4β,5β-epoxy-17-methyl-3,17-dioxo-16,17-secoandrostane-16-nitrile | 1040236-06-3

• 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: 4β,5β-epoxy-17-methyl-3,17-dioxo-16,17-secoandrostane-16-nitrile
• CAS: 1040236-06-3
• 化学式: C₂₀H₂₇NO₃
• 分子量: 329.439
• InChiKey: ZYRKXRPKOIXBCQ-XQIDNCIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  70.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  17-methyl-16-nitrile-16,17-seco-4-androstene-3,17-dione 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 4α,5α-epoxy-17-methyl-3,17-dioxo-16,17-secoandrostane-16-nitrile 、 4β,5β-epoxy-17-methyl-3,17-dioxo-16,17-secoandrostane-16-nitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of a series of A,B-ring modified 16,17-secoandrostane derivatives

  摘要：

  The starting compound for the synthesis of 16,17-secoandrostane derivatives with the 4-en-3-on, 1,4-dien-3-on, 4,6-dien-3-on, and 1,4,6-trien-3-on systems was 3 beta-hydroxy-17-methyl-16,17-secoandrost-5-en-16-nitrile-17-one (1), the Oppenauer oxidation of which yielded the corresponding 4-en-3-one derivative 2. Dehydrogenation of compound 2 with the aid of 2,3,5,6-tetrachloro-1,4-benzoquinone (chloranil) gave the three products: 17-methyl-16,17-secoandrosta-1,4-dien-3,17-dione-16-nitrile (3), 17-methyl-16,17-secoandrosta-4,6-dien-3,17-dione-16-nitrile (4), and 17-methyl-16,17-secoandrosta-1,4,6-trien-3,17-dione-16-nitrile (5). On the other hand, epoxidation of compound 2 resulted in a mixture of alpha and beta isomers of 4,5-epoxy-17-methyl-16,17-secoandrosta-3,17-dione-16-nitrile (6 and 7). Opening of the oxirane rings of the mixture of 6 and 7 by the action of formic acid yielded the 4-hydroxy-4-en derivative 8. Antiaromatase activity and in vitro cytotoxicity against three tumor cell lines (human breast adenocarcinoma ER+, MCF-7, human breast adenocarcinoma ER-, MDA-MB-231, and prostate cancer PC3) of selected compounds were evaluated. Compound 2 exhibited a relatively strong inhibition of aromatase and extremely potent cytotoxicity against PC3 cells. Compound 8 showed satisfactory cytotoxicity against MCF-7 cells. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2008.01.002