3β-hydroxy-D-homo-16-amino-17-phenyl-5,16-androstadien-17a-one | 220426-69-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3β-hydroxy-D-homo-16-amino-17-phenyl-5,16-androstadien-17a-one
• 英文别名: (4aS,4bR,8S,10aR,10bS,12aS)-3-amino-8-hydroxy-10a,12a-dimethyl-2-phenyl-4a,4b,5,7,8,9,10,10b,11,12-decahydro-4H-chrysen-1-one
• CAS: 220426-69-7
• 化学式: C₂₆H₃₃NO₂
• 分子量: 391.554
• InChiKey: WXCXXHGXGJZCIY-QRDUSVRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3β-hydroxy-D-homo-16-amino-17-phenyl-5,16-androstadien-17a-one 以 吡啶 为溶剂， 反应 20.0h， 以73%的产率得到3β-acetoxy-D-homo-16-amino-17-phenyl-5,16-androstadien-17a-one
  参考文献：
  名称：

  Synthesis, X-ray crystal structures and biological activity of 16-amino-17-substituted-D-homo steroid derivatives

  摘要：

  Homo derivatives in the androstane and estrane series, 12-19, were synthesized by a fragmentation-cyclization reaction of 16-oximino-17-hydroxy-17-substituted derivatives 3-9, or by cyclization of the corresponding D-seco derivatives 20-26. The structures were confirmed by X-ray analysis of compounds 12 and 16. Preliminary assessment of inhibitory effects of D-homo derivatives from androstane series towards aromatase, 3beta-hydroxysteroid dehydrogenase (3beta-HSD), 17alpha-hydroxylase/C17-20 lyase (P450c17) and 17beta-HSD indicated much lower inhibitory potential compared to previously tested activity of another type of D-modified steroids, namely D-seco derivatives. Also, assessment of potential antiestrogenic activity of derivatives from estrane series showed absence of such an activity. (C) 2003 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(03)00097-7
• 作为产物：
  描述：

  3β-hydroxy-16-oximino-5-androsten-17-one 在 氢氧化钾 、 lithium 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙二醇 为溶剂， 反应 5.0h， 生成 3β-hydroxy-D-homo-16-amino-17-phenyl-5,16-androstadien-17a-one
  参考文献：
  名称：

  Synthesis, X-ray crystal structures and biological activity of 16-amino-17-substituted-D-homo steroid derivatives

  摘要：

  Homo derivatives in the androstane and estrane series, 12-19, were synthesized by a fragmentation-cyclization reaction of 16-oximino-17-hydroxy-17-substituted derivatives 3-9, or by cyclization of the corresponding D-seco derivatives 20-26. The structures were confirmed by X-ray analysis of compounds 12 and 16. Preliminary assessment of inhibitory effects of D-homo derivatives from androstane series towards aromatase, 3beta-hydroxysteroid dehydrogenase (3beta-HSD), 17alpha-hydroxylase/C17-20 lyase (P450c17) and 17beta-HSD indicated much lower inhibitory potential compared to previously tested activity of another type of D-modified steroids, namely D-seco derivatives. Also, assessment of potential antiestrogenic activity of derivatives from estrane series showed absence of such an activity. (C) 2003 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(03)00097-7

文献信息

• A novel fragmentation-cyclization reaction of steroidal α-hydroxy oximes
  作者：Katarina Penov-Gaši、Dušan Miljković、Ljubica Medić-Mijačević、Evgenija Durendić、Julijana Petrović、Vjera Pejanović、Slobodanka Stanković、Dušan Lazar

  DOI：10.1016/s0040-4039(98)02166-2

  日期：1998.12

  By a novel “one pot” fragmentation-cyclization reaction 17β-hydroxy-17α-substituted-16-oximino derivatives in the androstane and estrane series were converted to a new type of D-homo derivative.

  通过新颖的“一锅”裂解-环化反应，雄甾烷和雌激素系列中的17β-羟基-17α-取代的16-肟基衍生物被转化为新型的D-homo衍生物。