16-formyl-17-(1H-1,2,4-triazole-1-yl)androsta-5,16-diene-3β-yl p-nitrobenzoate | 1470067-82-3

• 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: 16-formyl-17-(1H-1,2,4-triazole-1-yl)androsta-5,16-diene-3β-yl p-nitrobenzoate
• 英文别名: [(3S,8R,9S,10R,13S,14S)-16-formyl-10,13-dimethyl-17-(1,2,4-triazol-1-yl)-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] 4-nitrobenzoate
• CAS: 1470067-82-3
• 化学式: C₂₉H₃₂N₄O₅
• 分子量: 516.597
• InChiKey: KWPBRBRTWYIWJV-UMALJDHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  17-oxaandrost-5-ene-3β-yl p-nitrobenzoate 在 potassium carbonate 、 三氯氧磷 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 16-formyl-17-(1H-1,2,4-triazole-1-yl)androsta-5,16-diene-3β-yl p-nitrobenzoate
  参考文献：
  名称：

  Cytotoxic effect of novel dehydroepiandrosterone derivatives on different cancer cell lines

  摘要：

  The aim of this study was to determine the cytotoxic effect of human cancer cells on three series of novel dehydroepiandrosterone derivatives containing triazole or pyrazole rings at C-17 and an ester moiety at C-3 of the androstane skeleton. The panel cancer cells used in this study were the following: PC-3, MCF-7 and SKLU-1.The results from this study indicated that the steroidal derivatives 4a-4e and 4f-4k showed the highest cytotoxic potency. This difference in this activity could be attributed to the ability of the triazole (three nitrogen atoms) to form stronger hydrogen bonds with the active site of the cell as compared to the pyrazole group having two nitrogen atoms.Compounds 4f-4k having an aromatic ester at C-3 showed an enhanced cytotoxic activity as compared to their aliphatic counterparts 4a-4e. Apparently the electronegative phenyl ring increased the polarity of the molecule, thus increasing the dipole dipole association of the steroidal molecule with the reactive site of the cell. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.031