methyl 3,11-dioxo-4-oxa-A-homo-olean-12-en-30-oate | 1158817-88-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: methyl 3,11-dioxo-4-oxa-A-homo-olean-12-en-30-oate
• 英文别名: methyl 3,4-epoxy-3,11-dioxo-3,4-seco-18β-olean-12-ene-30-carboxylate；4-hydroxy-3,4-seco-11-oxo-18β-olean-12-ene-3,30-dioic acid 3,4-lactone 30-methyl ester；methyl (1R,2S,5S,8S,10R,14R,15S,21R)-1,2,5,8,15,20,20-heptamethyl-13,18-dioxo-19-oxapentacyclo[12.9.0.02,11.05,10.015,21]tricos-11-ene-8-carboxylate
• CAS: 1158817-88-9
• 化学式: C₃₁H₄₆O₅
• 分子量: 498.703
• InChiKey: KUUBZYCSTRNXHW-GJIZTULQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3,11-dioxo-4-oxa-A-homo-olean-12-en-30-oate 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 生成 3,4-seco-11-oxo-18β-olean-4(23),12-dien-3,30-dioic acid 3-isopropyl 30-methyl ester
  参考文献：
  名称：

  DERIVATIVE OF 18beta-GLYCYRRHETINIC ACID APT TO SUPPRESS CANCER CELLS

  摘要：

  本发明涉及与18β-甘草酸衍生物相关，适于抑制癌细胞，所选取自包括结构I和结构II的一组中的一种，其中残基R1选择自CH3和CH2C6H5之一，残基R2选择自COOCH3、COOCH2CH3、COOCH(CH3)2、CONHCH2CH3、CONHCH2CH2CH3和CONHCH2(CH3)2之一，残基R3选择自COOCH2CH3、COOCH(CH3)2、CONHCH2CH3、CONHCH2CH2CH3和CONHCH2(CH3)2之一。

  公开号：

  US20130109752A1
• 作为产物：
  描述：

  (3beta,20beta)-3-羟基-11-氧代-齐墩果-12-烯-29-酸甲酯 在 Jones reagent 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 methyl 3,11-dioxo-4-oxa-A-homo-olean-12-en-30-oate
  参考文献：
  名称：

  新型A环裂解甘草次酸衍生物的合成及其抗增殖活性

  摘要：

  通过A环的打开以及氨基酸的偶联合成了一系列新的甘草次酸衍生物。针对一组九种人类癌细胞系评估了衍生物的抗增殖活性。化合物 17 是最活跃的化合物，对 Jurkat 细胞的 IC50 为 6.1 µM，其效力比甘草次酸强 17 倍，并且对癌细胞系的选择性高出 10 倍。Jurkat 细胞的进一步生物学研究表明，化合物 17 的抗增殖活性是由于细胞周期停滞在 S 期并诱导细胞凋亡。

  DOI：

  10.3390/molecules24162938

文献信息

• Synthesis and Properties of Methyl 3,4-Epoxy-3,11-dioxo-3,4seco-18β-olean-12-ene-30-carboxylate in a New Reaction of Organoaluminium Compounds
  作者：V. A. Vydrina、A. A. Kravchenko、D. A. Sataraev、R. R. Sayakhov、A. G. Tolstikov、G. Yu. Ishmuratov

  DOI：10.1134/s1070428020020116

  日期：2020.2

  AbstractAn effective reagent (performic acid) was proposed for the Bayer–Villiger oxidation of glycyrrhetic acid methyl ester to the corresponding oxepan-2-one. The low-temperature (–70°C) reduction of the latter with excess (5 equiv) diisobutylaluminium hydride in CH2Cl2 resulted in the isolation of 3,4-seco-18β-oleane-4(23),9(11),12-triene-3,30-diol as the main product, while the expected (R)-3,

