28-N-methyl hexanoate oleanate 3-O-α-D-mannopyranoside | 1443136-36-4

• 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-α-D-mannopyranoside
• 英文别名: methyl 6-[[(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carbonyl]amino]hexanoate
• CAS: 1443136-36-4
• 化学式: C₄₃H₇₁NO₉
• 分子量: 746.038
• InChiKey: ZLMJVGLHRCNPHL-MSBREJBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  53
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  28-N-methyl hexanoate oleanate 3-O-α-D-mannopyranoside 在 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 四丁基溴化铵 、 碳酸氢钠 、 sodium bromide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 叔丁醇 为溶剂， 反应 3.0h， 生成 hexanoate oleanate 3-O-α-D-mannocuronopyranoside
  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：

  [(2R,3R,4S,5S,6S)-3,4,5-三苯甲酰氧基-6-(2,2,2-三氯亚氨代乙酰)氧基-四氢吡喃-2-基]甲基苯甲酸酯 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 28-N-methyl hexanoate oleanate 3-O-α-D-mannopyranoside
  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

• 齐墩果酸甘露糖苷化合物及其在制备治疗抗糖尿病药物中的应用
  申请人：西北大学

  公开号：CN117720610A

  公开（公告）日：2024-03-19

  本发明公开了一类齐墩果酸甘露糖苷化合物及其在制备治疗抗糖尿病药物中的应用，该化合物的结构式为#imgabs0#式中R代表脂肪酯基或杂原子取代基，R′代表氢原子或乙酰基，其是以齐墩果酸C28‑氨基正己酸甲酯为起始原料，在其3位羟基引入D‑甘露糖基，而后将D‑甘露糖基的C6‑OH转化为脂肪酯基或杂原子取代基、其它位羟基裸露或转化为乙酰基而成。药理活性测试显示该类化合物对蛋白质酪氨酸磷酸酯酶1B具有很好的抑制活性，说明此类齐墩果酸甘露糖苷化合物可以作为一种新型的抗糖尿病药物而加以研究利用。
• 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.