(8R,9S,13S,14S)-4-bromo-13-methyl-3-phenylmethoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one | 959393-65-8

• 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: (8R,9S,13S,14S)-4-bromo-13-methyl-3-phenylmethoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 959393-65-8
• 化学式: C₂₅H₂₇BrO₂
• 分子量: 439.392
• InChiKey: GYIOTZZAQSLOSZ-KNPBPUNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8R,9S,13S,14S)-4-bromo-13-methyl-3-phenylmethoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one 、 雌二醇 在 4-甲基吡啶 、 copper(II) oxide 作用下， 反应 72.0h， 生成 (8R,9S,13S,14S)-4-[[(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]oxy]-13-methyl-3-phenylmethoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
  参考文献：
  名称：

  Chemical Synthesis of Six Novel 17β-Estradiol and Estrone Dimers and Study of Their Formation Catalyzed by Human Cytochrome P450 Isoforms

  摘要：

  Our earlier studies have shown that over 20 nonpolar 17 beta-estradiol metabolite peaks were detected following incubations of radioactive 17 beta-estradiol with human liver microsomes or recombinant human cytochrome P450 isoforms in the presence of NADPH as a cofactor. The structures of two representative nonpolar metabolites were identified earlier as dimers of 17 beta-estradiol linked through a diaryl ether bond between the C-3 phenolic oxygen of one molecule and the C-2 or C-4 aromatic carbon of another. Six additional putative dimers between estrone and 17 beta-estradiol with structures similar to the two identified ones were synthesized in this study. Using these newly synthesized estrogen dimers as reference standards, we demonstrated that incubations of human liver microsomes or various human cytochrome P450 isoforms with estrone or 17-estradiol alone or two estrogens in combination in the presence of NADPH as a cofactor resulted in the formation of all eight estrogen dimers in varying quantities.

  DOI：

  10.1021/jm0707323
• 作为产物：
  描述：

  4-溴雌酮 、 溴甲苯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 (8R,9S,13S,14S)-4-bromo-13-methyl-3-phenylmethoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
  参考文献：
  名称：

  Chemical Synthesis of Six Novel 17β-Estradiol and Estrone Dimers and Study of Their Formation Catalyzed by Human Cytochrome P450 Isoforms

  摘要：

  Our earlier studies have shown that over 20 nonpolar 17 beta-estradiol metabolite peaks were detected following incubations of radioactive 17 beta-estradiol with human liver microsomes or recombinant human cytochrome P450 isoforms in the presence of NADPH as a cofactor. The structures of two representative nonpolar metabolites were identified earlier as dimers of 17 beta-estradiol linked through a diaryl ether bond between the C-3 phenolic oxygen of one molecule and the C-2 or C-4 aromatic carbon of another. Six additional putative dimers between estrone and 17 beta-estradiol with structures similar to the two identified ones were synthesized in this study. Using these newly synthesized estrogen dimers as reference standards, we demonstrated that incubations of human liver microsomes or various human cytochrome P450 isoforms with estrone or 17-estradiol alone or two estrogens in combination in the presence of NADPH as a cofactor resulted in the formation of all eight estrogen dimers in varying quantities.

  DOI：

  10.1021/jm0707323