(3β,18β)-methyl 3-amino-11-oxoolean-12-en-30-oate | 39775-94-5

• 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: (3β,18β)-methyl 3-amino-11-oxoolean-12-en-30-oate
• 英文别名: (3β,18β,20β)-3-amino-11-oxoolean-12-en-29-oic acid methyl ester；methyl (3β)-3-amino-11-oxo-olean-12-en-30-oate；methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-amino-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: 39775-94-5
• 化学式: C₃₁H₄₉NO₃
• 分子量: 483.735
• InChiKey: YCCMXTKMPWETBU-BDANYOJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3β,18β)-methyl 3-amino-11-oxoolean-12-en-30-oate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 methyl (3β)-3-(L-alanylamino)-11-oxo-olean-12-en-30-oate
  参考文献：
  名称：

  Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives

  摘要：

  Triterpenoic acids show many pharmacological effects, among them an antiinflammatory or an antitumor activity. One of these, glycyrrhetinic acid (1) is of interest because of its antitumor profile. Glycyrrhetinic acid is not only cytotoxic but also triggers apoptosis in various human tumor cell lines. To improve the cytotoxicity of parent 1 we set out to synthesize new derivatives of it-differing in structure and lipophilicity. These compounds were tested in a sulforhodamine B assay for cytotoxicity, and screened for their ability to induce apoptosis using an acridine orange/ethidium bromide assay and trypan blue staining. The most active compound, 34, a benzyl glycyrrhetinate holding an extra 3-N-(3-aminopropyl)glycyl substituent showed IC50 between 1.96 and 5.14 mu m for five human cancer cell lines and triggers apoptosis in 80% of the cells. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.038
• 作为产物：
  描述：

  3,11-Dioxo-Δ¹²-oleanen-30-saeuremethylester-3-oxim 在 盐酸 、 titanium(III) chloride 、 硼烷-叔丁基胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 以87.5%的产率得到(3β,18β)-methyl 3-amino-11-oxoolean-12-en-30-oate
  参考文献：
  名称：

  Synthesis of glycyrrhetinic acid derivatives for the treatment of metabolic diseases

  摘要：

  The effect of glycyrrhetinic acid (GA) and GA-derivatives towards 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD) was investigated. Novel compounds with modi. cations at positions C-3, C-11 and C-29 of the GA skeleton were prepared. Single crystal X-ray diffraction data of selected substances are reported and discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.036

文献信息

• First Occurrence of a Furano-glycyrrhetinoate and Its Cytotoxicity
  作者：Lucie Heller、Sven Sommerwerk、Felix Tzschöckell、Jana Wiemann、Stefan Schwarz、Bianka Siewert、Ahmed Al-Harrasi、René Csuk

  DOI：10.1002/ardp.201500318

  日期：2015.12

  (18β)‐glycyrrhetinic acid (1), and the cytotoxicity of some derivatives was investigated by photometric SRB assays employing several human tumor cell lines. In summary, (18β)‐1 is slightly more cytotoxic than its (18α) epimer 4, but its cytotoxicity is negligible. Higher cytotoxicity was observed for the esters 2 and 5 and for the 3‐O‐acetylated esters 3 and 6. Cytotoxicity was improved dramatically when the

  (18α)-甘草次酸 (4) 由 (18β)-甘草次酸 (1) 制备，并通过使用几种人类肿瘤细胞系的光度 SRB 测定研究了一些衍生物的细胞毒性。总之，(18β)-1 的细胞毒性略高于其 (18α) 差向异构体 4，但其细胞毒性可以忽略不计。对酯 2 和 5 以及 3-O-乙酰化酯 3 和 6 观察到更高的细胞毒性。当 C-3 位的羟基被氨基部分取代时，细胞毒性显着提高。SeO2 氧化提供了一种新型呋喃甘草次酸 15。有趣的是，它的硒类似物 16 对所测试的肿瘤细胞系的细胞毒性大约低 5 到 6 倍，并且在用硒替代氧气时失去了肿瘤/非肿瘤选择性取代基。
• Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives
  作者：René Csuk、Stefan Schwarz、Bianka Siewert、Ralph Kluge、Dieter Ströhl

  DOI：10.1016/j.ejmech.2011.08.038

  日期：2011.11

  Triterpenoic acids show many pharmacological effects, among them an antiinflammatory or an antitumor activity. One of these, glycyrrhetinic acid (1) is of interest because of its antitumor profile. Glycyrrhetinic acid is not only cytotoxic but also triggers apoptosis in various human tumor cell lines. To improve the cytotoxicity of parent 1 we set out to synthesize new derivatives of it-differing in structure and lipophilicity. These compounds were tested in a sulforhodamine B assay for cytotoxicity, and screened for their ability to induce apoptosis using an acridine orange/ethidium bromide assay and trypan blue staining. The most active compound, 34, a benzyl glycyrrhetinate holding an extra 3-N-(3-aminopropyl)glycyl substituent showed IC50 between 1.96 and 5.14 mu m for five human cancer cell lines and triggers apoptosis in 80% of the cells. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis of glycyrrhetinic acid derivatives for the treatment of metabolic diseases
  作者：Igor Beseda、Laszlo Czollner、Priti S. Shah、Rupesh Khunt、Rawindra Gaware、Paul Kosma、Christian Stanetty、Maria Carmen del Ruiz-Ruiz、Hassan Amer、Kurt Mereiter、Thierry Da Cunha、Alex Odermatt、Dirk Claßen-Houben、Ulrich Jordis

  DOI：10.1016/j.bmc.2009.10.036

  日期：2010.1

  The effect of glycyrrhetinic acid (GA) and GA-derivatives towards 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD) was investigated. Novel compounds with modi. cations at positions C-3, C-11 and C-29 of the GA skeleton were prepared. Single crystal X-ray diffraction data of selected substances are reported and discussed. (C) 2009 Elsevier Ltd. All rights reserved.