[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-[[hydroxy-[hydroxy-[[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]oxy]phosphoryl]oxyphosphoryl]oxymethyl]-4-[(4-methoxyphenyl)methoxy]oxolan-3-yl] dibenzyl phosphate | 478050-96-3

• 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: [(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-[[hydroxy-[hydroxy-[[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]oxy]phosphoryl]oxyphosphoryl]oxymethyl]-4-[(4-methoxyphenyl)methoxy]oxolan-3-yl] dibenzyl phosphate
• CAS: 478050-96-3
• 化学式: C₅₀H₅₆N₅O₁₅P₃
• 分子量: 1059.94
• InChiKey: BRFSWYMLEDXPCT-IFDZFPEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  73
• 可旋转键数：
  20
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  261
• 氢给体数：
  3
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-[[hydroxy-[hydroxy-[[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]oxy]phosphoryl]oxyphosphoryl]oxymethyl]-4-[(4-methoxyphenyl)methoxy]oxolan-3-yl] dibenzyl phosphate 在 10percent Pd/C 氢气 作用下， 以 水 为溶剂， 反应 6.0h， 以52%的产率得到3'-phosphoadenosine 5'-diphospho-(3-estrone)
  参考文献：
  名称：

  Synthesis of a Bisubstrate Analogue Targeting Estrogen Sulfotransferase

  摘要：

  Sulfotransferases catalyze the transfer of a sulfuryl group from the eukaryotic sulfate donor X-phosphoadenosine 5'-phosphosulfate to an acceptor biomolecule. Sulfotransferases have been linked with several disease states, prompting our investigation of specific sulfotransferase inhibitors. Presented herein is the synthesis and evaluation of a bisubstrate analogue designed to inhibit estrogen sulfotransferase. The synthesis utilizes a novel, orthogonally protected X-phosphoadenosine 5'-phosphate (PAP) derivative allowing the selective functionalization of the 5'-phosphate with a sulfate acceptor mimic. Kinetic studies revealed significant inhibitory activity and provide guidance for improved inhibitor design.

  DOI：

  10.1021/jo0260443
• 作为产物：
  描述：

  estra-1,3,5(10)-trien-17-one-3-phosphate disodium salt 、 3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)-5'-O-phosphate adenosine 在 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 以43%的产率得到[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-[[hydroxy-[hydroxy-[[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]oxy]phosphoryl]oxyphosphoryl]oxymethyl]-4-[(4-methoxyphenyl)methoxy]oxolan-3-yl] dibenzyl phosphate
  参考文献：
  名称：

  Synthesis of a Bisubstrate Analogue Targeting Estrogen Sulfotransferase

  摘要：

  Sulfotransferases catalyze the transfer of a sulfuryl group from the eukaryotic sulfate donor X-phosphoadenosine 5'-phosphosulfate to an acceptor biomolecule. Sulfotransferases have been linked with several disease states, prompting our investigation of specific sulfotransferase inhibitors. Presented herein is the synthesis and evaluation of a bisubstrate analogue designed to inhibit estrogen sulfotransferase. The synthesis utilizes a novel, orthogonally protected X-phosphoadenosine 5'-phosphate (PAP) derivative allowing the selective functionalization of the 5'-phosphate with a sulfate acceptor mimic. Kinetic studies revealed significant inhibitory activity and provide guidance for improved inhibitor design.

  DOI：

  10.1021/jo0260443