(4aS,4bR,10aR,10bS,12aS)-6,8-bis(hydroxyimino)-10a,12a-dimethylhexadecahydronaphtho[2,1-f]quinolin-2(1H)-one | 1313612-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉类
• 英文名称: (4aS,4bR,10aR,10bS,12aS)-6,8-bis(hydroxyimino)-10a,12a-dimethylhexadecahydronaphtho[2,1-f]quinolin-2(1H)-one
• CAS: 1313612-39-3
• 化学式: C₁₉H₂₉N₃O₃
• 分子量: 347.458
• InChiKey: WWRFWQRYZRAEGQ-NUVVNAFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  25.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  94.28
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3β-acetoxy-androst-5-en-17-one oxime 在 sodium tetrahydroborate 、 Jones reagent 、 氯化亚砜 、 nickel(II) chloride hexahydrate 、 盐酸羟胺 、 sodium acetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 丙酮 为溶剂， 反应 8.5h， 生成 (4aS,4bR,10aR,10bS,12aS)-6,8-bis(hydroxyimino)-10a,12a-dimethylhexadecahydronaphtho[2,1-f]quinolin-2(1H)-one
  参考文献：
  名称：

  Synthesis and cytotoxicity of 17a-aza-d-homo-androster-17-one derivatives

  摘要：

  A series of 17a-aza-D-homo-andrester-17-one derivatives, bearing hydroxyl, hydroximino, carbonyl and thiosemicarbazido groups at the position-3 or position-6 of steroidal nucleus, were prepared and evaluated in vitro against two human cell lines (Hela (human cervical carcinoma) and SMMC 7404 (human liver carcinoma)). The results showed that these compounds could exhibit a high cytotoxicity to Hela tumor cell line, especially for compounds 8 and 12, the IC50 values are 15.1 and 14.0 nmol/mL, respectively. Our findings could provide new evidence showing the relationship between the chemical structure and biological activity and may be useful for the discovery of new anti-cancer drugs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.093