methyl (3β)-3-(([(2L)-(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)thio]acetyl)oxy)-11-oxoolean-12-en-30-oate | 1345513-24-7

• 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: methyl (3β)-3-(([(2L)-(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)thio]acetyl)oxy)-11-oxoolean-12-en-30-oate
• 英文别名: methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-2,4a,6a,6b,9,9,12a-heptamethyl-10-[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[(2-methylpropan-2-yl)oxycarbonylsulfanyl]propanoyl]oxy-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate
• CAS: 1345513-24-7
• 化学式: C₄₄H₆₉NO₉S
• 分子量: 788.099
• InChiKey: VJKFHBMLHFHTQA-KKDQEPGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  55
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  160
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl (3β)-3-(([(2L)-(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)thio]acetyl)oxy)-11-oxoolean-12-en-30-oate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以43%的产率得到dimethyl (3β,3'β)-3,3'-(dithiobis([(2S)-2-amino-1-oxoethane-2,1-diyl]oxy)) bis(11-oxoolean-12-en-30-oate)
  参考文献：
  名称：

  Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives

  摘要：

  Triterpenoic acids show many pharmacological effects, among them an antiinflammatory or an antitumor activity. One of these, glycyrrhetinic acid (1) is of interest because of its antitumor profile. Glycyrrhetinic acid is not only cytotoxic but also triggers apoptosis in various human tumor cell lines. To improve the cytotoxicity of parent 1 we set out to synthesize new derivatives of it-differing in structure and lipophilicity. These compounds were tested in a sulforhodamine B assay for cytotoxicity, and screened for their ability to induce apoptosis using an acridine orange/ethidium bromide assay and trypan blue staining. The most active compound, 34, a benzyl glycyrrhetinate holding an extra 3-N-(3-aminopropyl)glycyl substituent showed IC50 between 1.96 and 5.14 mu m for five human cancer cell lines and triggers apoptosis in 80% of the cells. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.038
• 作为产物：
  描述：

  甘草次酸 在 4-二甲氨基吡啶 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 methyl (3β)-3-(([(2L)-(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)thio]acetyl)oxy)-11-oxoolean-12-en-30-oate
  参考文献：
  名称：

  Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives

  摘要：

  Triterpenoic acids show many pharmacological effects, among them an antiinflammatory or an antitumor activity. One of these, glycyrrhetinic acid (1) is of interest because of its antitumor profile. Glycyrrhetinic acid is not only cytotoxic but also triggers apoptosis in various human tumor cell lines. To improve the cytotoxicity of parent 1 we set out to synthesize new derivatives of it-differing in structure and lipophilicity. These compounds were tested in a sulforhodamine B assay for cytotoxicity, and screened for their ability to induce apoptosis using an acridine orange/ethidium bromide assay and trypan blue staining. The most active compound, 34, a benzyl glycyrrhetinate holding an extra 3-N-(3-aminopropyl)glycyl substituent showed IC50 between 1.96 and 5.14 mu m for five human cancer cell lines and triggers apoptosis in 80% of the cells. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.038