glycyrrhetinic acid

• 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: glycyrrhetinic acid
• 英文别名: GA；(2S,4aS,6aR,6aS,6bR,8aR,10S,12aS)-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
• 化学式: C₃₀H₄₆O₄
• 分子量: 470.693
• InChiKey: MPDGHEJMBKOTSU-JINNPRJSSA-N

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：

  glycyrrhetinic acid 在 4-二甲氨基吡啶 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 9.5h， 生成
  参考文献：
  名称：

  靶向肝细胞癌的羰基钴复合物的合成，毒性和抗肿瘤活性。

  摘要：

  根据我们先前的研究，一系列靶向肝细胞癌的复合物，[R-甘草次酸-CH 2 C 2 H- [Co 2（CO）6 ]（R = H，1 ; R = NSAIDs-COOH，2 – 4 ; R =芳族酸，5 - 7 ; R =氨基酸，8 - 10），合成。测试表明它们是缓慢的一氧化碳释放剂。以HeLa，A549，HT-29，SMMC7721和HepG2细胞为模型，首先评估了它们对肿瘤细胞增殖的活性。结果数据显示，所有复合物均对HepG2和SMMC-7721肝癌细胞及其IC表现出良好的抗增殖活性。50个值在10.07-66.06 µM的范围内；与顺铂（DDP）相比，它们在相同条件下的活性相当甚至更好。其中，配合物3，4，6和9对HepG2和SMMC-7721的细胞系比其他细胞系显示出较高的抗增殖活性。为了确认这些进一步配合物具有选择性的肝细胞，复合物的喉管3，4，6和9通过HepG2，HT-29，A

  DOI：

  10.1016/j.bmc.2019.115071
• 作为产物：
  描述：

  在 β-glucuronidase from Aspergillus ustus Li-62 作用下， 以 aq. acetate buffer 为溶剂， 生成 glycyrrhetinic acid
  参考文献：
  名称：

  Properties and structures of β-glucuronidases with different transformation types of glycyrrhizin

  摘要：

  分析了具有不同 GL 水解类型的三种真菌 β-葡萄糖醛酸酶的底物识别机制。

  DOI：

  10.1039/c5ra11484e

文献信息

• The preparation of some derivatives of glycyrrhetic acid and oleanolic acid
  作者：P D G DEAN、T G HALSALL、M W WHITEHOUSE

  DOI：10.1111/j.2042-7158.1967.tb08011.x

  日期：2011.4.12

  Some new derivatives of glycyrrhetic acid and oleanolic acid were prepared and characterized. Various combinations of the modified and normal functional groups were synthesized as required for a separate study of the uncoupling activities of glycyrrhetic acid and oleanolic acid. The hydroxyl functions of these two acids were modified to β-carboxypropionyl, acetyl and β-methoxycarbonylpropionyl esters. The carboxyl function of glycyrrhetic acid was converted to amide, p-amidobenzoic acid, o-amidobenzoic acid and the glycine conjugate of the acid. 11-Deoxy (glycyrrhetic acid) and 9,11-dehydro-11-deoxo (from both acids) analogues were prepared. 11-Oxo analogues of oleanolic acid were synthesized as well as the methyl esters.

  摘要：制备和表征了一些甘草酸和齐墩果酸的新衍生物。根据需要合成了修改和正常官能团的各种组合，以便对甘草酸和齐墩果酸的解耦活性进行单独研究。这两种酸的羟基功能被修改为β-羧丙酰基、乙酰基和β-甲氧羰基丙酰酯。甘草酸的羧基功能转化为酰胺、对-氨基苯甲酸、邻-氨基苯甲酸和该酸的甘氨酸结合物。制备了11-去氧（甘草酸）和9,11-脱氢-11-去氧（来自两种酸）的类似物。合成了齐墩果酸的11-酮类似物以及甲酯。
• A环多氧化取代甘草次酸衍生物及其制备方 法和用途
  申请人：贵州省中国科学院天然产物化学重点实验室

