7-benzyloxy-6-(2-hydroxyethylbenzylhydroxymethylphosphonate)-5-methoxy-4-methylphthalan-1-one | 909420-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 7-benzyloxy-6-(2-hydroxyethylbenzylhydroxymethylphosphonate)-5-methoxy-4-methylphthalan-1-one
• 英文别名: 6-[2-[hydroxymethyl(phenylmethoxy)phosphoryl]oxyethyl]-5-methoxy-4-methyl-7-phenylmethoxy-3H-2-benzofuran-1-one
• CAS: 909420-48-0
• 化学式: C₂₇H₂₉O₈P
• 分子量: 512.496
• InChiKey: ROOSCRIYOVBCIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  7-benzyloxy-6-(2-hydroxyethylbenzylhydroxymethylphosphonate)-5-methoxy-4-methylphthalan-1-one 在 palladium on activated charcoal 四氮唑 、 氢气 、 三乙基碳酸氢铵缓冲液 作用下， 以 1,4-二氧六环 、 乙醇 、 乙腈 为溶剂， 反应 2.0h， 生成 P¹-(adenosin-5'-yl)methylenephospho-P²-[7-hydroxy-6-(ethyl-2-yl)-5-methoxy-4-methylphthalan-1-one]phosphonate bis(triethylamine)
  参考文献：
  名称：

  Novel Methylenephosphophosphonate Analogues of Mycophenolic Adenine Dinucleotide. Inhibition of Inosine Monophosphate Dehydrogenase

  摘要：

  Novel methylenephosphophosphonate analogues of mycophenolic adenine dinucleotide ( MAD) have been prepared as potential inhibitors of IMP dehydrogenase. A coupling of the mycophenolic (hydroxymethyl)phosphonate 6 with the phosphitylated adenosine analogue 11 followed by oxidation and deprotection afforded the phosphophosphonate 8. A similar coupling between adenosine ( hydroxymethyl) phosphonate 10 and phosphitylated mycophenolic alcohol 5 gave the corresponding phosphophosphonate 13. Both 8 and 13 (K-i = 20- 87 nM) were found to be the most potent cofactor type inhibitors of IMP dehydrogenase.

  DOI：

  10.1021/jm060479r
• 作为产物：
  描述：

  7-benzyloxy-6-(2-hydroxyethyl)-5-methoxy-4-methylphthalan-1-one 在 N-甲基咪唑 、 2,4,6-三异丙基苯磺酰氯 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 7-benzyloxy-6-(2-hydroxyethylbenzylhydroxymethylphosphonate)-5-methoxy-4-methylphthalan-1-one
  参考文献：
  名称：

  Novel Methylenephosphophosphonate Analogues of Mycophenolic Adenine Dinucleotide. Inhibition of Inosine Monophosphate Dehydrogenase

  摘要：

  Novel methylenephosphophosphonate analogues of mycophenolic adenine dinucleotide ( MAD) have been prepared as potential inhibitors of IMP dehydrogenase. A coupling of the mycophenolic (hydroxymethyl)phosphonate 6 with the phosphitylated adenosine analogue 11 followed by oxidation and deprotection afforded the phosphophosphonate 8. A similar coupling between adenosine ( hydroxymethyl) phosphonate 10 and phosphitylated mycophenolic alcohol 5 gave the corresponding phosphophosphonate 13. Both 8 and 13 (K-i = 20- 87 nM) were found to be the most potent cofactor type inhibitors of IMP dehydrogenase.

  DOI：

  10.1021/jm060479r