10β-(1'-azirinyl)-3β,17β-dihydroxyestr-5-en | 174914-70-6

• 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: 10β-(1'-azirinyl)-3β,17β-dihydroxyestr-5-en
• 英文别名: (3S,8R,9S,10S,13S,14S,17S)-10-(2H-azirin-3-yl)-13-methyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 174914-70-6
• 化学式: C₂₀H₂₉NO₂
• 分子量: 315.456
• InChiKey: SKJUYCQJBYZPKD-IMDGIPCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10β-(1'-azirinyl)-3β,17β-dihydroxyestr-5-en 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以80%的产率得到10β-(1'-azirinyl)-3β-hydroxyestr-5-en-17-one
  参考文献：
  名称：

  Synthesis of 10β-(1′-azirinyl)estr-4-en-3,17-dione as an aromatase inhibitor

  摘要：

  The novel 10 beta-(1'-azirinyl)estr-4-en-3,17-dione (10) has been synthesized from 19-methyl-19-methiodide salt intermediates 15 and 16 by a modified Neber reaction. Four other hitherto undescribed 10 beta-1'-azirinyl steroids 9, 12, 17, and 18 were also synthesized. Compound 10 inhibited human placental aromatase in vitro (IC50 value = 5.5 mu M) but was not as potent as the related (19R)-10 beta-aziridine (1).

  DOI：

  10.1016/0039-128x(95)00217-e
• 作为产物：
  描述：

  19-Methyl-19-oxoandrost-5-ene-3β,17β-diyl bis(tert-butyldimethylsilyl ether) 在 氢氟酸 、 sodium hydride 、 二甲基亚砜 、 三氟乙酸 作用下， 以 乙醇 、 甲苯 、 乙腈 、 paraffin 、 苯 为溶剂， 反应 116.0h， 生成 10β-(1'-azirinyl)-3β,17β-dihydroxyestr-5-en
  参考文献：
  名称：

  Synthesis of 10β-(1′-azirinyl)estr-4-en-3,17-dione as an aromatase inhibitor

  摘要：

  The novel 10 beta-(1'-azirinyl)estr-4-en-3,17-dione (10) has been synthesized from 19-methyl-19-methiodide salt intermediates 15 and 16 by a modified Neber reaction. Four other hitherto undescribed 10 beta-1'-azirinyl steroids 9, 12, 17, and 18 were also synthesized. Compound 10 inhibited human placental aromatase in vitro (IC50 value = 5.5 mu M) but was not as potent as the related (19R)-10 beta-aziridine (1).

  DOI：

  10.1016/0039-128x(95)00217-e