17-oxaandrost-5-ene-3β-yl p-nitrobenzoate

• 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: 17-oxaandrost-5-ene-3β-yl p-nitrobenzoate
• 英文别名: 3β-<4-Nitrobenzoyloxy>-Δ⁵-androstenon-(17)；17-oxo-5-androsten-3β-yl 4-nitrobenzoate；17-Oxo-5-androsten-3beta-yl 4-nitrobenzoate；[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] 4-nitrobenzoate
• 化学式: C₂₆H₃₁NO₅
• 分子量: 437.536
• InChiKey: JLLVOVYPSPTUCF-BNCSLUSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  醋酸去氢表雄酮 在 吡啶 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 17-oxaandrost-5-ene-3β-yl p-nitrobenzoate
  参考文献：
  名称：

  Synthesis, antiproliferative activity, acute toxicity and assessment of the antiandrogenic activities of new androstane derivatives

  摘要：

  以市售的(25R)-5-螺烯-3β-醇（薯蓣皂苷）（4）为起始原料，合成了一些 17-氧代-5-雄烯-3β-基酯（9a-9f）和 3β-烷氧基-5-雄烯-17-酮（11a-11e）。评估了合成化合物对前列腺癌细胞株 DU-145 的抗增殖活性、急性毒性和对血清雄激素水平的影响，并与作为阳性对照的非那雄胺进行了比较。其中一些化合物的细胞毒性和抗雄激素活性优于阳性对照。报告了合成化合物的详细合成、光谱数据和生物活性。

  DOI：

  10.1007/s12272-011-0702-2

文献信息

• Cytotoxic effect of novel dehydroepiandrosterone derivatives on different cancer cell lines
  作者：Mariana Garrido、Marisa Cabeza、Francisco Cortés、José Gutiérrez、Eugene Bratoeff

  DOI：10.1016/j.ejmech.2013.02.031

  日期：2013.10

  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.
• Synthesis, antiproliferative activity, acute toxicity and assessment of the antiandrogenic activities of new androstane derivatives
  作者：Neelima Dhingra、T. R. Bhardwaj、Neeraj Mehta、Tapas Mukhopadhyay、Ashok Kumar、Manoj Kumar

  DOI：10.1007/s12272-011-0702-2

  日期：2011.7

  A number of 17-oxo-5-androsten-3β-yl esters (9a–9f) and 3β-alkoxy-5-androsten-17-ones (11a–11e) were synthesized from commercially available (25R)-5-spirosten-3β-ol (Diosgenin) (4) as starting material. The synthesized compounds were evaluated for their antiproliferative activity against the prostate-specific cancer cell line DU-145, acute toxicity and effect on serum androgen levels, and compared with finasteride as positive control. Some of the compounds exhibited better cytotoxicity and antiandrogenic activity than the reference control. The detailed synthesis, spectroscopic data and biological activity of the synthesized compounds are reported.

  以市售的(25R)-5-螺烯-3β-醇（薯蓣皂苷）（4）为起始原料，合成了一些 17-氧代-5-雄烯-3β-基酯（9a-9f）和 3β-烷氧基-5-雄烯-17-酮（11a-11e）。评估了合成化合物对前列腺癌细胞株 DU-145 的抗增殖活性、急性毒性和对血清雄激素水平的影响，并与作为阳性对照的非那雄胺进行了比较。其中一些化合物的细胞毒性和抗雄激素活性优于阳性对照。报告了合成化合物的详细合成、光谱数据和生物活性。