5-(2-benzyloxy-4-fluorophenyl)furan-2-carbaldehyde | 900515-32-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(2-benzyloxy-4-fluorophenyl)furan-2-carbaldehyde
• CAS: 900515-32-4
• 化学式: C₁₈H₁₃FO₃
• 分子量: 296.298
• InChiKey: JIZPHVAETWHUNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  39.44
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(2-benzyloxy-4-fluorophenyl)furan-2-carbaldehyde 在 三氯化硼 、 溶剂黄146 、 β-丙氨酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 5-[[5-(4-氟-2-羟基苯基)-2-呋喃基]亚甲基]-2,4-噻唑烷二酮
  参考文献：
  名称：

  Furan-2-ylmethylene Thiazolidinediones as Novel, Potent, and Selective Inhibitors of Phosphoinositide 3-Kinase γ

  摘要：

  Class I phosphoinositide 3-kinases (PI3Ks), in particular PI3K gamma, have become attractive drug targets for inflammatory and autoimmune diseases. Here, we disclose a novel series of furan-2-ylmethylene thiazolidinediones as selective, ATP-competitive PI3K gamma inhibitors. Structure-based design and X-ray crystallography of complexes formed by inhibitors bound to PI3K gamma identified key pharmacophore features for potency and selectivity. An acidic NH group on the thiazolidinedione moiety and a hydroxy group on the furan-2-yl-phenyl part of the molecule play crucial roles in binding to PI3K and contribute to class IB PI3K selectivity. Compound 26 (AS-252424), a potent and selective small-molecule PI3K gamma inhibitor emerging from these efforts, was further profiled in three different cellular PI3K assays and shown to be selective for class IB PI3K-mediated cellular effects. Oral administration of 26 in a mouse model of acute peritonitis led to a significant reduction of leukocyte recruitment.

  DOI：

  10.1021/jm0601598
• 作为产物：
  描述：

  2-溴-5-氟苯酚 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 16.0h， 生成 5-(2-benzyloxy-4-fluorophenyl)furan-2-carbaldehyde
  参考文献：
  名称：

  Furan-2-ylmethylene Thiazolidinediones as Novel, Potent, and Selective Inhibitors of Phosphoinositide 3-Kinase γ

  摘要：

  Class I phosphoinositide 3-kinases (PI3Ks), in particular PI3K gamma, have become attractive drug targets for inflammatory and autoimmune diseases. Here, we disclose a novel series of furan-2-ylmethylene thiazolidinediones as selective, ATP-competitive PI3K gamma inhibitors. Structure-based design and X-ray crystallography of complexes formed by inhibitors bound to PI3K gamma identified key pharmacophore features for potency and selectivity. An acidic NH group on the thiazolidinedione moiety and a hydroxy group on the furan-2-yl-phenyl part of the molecule play crucial roles in binding to PI3K and contribute to class IB PI3K selectivity. Compound 26 (AS-252424), a potent and selective small-molecule PI3K gamma inhibitor emerging from these efforts, was further profiled in three different cellular PI3K assays and shown to be selective for class IB PI3K-mediated cellular effects. Oral administration of 26 in a mouse model of acute peritonitis led to a significant reduction of leukocyte recruitment.

  DOI：

  10.1021/jm0601598