N-[4-[(4-acetamidophenoxy)-[2-[(2S,3R)-2-amino-3-methylpentanoyl]-1,3-dihydroisoindol-1-yl]phosphoryl]oxyphenyl]acetamide;2,2,2-trifluoroacetic acid | 960300-54-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[4-[(4-acetamidophenoxy)-[2-[(2S,3R)-2-amino-3-methylpentanoyl]-1,3-dihydroisoindol-1-yl]phosphoryl]oxyphenyl]acetamide;2,2,2-trifluoroacetic acid
• CAS: 960300-54-3
• 化学式: C₂HF₃O₂*C₃₀H₃₅N₄O₆P
• 分子量: 692.629
• InChiKey: KPIGIJVXQQJEID-YKRGQPKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  48
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  177
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  tert-butyl (2S,3R)-1-(1-(di(4-acetamidophenoxy)phosphoryl)isoindolin-2-yl)-3-methyl-1-oxopentan-2-ylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以96%的产率得到N-[4-[(4-acetamidophenoxy)-[2-[(2S,3R)-2-amino-3-methylpentanoyl]-1,3-dihydroisoindol-1-yl]phosphoryl]oxyphenyl]acetamide;2,2,2-trifluoroacetic acid
  参考文献：
  名称：

  Irreversible Inhibition of Dipeptidyl Peptidase 8 by Dipeptide-Derived Diaryl Phosphonates

  摘要：

  Dipeptide-derived compounds, bearing various P2 residues and a diaryl pyrrolidin-2-yl phosphonate at the PI position, were evaluated as dipeptidyl peptidase 8 (DPP8) inhibitors. With these products, irreversible inhibition of DPP8 was observed. To obtain inhibitors with an improved activity and selectivity profile, a set of selected analogues containing a diaryl isoindolin-1-ylphosphonate at P1 was synthesized and evaluated. Within this latter series, compound 2e was shown to be a potent, irreversible inhibitor of DPP8, demonstrating very low affinity for DPP IV and DPP II.

  DOI：

  10.1021/jm701005a