病毒病原体繁殖相关的活性时，28-ortho-Methoxycynnamoylbetulin 已被证明对甲型流感 (H1N1) 病毒具有高活性，选择性指数 SI > 100。3,28-二烟酰桦木素对乳头状瘤病毒（HPV-11 株）具有高活性，选择性指数 SI 35。
• Synthesis and biological evaluation of T-OA analogues as the cytotoxic agents
  作者：Kuo Xu、Xin Xu、Fuhao Chu、Mina Wang、Penglong Wang、Guoliang Li、Jixiang Song、Yuzhong Zhang、Haimin Lei

  DOI：10.1007/s11164-014-1737-z

  日期：2015.9

  The lead compound T-OA, 3β-hydroxyolean-12-en-28-oic acid-(3,5,6-trimethylpyrazine-2-yl) methyl ester, which exhibited promising anticancer effects in vitro and in vivo, has previously been reported. According to the structural features, a series of novel T-OA analogues were synthesized via amino condensation reaction. These analogues’ cytotoxic activities were evaluated on five cancer cell lines (Bel-7402, HepG-2, HT-29, Hela, BGC-823) and hepatic stellate cell line (HSC-6). Among the candidates, compounds 8 and 16 showed promising effects; 3β-hydroxy-lup-20(29)-ene-28-oic acid-(3,5,6-trimethylpyrazin-2-yl) methyl amine (16) even possessed superior bioactivities to positive drugs (cisplatin and ursolic acid), which was worthy of further study. In addition, structure–activity relationships and Clog P values of T-OA analogues were briefly discussed.

  先导化合物T-OA，即3β-羟基烯-12-烯-28-酸-(3,5,6-三甲基吡嗪-2-基)甲酯，已被报道在体外和体内显示出良好的抗癌效果。根据结构特征，通过氨基缩合反应合成了一系列新的T-OA类类似物。这些类似物在五种癌细胞系（Bel-7402、HepG-2、HT-29、Hela、BGC-823）和肝星形细胞系（HSC-6）上评估了其细胞毒活性。在候选化合物中，化合物8和16显示出良好的效果；3β-羟基-露皮-20(29)-烯-28-酸-(3,5,6-三甲基吡嗪-2-基)甲胺（16）甚至具有优于阳性药物（顺铂和熊果酸）的生物活性，值得进一步研究。此外，简要讨论了T-OA类类似物的结构-活性关系和Clog P值。
• Compositions and methods for treatment of prostate carcinoma
  申请人：Pellficure Pharmaceuticals, Inc.

  公开号：US10093620B2

  公开（公告）日：2018-10-09

  Disclosed herein are 1,4-naphthoquinone analogs, pharmaceutical compositions that include one or more of such 1,4-naphthoquinone analogs, and methods of treating and/or ameliorating diseases and/or conditions associated with a cancer, such as prostate cancer with such 1,4-naphthoquinone analogs. Also included are combination therapies wherein a 1,4-naphthoquinone analog disclosed herein, and a hormone therapy agent are provided to a subject suffering from a condition such as cancer.

  本文公开了1,4-萘醌类似物、包括一种或多种此类1,4-萘醌类似物的药物组合物，以及用此类1,4-萘醌类似物治疗和/或改善与癌症（如前列腺癌）相关的疾病和/或病症的方法。还包括组合疗法，其中向患有癌症等疾病的受试者提供本文公开的 1,4-萘醌类似物和激素治疗剂。
• Synthesis, modification, and antimicrobial activity of the N-methylpiperazinyl amides of triterpenic acids
  作者：O. B. Kazakova、G. V. Giniyatullina、G. A. Tolstikov、N. I. Medvedeva、T. M. Utkina、O. L. Kartashova

  DOI：10.1134/s1068162010030155

  日期：2010.5

  N-methylpyperazinyl amides of betulinic, platanic, glycyrrhetic, oleanolic, ursolic, and moronic acids were synthesized and modified. Betulin and betulonic acid showed antimicrobial activity against Staphylococcus aureus at a concentration of 90 mg/ml, and betulin manifested a bacteriostatic effect against Klebsiella pneumoniae at a concentration of 60 mg/ml. Among the studied N-methylpyperazinyl amides, the highest activity against S. aureus was observed for a betulonic acid derivative.