17aβ-acetoxy-16,16-dimethyl-3-methoxy-D-homo-B-nor-8-isoestra-1,3,5(10),triene | 388567-65-5

• 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: 17aβ-acetoxy-16,16-dimethyl-3-methoxy-D-homo-B-nor-8-isoestra-1,3,5(10),triene
• 英文别名: [(4S,4aS,6aS,11aS,11bS)-9-methoxy-2,2,4a-trimethyl-3,4,5,6,6a,11,11a,11b-octahydro-1H-benzo[a]fluoren-4-yl] acetate
• CAS: 388567-65-5
• 化学式: C₂₃H₃₂O₃
• 分子量: 356.505
• InChiKey: VXZKQOCCAFZYKT-KPUUQYQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17aβ-acetoxy-16,16-dimethyl-3-methoxy-D-homo-B-nor-8-isoestra-1,3,5(10),triene 在 氨 、 lithium 、 盐酸 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 16,16-dimethyl-D-homo-19,B-bisnor-8,10-isotestosterone
  参考文献：
  名称：

  Steroid 19,B-dinor-8,10-iso-analogues

  摘要：

  The Birch reduction of 3-methoxy-B-nor-8-isoestra-1,3,5(10)-trienes followed by acid hydrolysis produces steroid androgen 19,B-dinor-8,10-iso-analogues. By means of X-ray analysis and correlation NMR spectroscopy of 16,16-dimethyl-D-homo-19,B-dinor-8-isotestosterone, C20H30O2, it is demonstrated that the main conformations in the crystal and in solution for two 19,B-dinor-8,10-iso-analogues are, in general, the same.

  DOI：

  10.1107/s0108270102001002
• 作为产物：
  描述：

  17aβ-hydroxy-16,16-dimethyl-3-methoxy-D-homo-B-norestra-1,3,5(10),8,14-pentaene 在 镍 吡啶 、 氢气 作用下， 以 苯 为溶剂， 60.0~120.0 ℃ 、14.71 MPa 条件下， 反应 4.0h， 生成 17aβ-acetoxy-16,16-dimethyl-3-methoxy-D-homo-B-nor-8-isoestra-1,3,5(10),triene
  参考文献：
  名称：

  带有顺式融合的B环和C环的类固醇雄激素19，B-双歧类似物的合成

  摘要：

  Reduction by Birch procedure of 3-methoxy-B-nor-8-isoestra-1,3,5(10)-trienes followed by hydrolysis of reaction products furnished 19,B-bisnor-8,10-isoanalogs of steroid androgens. With the use of the correlation NMR spectroscopy a complete assignment of signals in the H-1 and C-13 NMR spectra was performed for two representatives of this steroid group, and their prevailing conformations in solution were established.

  DOI：

  10.1023/a:1012401312741

文献信息

• Molecular structure and biological properties of some 16,16-dimethyl-D-homo-B-nor-9β analogs of steroid estrogens
  作者：S. N. Morozkina、G. L. Starova、S. I. Selivanov、A. G. Shavva

  DOI：10.1134/s107036321106020x

  日期：2011.6

  perform docking of a series of D-homo-B-nor-9β-estra-1,3,5(10)-trienes to hormone-binding pocket of estrogen α-receptors, and 16,16-dimethyl-D-homo-B-nor-9-estrone was selected for studying its biological properties. This compound was found to possess cardioprotective activity and no uterotropic effect.

  由X射线衍射数据确定的17aβ-乙酰氧基-16,16-二甲基-3-甲氧基-D-高纯-Bnor-9β-estra-1,3,5（10）-三烯分子中的质子距离并且通过1 H NMR光谱与从头算以及通过PM3和MM +方法计算的结果一致。因此，MM +计算用于将一系列D-homo-B-nor-9β-estra-1,3,5（10）-三烯对接至雌激素α-受体的荷尔蒙结合口袋和16,16选择了-二甲基-D-同型-B-nor-9-雌酮来研究其生物学特性。发现该化合物具有心脏保护活性并且没有促子宫作用。