  公开号：CN103923158B

  公开（公告）日：2017-03-29

  本发明公开了A环多氧化取代甘草次酸衍生物及其制备方法和用途，该化合物的通式如下，其中R1选自羰基或羟基；R2、R3均为羟基或R2与R3之间是环氧基；R4选自‑COOH、‑COOR1、‑CONH2、‑CONHR1、‑CONR1R2；R1、R2均选自含有1‑15个碳原子的烷基、取代或未取代的苯基、取代或未取代的苯烷基，R1与R2可相同或不同；Y为CH2或C＝O；18位的氢为α或β构型；R1、R2、R3为羟基时，其羟基取代构型各为α或β构型。本发明所提供的结构新颖的化合物及其盐具有较强的保肝活性，可用于保肝药物的制备；并具有抗菌或抗烟草花叶病毒的用途，在医药和农药领域均具有良好的应用前景。
• Synthesis and Biological Evaluation of New Ligustrazine Derivatives as Anti-Tumor Agents
  作者：Penglong Wang、Gaimei She、Yanan Yang、Qiang Li、Honggui Zhang、Jie Liu、Yinqiu Cao、Xin Xu、Haimin Lei

  DOI：10.3390/molecules17054972

  日期：——

  To discover new anti-cancer agents with multi-effect and low toxicity, a series of ligustrazine derivatives were synthesized using several effective anti-tumor ingredients of Shiquandabu Wan as starting materials. Our idea was enlightened by the “combination principle” in drug discovery. The ligustrazine derivatives’ anti-tumor activities were evaluated on the HCT-8, Bel-7402, BGC-823, A-549 and A2780

  为发现新的多效低毒抗癌药物，以十全大补丸的几种有效抗肿瘤成分为原料合成了川芎嗪系列衍生物。我们的想法受到药物发现中的“组合原则”的启发。在 HCT-8、Bel-7402、BGC-823、A-549 和 A2780 人类癌细胞系上评估了川芎嗪衍生物的抗肿瘤活性。此外，通过小鸡绒毛尿囊膜（CAM）测定评估血管生成活性。1,7-双(4-(3,5,6-三甲基吡嗪-2-基)-3-甲氧基苯基)-1,6-庚二烯-3,5-二酮 (4) 和 3 α,12 α-二羟基- 5β-dholanic acid-3,5,6-trimethylpyrazin-2-methylester (5) 不仅对这些癌细胞显示出抗增殖活性，而且还能显着抑制 CAM 中的正常血管生成。
• Glycyrrhetinic acid-mediated nanoparticles of hepatic targeted drug delivery system, process for preparing the same and use thereof
  申请人：Yuan Zhi

  公开号：US09173852B2

  公开（公告）日：2015-11-03

  Disclosed are a hepatic targeted drug delivery system and a process for preparing the same. Also disclosed is a method for treating liver cancer.

  本发明公开了一种肝靶向药物传递系统及其制备方法。还公开了一种治疗肝癌的方法。
• Constructing Quaternary Carbons from <i>N</i>-(Acyloxy)phthalimide Precursors of Tertiary Radicals Using Visible-Light Photocatalysis
  作者：Gerald Pratsch、Gregory L. Lackner、Larry E. Overman

  DOI：10.1021/acs.joc.5b00795

  日期：2015.6.19

  Tertiary carbon radicals have notable utility for uniting complex carbon fragments with concomitant formation of new quaternary carbons. This article explores the scope, limitations, and certain mechanistic aspects of Okada's method for forming tertiary carbon radicals from N-(acyloxy)phthalimides by visible-light photocatalysis. Optimized conditions for generating tertiary radicals from N-(acyloxy)phthalimide derivatives of tertiary carboxylic acids by visible-light irradiation in the presence of 1 mol % of commercially available Ru(bpy)(3)(PF6)(2), diethyl 1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate (8), and i-Pr2NEt and their coupling in dichloromethane at room temperature with alkene acceptors were developed. Four representative tertiary N-(acyloxy)-phthalimides and 15 alkene radical acceptors were examined. Both reductive couplings with electron-deficient alkenes and radical substitution reactions with allylic and vinylic bromides and chlorides were examined with many such reactions occurring in good yield using only a slight excess (typically 1.5 equiv) of the alkene. In general, the yields of these photocatalytic reactions were higher than the analogous transformations of the corresponding N-phthalimidoyl oxalates. Deuterium labeling and competition experiments reveal that the reductive radical coupling of tertiary N-(acyloxy)phthalimides with electron-deficient alkenes can be terminated by both hydrogen-atom transfer and single-electron reduction followed by protonation, and that this mechanistic duality is controlled by the presence or absence of i-Pr2NEt.