17-oximino-5-androsten-3β-yl chloroacetate | 1252553-10-8

• 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-oximino-5-androsten-3β-yl chloroacetate
• 英文别名: 17-Oximino-5-androsten-3beta-yl chloroacetate；[(3S,8R,9S,10R,13S,14S)-17-hydroxyimino-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] 2-chloroacetate
• CAS: 1252553-10-8
• 化学式: C₂₁H₃₀ClNO₃
• 分子量: 379.927
• InChiKey: UGAXTQYMYZQQOY-KZVLABISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  薯蓣皂素 在 甲醇 、 盐酸羟胺 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 17-oximino-5-androsten-3β-yl chloroacetate
  参考文献：
  名称：

  17-Oximino-5-androsten-3β-yl esters: synthesis, antiproliferative activity, acute toxicity, and effect on serum androgen level

  摘要：

  The 17-oximino-5-androsten-3 beta-yl esters (10a-10j) were synthesized from commercially available (25R)-5-Spirosten-3 beta-ol (Diosgenin) (4) as starting material. The synthesized compounds were evaluated for their antiproliferative activity against prostate specific cancer cell line DU-145, acute toxicity, and effect on serum androgen level and were compared with Finasteride used as positive control. Some of the compounds exhibited better cytotoxicity and antiandrogenic activity than the reference control. The detailed synthesis, spectroscopic data, and biological evaluation for the synthesized compounds are reported.

  DOI：

  10.1007/s00044-010-9393-3