N⁶-benzoyl-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine | 478050-93-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核糖核苷3'-磷酸盐
• 英文名称: N⁶-benzoyl-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine
• 英文别名: [(2R,3R,4R,5R)-5-(6-benzamidopurin-9-yl)-2-(hydroxymethyl)-4-[(4-methoxyphenyl)methoxy]oxolan-3-yl] dibenzyl phosphate
• CAS: 478050-93-0
• 化学式: C₃₉H₃₈N₅O₉P
• 分子量: 751.733
• InChiKey: GGXFAWHLYOEXSV-AQOIBLHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  54
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  165
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N⁶-benzoyl-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine 在 四氮唑 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 N⁶-benzoyl-5'-O-[bis(allyloxy)phosphoryl]-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine
  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：

  5'-O-dimethoxytrityl-2'-O-(4-methoxybenzyl)-N⁶-benzoyl adenosine 在 四氮唑 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 N⁶-benzoyl-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine
  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

文献信息

• Synthesis of a Bisubstrate Analogue Targeting Estrogen Sulfotransferase
  作者：Joshua I. Armstrong、Dawn E. Verdugo、Carolyn R. Bertozzi

  DOI：10.1021/jo0260443

  日期：2003.1.1

  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.