3β-acetoxy-4-nitro-17-oxa-D-homoandrost-4-ene-16-one | 1204831-99-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3β-acetoxy-4-nitro-17-oxa-D-homoandrost-4-ene-16-one
• 英文别名: [(4aS,4bR,8S,10aR,10bS,12aS)-10a,12a-dimethyl-7-nitro-3-oxo-1,4,4a,4b,5,6,8,9,10,10b,11,12-dodecahydronaphtho[2,1-f]isochromen-8-yl] acetate
• CAS: 1204831-99-1
• 化学式: C₂₁H₂₉NO₆
• 分子量: 391.464
• InChiKey: MRISQFQARKJOIW-YQKFBTDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  17-oxa-D-homoandrost-5-en-16-one-3β-yl acetate 在 硝酸 、 sodium nitrite 作用下， 以 乙醚 为溶剂， 反应 0.25h， 以36%的产率得到3β-acetoxy-6-nitro-17-oxa-D-homoandrost-5-ene-16-one
  参考文献：
  名称：

  Synthesis and antitumor activity of new d-seco and d-homo androstane derivatives

  摘要：

  Starting from 30-hydroxy-17-oxo-16,17-secoandrost-5-ene-16-nitrile (1), the new 16,17-secoandrostane derivatives 4-9 were synthesized. On the other hand, 3 beta-hydroxy-17-oxa-D-homoandrost-5-ene-16-one (10) yielded the new D-horno derivatives 12, 13 and 15. In vitro antiproliferative activity of selected compounds against three tumor cell lines (human breast ade- nocarcinoma ER+, MCF-7, human breast adenocarcinoma ER-, MDA-MB-231, prostate cancer AR-, PC-3, and normal fetal lung fibroblasts, MRC-5) was evaluated. Compounds 3 and 12 showed strong antiproliferative activity against PC-3 cells, the IC50 values being 2 mu M and 0.55 mu M, respectively. Compounds 6 (10 mu M) and 14 (9 mu M) showed moderate activity against MDA-MB-231 cells. The synthesized compounds 1-3, 5-8, 10 and 12-15 were not toxic to normal fetal lung fibroblasts cells, MRC-5. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.07.007