3β-[2-(2-{2-[4-(4-{2-[4-({5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyloxy}methyl)-1H-1,2,3-triazol-1-yl]acetamido}benzoyl)benzamido]ethoxy}ethoxy)acetoxy]olean-12-en-28-oic acid | 1356007-74-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: 3β-[2-(2-{2-[4-(4-{2-[4-({5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyloxy}methyl)-1H-1,2,3-triazol-1-yl]acetamido}benzoyl)benzamido]ethoxy}ethoxy)acetoxy]olean-12-en-28-oic acid
• CAS: 1356007-74-3
• 化学式: C₆₅H₈₇N₇O₁₂S
• 分子量: 1190.51
• InChiKey: YJWMDJHAZUDNHN-AEYRPUHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.48
• 重原子数：
  85.0
• 可旋转键数：
  23.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  255.47
• 氢给体数：
  5.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  4(4-nitrobenzoyl)benzoic acid chloride 在 吡啶 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 tin(II) chloride dihdyrate 、 sodium ascorbate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 3β-[2-(2-{2-[4-(4-{2-[4-({5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyloxy}methyl)-1H-1,2,3-triazol-1-yl]acetamido}benzoyl)benzamido]ethoxy}ethoxy)acetoxy]olean-12-en-28-oic acid
  参考文献：
  名称：

  Design and synthesis of novel photoaffinity probes for study of the target proteins of oleanolic acid

  摘要：

  To explore the molecular mechanisms of oleanolic acid, two novel photoaffinity probes were synthesized based on the structure-activity relationship reported previously. Their potency were evaluated in an enzyme inhibition assay against rabbit muscle glycogen phosphorylase a (RMGPa), a known target protein of oleanolic acid. The inhibitory activity of probe 2 was only about two-fold less potent than the mother compound oleanolic acid. The photoaffinity labeling experiments were also performed and two proteins were specifically tagged by probe 2. The results suggest that the synthesized probes could be used as powerful tools to isolate and identify the target proteins of oleanolic acid. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.123