3β-{2-[2-(2-{4-[4-(5-{(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl}pentanamido)benzoyl]benzamido}ethoxy)ethoxy]acetoxy}olean-12-en-28-oic acid | 1356007-45-8

• 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: 3β-{2-[2-(2-{4-[4-(5-{(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl}pentanamido)benzoyl]benzamido}ethoxy)ethoxy]acetoxy}olean-12-en-28-oic acid
• 英文别名: (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[2-[2-[2-[[4-[4-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]benzoyl]benzoyl]amino]ethoxy]ethoxy]acetyl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 1356007-45-8
• 化学式: C₆₀H₈₂N₄O₁₀S
• 分子量: 1051.4
• InChiKey: QPZGQBBGKVWOLN-BNSDNVOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  75
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  224
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  4(4-nitrobenzoyl)benzoic acid chloride 在 吡啶 、 tin(II) chloride dihdyrate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 3β-{2-[2-(2-{4-[4-(5-{(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl}pentanamido)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

文献信息

• Design and synthesis of novel photoaffinity probes for study of the target proteins of oleanolic acid
  作者：Liying Zhang、Yingxia Zhang、Jizhe Dong、Jun Liu、Luyong Zhang、Hongbin Sun

  DOI：10.1016/j.bmcl.2011.11.123

  日期：2012.1

  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.