4,16-pregnadien-6,20-dione-3β-yl-1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 4,16-pregnadien-6,20-dione-3β-yl-1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate
• 英文别名: [(3S,8R,9S,10R,13S,14S)-17-acetyl-10,13-dimethyl-6-oxo-1,2,3,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-yl] 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetate
• 化学式: C₄₀H₄₂ClNO₆
• 分子量: 668.23
• InChiKey: COVMQMACUFTWSA-GFCRYOTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  48
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  91.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  16-脱氢孕烯醇酮乙酸酯 在 吡啶 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 氯化亚砜 、 间氯过氧苯甲酸 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 、 丙酮 为溶剂， 反应 7.0h， 生成 4,16-pregnadien-6,20-dione-3β-yl-1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate
  参考文献：
  名称：

  Effect of new hybrids based on 5,16-pregnadiene scaffold linked to an anti-inflammatory drug on the growth of a human astrocytoma cell line (U373)

  摘要：

  In spite of the fact that anaplastic astrocytoma is an uncommon disease, very often the pathology of this disease is associated with lethal effects due to the late diagnosis and unspecific treatments. This paper reports the synthesis and the biological effect on the growth of U373 cell line (human anaplastic astrocytoma) of new hybrid compounds based on 5,16-pregnadiene scaffold linked to an anti-inflammatory drug (6a-e). Moreover, we also determined the cell growth effect of five non-steroidal anti-inflammatory drugs (naproxen, ibuprofen, ketoprofen, indomethacin and sulindac) as well as the free steroidal alcohol 5. The results from this study indicated that sulindac as well as compound 5 decreased the number of U373 cells at different concentrations. However, when an anti-inflammatory drug was bound to the steroidal structure (5), the resulting compounds (6a-e) showed an enhanced biological effect with exception of hybrid 6c. Furthermore, derivative 6e (sulindac hybrid) did not allow cell growth during six days of experiment at a concentration of 10 mu M. The overall data indicated that these molecules showed an anti-proliferative activity on anaplastic astrocytoma cell line. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.048