28-N-methyl hexanoate oleanate 3-O-β-D-glucuronopyranoside | 533934-73-5

• 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: 28-N-methyl hexanoate oleanate 3-O-β-D-glucuronopyranoside
• 英文别名: (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-[(6-methoxy-6-oxohexyl)carbamoyl]-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 533934-73-5
• 化学式: C₄₃H₆₉NO₁₀
• 分子量: 760.022
• InChiKey: BPFYPRSUPVAPCR-DHNQIJCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  54
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  28-N-methyl hexanoate oleanate 3-O-β-D-glucuronopyranoside 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以91%的产率得到hexanoate oleanate 3-O-β-D-glucuronopyranoside
  参考文献：
  名称：

  Synthesis and biological evaluation of oleanolic acid derivatives as PTP1B inhibitors

  摘要：

  Twenty-four sugar-substituted oleanolic acid derivatives (1a-1f, 2a-2j, and 3a-3h) were synthesized in a concise and efficient strategy and their effects on the inhibition of protein tyrosine phosphatase 1B (PTP1B) and insulin-sensitizing response were evaluated in vitro. Several derivatives showed moderate to good inhibitory activities against PTP1B, and especially compounds 2f, 2h, 3d and 3e exhibited the most potent inhibitory activities with the IC50 values of 1.91, 12.2, 9.21 and 0.56 mu M against PTP1B, respectively. Furthermore, compounds 2g-2h and 3b-3e displayed good insulin-sensitizing activities with the response values ranging from 21.52% to 59.58%. Structure-activity relationship study of these sugar-substituted oleanolic acid derivatives demonstrated that PTP1B inhibitory activity and insulin-sensitizing response were strongly influenced by both the carbohydrate moiety at the C-3 position and the long acidic chain at C-28 position of oleanolic acid. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.001
• 作为产物：
  描述：

  methyl 6-[[(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carbonyl]amino]hexanoate 在 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 四丁基溴化铵 、 sodium methylate 、 碳酸氢钠 、 sodium bromide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 7.5h， 生成 28-N-methyl hexanoate oleanate 3-O-β-D-glucuronopyranoside
  参考文献：
  名称：

  Synthesis and biological evaluation of oleanolic acid derivatives as PTP1B inhibitors

  摘要：

  Twenty-four sugar-substituted oleanolic acid derivatives (1a-1f, 2a-2j, and 3a-3h) were synthesized in a concise and efficient strategy and their effects on the inhibition of protein tyrosine phosphatase 1B (PTP1B) and insulin-sensitizing response were evaluated in vitro. Several derivatives showed moderate to good inhibitory activities against PTP1B, and especially compounds 2f, 2h, 3d and 3e exhibited the most potent inhibitory activities with the IC50 values of 1.91, 12.2, 9.21 and 0.56 mu M against PTP1B, respectively. Furthermore, compounds 2g-2h and 3b-3e displayed good insulin-sensitizing activities with the response values ranging from 21.52% to 59.58%. Structure-activity relationship study of these sugar-substituted oleanolic acid derivatives demonstrated that PTP1B inhibitory activity and insulin-sensitizing response were strongly influenced by both the carbohydrate moiety at the C-3 position and the long acidic chain at C-28 position of oleanolic acid. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.001

文献信息

• Synthesis and biological evaluation of oleanolic acid derivatives as PTP1B inhibitors
  作者：Qing-Chao Liu、Tian-Tian Guo、Lei Zhang、Yue Yu、Peng Wang、Ju-Fang Yang、Ying-Xia Li

  DOI：10.1016/j.ejmech.2013.03.001

  日期：2013.5

  Twenty-four sugar-substituted oleanolic acid derivatives (1a-1f, 2a-2j, and 3a-3h) were synthesized in a concise and efficient strategy and their effects on the inhibition of protein tyrosine phosphatase 1B (PTP1B) and insulin-sensitizing response were evaluated in vitro. Several derivatives showed moderate to good inhibitory activities against PTP1B, and especially compounds 2f, 2h, 3d and 3e exhibited the most potent inhibitory activities with the IC50 values of 1.91, 12.2, 9.21 and 0.56 mu M against PTP1B, respectively. Furthermore, compounds 2g-2h and 3b-3e displayed good insulin-sensitizing activities with the response values ranging from 21.52% to 59.58%. Structure-activity relationship study of these sugar-substituted oleanolic acid derivatives demonstrated that PTP1B inhibitory activity and insulin-sensitizing response were strongly influenced by both the carbohydrate moiety at the C-3 position and the long acidic chain at C-28 position of oleanolic acid. (C) 2013 Elsevier Masson SAS. All rights reserved.