3,4-seco-11-oxo-18β-olean-4(23),12-diene-3,30-dioic acid 3-isopropyl ester | 1158817-89-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3,4-seco-11-oxo-18β-olean-4(23),12-diene-3,30-dioic acid 3-isopropyl ester
• CAS: 1158817-89-0
• 化学式: C₃₃H₅₀O₅
• 分子量: 526.757
• InChiKey: FRCJBGBFBKPROD-RJOWQFIDSA-N

物化性质

• 熔点：
  94-99 °C
• 沸点：
  607.0±55.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.54
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  80.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3,11-dioxo-4-oxa-A-homo-olean-12-en-30-oic acid 、 异丙醇 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到3,4-seco-11-oxo-18β-olean-4(23),12-diene-3,30-dioic acid 3-isopropyl ester
  参考文献：
  名称：

  Synthesis, anti-inflammatory, and antioxidant activities of 18β-glycyrrhetinic acid derivatives as chemical mediators and xanthine oxidase inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2009.02.025