3-[[di(propan-2-yl)amino]-[2-(6-methoxy-7-methyl-3-oxo-4-phenylmethoxy-1H-2-benzofuran-5-yl)ethoxy]phosphanyl]oxypropanenitrile | 909420-47-9

• 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: 3-[[di(propan-2-yl)amino]-[2-(6-methoxy-7-methyl-3-oxo-4-phenylmethoxy-1H-2-benzofuran-5-yl)ethoxy]phosphanyl]oxypropanenitrile
• CAS: 909420-47-9
• 化学式: C₂₈H₃₇N₂O₆P
• 分子量: 528.585
• InChiKey: JJSWBZXISWBDTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  90.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-[[di(propan-2-yl)amino]-[2-(6-methoxy-7-methyl-3-oxo-4-phenylmethoxy-1H-2-benzofuran-5-yl)ethoxy]phosphanyl]oxypropanenitrile 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-[7-hydroxy-6-(ethyl-2-yl)-5-methoxy-4-methylphthalan-1-one]methylenephospho-P²-(adenosin-5'-yl)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：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 7-benzyloxy-6-(2-hydroxyethyl)-5-methoxy-4-methylphthalan-1-one 以 乙腈 为溶剂， 生成 3-[[di(propan-2-yl)amino]-[2-(6-methoxy-7-methyl-3-oxo-4-phenylmethoxy-1H-2-benzofuran-5-yl)ethoxy]phosphanyl]oxypropanenitrile
  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

文献信息

• Novel Methylenephosphophosphonate Analogues of Mycophenolic Adenine Dinucleotide. Inhibition of Inosine Monophosphate Dehydrogenase
  作者：Dominik Rejman、Magda Olesiak、Liqiang Chen、Steven E. Patterson、Daniel Wilson、Hiramagalur N. Jayaram、Lizbeth Hedstrom、Krzysztof W. Pankiewicz

  DOI：10.1021/jm060479r

  日期：2006.8.1

  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.