benzyl 3β-acetylglycyrrhetate | 127290-98-6

• 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: benzyl 3β-acetylglycyrrhetate
• 英文别名: benzyl O-acetylglycyrrhetate；benzyl 3β-acetyloxy-11-oxo-olean-12-en-30-oate；benzyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-acetyloxy-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-carboxylate
• CAS: 127290-98-6
• 化学式: C₃₉H₅₄O₅
• 分子量: 602.855
• InChiKey: NCVFCFQIYJLJOY-HMPDDEAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  44
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甘草次酸 在 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.5h， 生成 benzyl 3β-acetylglycyrrhetate
  参考文献：
  名称：

  具有细胞毒性特性的齐墩果酸和甘草次酸衍生物的设计和制备

  摘要：

  Background: The structural modification of natural products with the aim to improve the anticancer activity is a popular current research direction. The pentacyclic triterpenoid compounds oleanolic acid (OA) and glycyrrhetinic acid (GA) are distributed widely in nature.Methods: In this study, various oleanolic acids and glycyrrhetinic acids were designed and synthesized by using the combination principle. The in vitro anticancer activities of new OA and GA derivatives were tested by the 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) method with SGC-7901 (gastric cancer), MCF-7 (breast cancer), Eca-109 (esophageal cancer), HeLa (cervical cancer), Hep-G2 (hepatoma cancer) and HSF (normal human skin fibroblast) cells.Results and conclusion: The screening results showed that the compound 3m presented the highest inhibitory activities against SGC-7901, MCF-7 and Eca-109 cell lines with IC50 values of 7.57 +/- 0.64 mu M, 5.51 +/- 0.41 mu M and 5.03 +/- 0.56 mu M, respectively. In addition, this compound also showed effective inhibition of Hep-G2 cells with an IC50 value of 4.11 +/- 0.73 mu M. Moreover, compound 5b showed the strongest inhibitory activity against Hep-G2 cells with an IC50 value of 3.74 +/- 0.18 mu M and compound 3l showed strong selective inhibition of the HeLa cells with the lowest IC50 value of 4.32 +/- 0.89 mu M. A series of pharmacology experiments indicated that compound 5b could induce Hep-G2 cells autophagy and apoptosis. These compounds will expand the structural diversity of anti-cancer targets and confirm the prospects for further research.

  DOI：

  10.2147/dddt.s166051

文献信息

• Studies on the enzyme immunoassay of bio-active constituents contained in oriental medicinal drugs. V. Preparation of bovine serum albumin conjugate and .BETA.-galactosidase labelled antigen for enzyme immunoassay of 3.BETA.-(monoglucuron-1'.BETA.-yl)-18.BETA.-glycyrrhetic acid.
  作者：Matao KANAOKA、Hiromi KATO、Saburo YANO

  DOI：10.1248/cpb.38.221

  日期：——

  In order to prepare an immunogen for enzyme immunoassay of 3β-(monoglucuron-1'-β-yl)-18β-glycyrrhetic acid (3MGA), which was isolated from a patient with glycyrrhizin-induced pseudoaldosteronisms, benzyl glycyrrhetate (3) was allowed to react with an acetobromosugar (2) in the presence of silver carbonate to give benzyl 3β-(methyl2', 3', 4'-triacetyl-glucuron-1'β-yl)-glycyrrhetate (5) and methyl 3', 4'-diacetyl-α-1', 2'-O-[1-(benzyl glycyrrhet-3β-yl)-ethylidene]-D-glucuronate (4). On the other hadn, this reaction was carried out in the presence of mercuric cyanide in nitromethane to give compound 5, benzyl 3β-acetryl glycyrrhetate (6) and benzyl 11-oxo-A-neooleana-3(5), 12-dien-3-oate (7). 4-Aminomethylcyclohexanecarboxylic acid and glycine were introduced as chemical bridges at C-30 of 3β-(tertbutylglucuron-1'β-yl)-glycyrrhetic acid (11) derived from compound 5. The former bridge was used to prepare an immunogenic conjugate with bovine serum albumin, and the latter bridge was used for antigen labelled with β-galactosidase.

  为了制备酶联免疫测定 3β-(单葡糖醛酸-1'-β-基)-18β-甘草亭酸（3MGA）的免疫原，该免疫原是从一名甘草苷诱发的假醛固酮症患者体内分离出来的、在碳酸银存在下，甘草酸苄酯（3）与乙酰溴糖（2）发生反应，生成 3β-（甲基 2'，3'、4'-三乙酰基-葡萄糖醛酸-1'β-基）-甘草酸苄酯 (5) 和 3'，4'-二乙酰基-α-1'，2'-O-[1-(甘草酸苄酯-3β-基)-亚乙基]-D-葡萄糖醛酸甲酯 (4)。另一方面，在硝基甲烷中存在氰化汞的情况下进行该反应，得到化合物 5、3β-乙酰甘草酸苄酯 (6) 和 11-氧代-A-neooleana-3(5), 12-二烯-3-油酸苄酯 (7)。4-Aminomethylcyclohexanecarboxylic acid（4-氨基甲基环己烷羧酸）和甘氨酸被引入到由化合物 5 衍生的 3β-(叔丁基葡萄糖醛酸-1'β-基)-甘草亭酸（11）的 C-30 处作为化学桥。前一个桥用于制备与牛血清白蛋白的免疫原轭合物，后一个桥用于制备与 β-半乳糖苷酶标记的抗原。