3-oxo-7αH,6,11βH-13-acetyl-eudesma-1,4-dien-6,12-olide | 1261992-84-0

• 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: 3-oxo-7αH,6,11βH-13-acetyl-eudesma-1,4-dien-6,12-olide
• 英文别名: (3S,3aS,5aS,9bS)-5a,9-dimethyl-3-(2-oxopropyl)-3a,4,5,9b-tetrahydro-3H-benzo[g][1]benzofuran-2,8-dione
• CAS: 1261992-84-0
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: DARMNVOPJVCVNT-HJXMPXNTSA-N

物化性质

• 熔点：
  165.3-166.2 °C
• 沸点：
  488.6±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙醛 、 (3aS,5aS,9bS)-5a,9-dimethyl-3-methylene-3a,5,5a,9b-tetrahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione 反应 22.0h， 以45%的产率得到3-oxo-7αH,6,11βH-13-acetyl-eudesma-1,4-dien-6,12-olide
  参考文献：
  名称：

  Synthesis of novel α-santonin derivatives as potential cytotoxic agents

  摘要：

  Ten novel alpha-santonin derivatives have been synthesized as cytotoxic agents. The in vitro antitumor activity of these compounds has been evaluated against cancer cells lines. Structure-activity relationships indicate that alpha-methylene-gamma-lactone and endoperoxide functionalities play important roles in conferring cytotoxicity. The compounds 2-4, possessing the alpha-methylene-gamma-lactone group showed IC50 values between 5.70 and 16.40 mu M. Mixture of isomers 5 and 6, with the alpha-methylene-gamma-lactone and endoperoxide functionalities, displayed the greatest activity, with IC50 values between 1.45 and 4.35 mu M. The biological assays conducted with normal cells revealed that the compounds 2, 5 and 6 are selective against cancer cells lines tested. Bioactive lactones described herein and in our previous report did not cause disruption of the cell membrane in mouse erythrocytes. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.10.003

文献信息

• Synthesis of novel α-santonin derivatives as potential cytotoxic agents
  作者：Francisco F.P. Arantes、Luiz C.A. Barbosa、Célia R.A. Maltha、Antônio J. Demuner、Patricia Marçal da Costa、José R.O. Ferreira、Letícia V. Costa-Lotufo、Manoel O. Moraes、Cláudia Pessoa

  DOI：10.1016/j.ejmech.2010.10.003

  日期：2010.12

  Ten novel alpha-santonin derivatives have been synthesized as cytotoxic agents. The in vitro antitumor activity of these compounds has been evaluated against cancer cells lines. Structure-activity relationships indicate that alpha-methylene-gamma-lactone and endoperoxide functionalities play important roles in conferring cytotoxicity. The compounds 2-4, possessing the alpha-methylene-gamma-lactone group showed IC50 values between 5.70 and 16.40 mu M. Mixture of isomers 5 and 6, with the alpha-methylene-gamma-lactone and endoperoxide functionalities, displayed the greatest activity, with IC50 values between 1.45 and 4.35 mu M. The biological assays conducted with normal cells revealed that the compounds 2, 5 and 6 are selective against cancer cells lines tested. Bioactive lactones described herein and in our previous report did not cause disruption of the cell membrane in mouse erythrocytes. (C) 2010 Elsevier Masson SAS. All rights reserved.