  摘要有人提出了一种有效的试剂（过甲酸），用于将甘草次酸甲酯的Bayer-Villiger氧化为相应的oxepan-2-one。在CH 2 Cl 2中用过量（5当量）氢化二异丁基铝将后者进行低温（–70°C）还原，从而分离出3,4- seco -18β-oleane-4（23），9（11） ），12-三烯-3,30-二醇为主要产物，而预期的（R）-3,4-环氧-3-异丁氧基-3,4- seco -18β-油烷-11,12-dien-30 -ol是次要产品。
• Synthesis, anti-inflammatory, and antioxidant activities of 18β-glycyrrhetinic acid derivatives as chemical mediators and xanthine oxidase inhibitors
  作者：Dravidum Maitraie、Chi-Feng Hung、Huang-Yao Tu、Ya-Ting Liou、Bai-Luh Wei、Shyh-Chyun Yang、Jih-Pyang Wang、Chun-Nan Lin

  DOI：10.1016/j.bmc.2009.02.025

  日期：2009.4

  Twenty 18 beta-glycyrrhetic acid (18 beta-GA) derivatives 2-21 including 13 new 18 beta-GA derivatives were synthesized and evaluated as anti-inflammatory and antioxidant agents. Compounds 7 and 20 with a 3,4-seco-structure and compound 6 with a lactone moiety showed potent inhibitory effect on superoxide anion generation in rat neutrophils response to fMLP/CB and PMA, respectively. Compound 6 with a lactone moiety revealed stronger inhibitory effect on XO activity than those of compounds 13 and 14 with a 3,4-seco-struture. Compound 14, a 30-isoproylcarbamoyl seco-compound exhibited potent inhibitory effect on NO accumulation and iNOS protein expression while compounds 3, 10, 13, 15, 17, and 21 revealed potent inhibitory effect on tumor necrosis factor-alpha (TNF-alpha) formation in RAW 264.7 cells in response to lipopolysaccharide (LPS). The cleavage of ring A of 3 attenuated the inhibitory effect on TNF-alpha formation in RAW 264.7 cells in response to LPS except for 17. The present results suggested these compounds were potential to be served as anti-inflammatory and antioxidant agents. (c) 2009 Elsevier Ltd. All rights reserved.
• 18β-Glycyrrhetinic acid derivatives induced mitochondrial-mediated apoptosis through reactive oxygen species-mediated p53 activation in NTUB1 cells
  作者：Kai-Wei Lin、A-Mei Huang、Tzyh-Chyuan Hour、Shyh-Chyun Yang、Yeong-Shiau Pu、Chun-Nan Lin

  DOI：10.1016/j.bmc.2011.05.054

  日期：2011.7

  Twenty six 18 beta-glycyrrhetinic acid (GA) (1) derivatives 2-27 including twelve new GA derivatives 10, 11, 13-17, 21-25 were synthesized and evaluated for cytotoxicities against NTUB1 cells (human bladder cancer cell lines). seco-Compounds 9, 25, and 27 are the most potent compounds of this series, inhibiting cell growth of human NTUB1 cells with an IC50 values of 2.34 +/- 0.28, 4.76 +/- 1.15, and 3.31 +/- 0.61 mu M, respectively. Exposure of NTUB1 to 25 for 24 h significantly increased the production of reactive oxygen species (ROS). Flow cytometric analysis exhibited that treatment of NTUB1 with 25 did not induce cell cycle arrest but accompanied by an increase of apoptotic cell death in a dose-dependant manner after 24 h. Mitochondrial membrane potential (MMP) decreased significantly in a dose-dependant manner when the NTUB1 cells were exposed to 25 for 24 h. Marked collapse of the MMP suggested that dysfunction of the mitochondria may be involved in the oxidative burst and apoptosis induced by 25. Western blot analysis shows that NTUB1 cells treated with 25 increased the level of p-p53 in a dose-dependant manner. Further, NAC treatment prevented p53 phosphorylation stimulated by 25. These results suggested that 25 induced a mitochondrial-mediated apoptosis in NTUB1 cells through activation of p53, which are mainly mediated ROS generated by 25. (C) 2011 Elsevier Ltd. All rights reserved.