4-[3-((E)-3-Chloro-1-methyl-propenyl)-phenoxymethyl]-5-methyl-2-[4-(2,2,2-trifluoro-ethoxy)-phenyl]-oxazole | 1027286-99-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[3-((E)-3-Chloro-1-methyl-propenyl)-phenoxymethyl]-5-methyl-2-[4-(2,2,2-trifluoro-ethoxy)-phenyl]-oxazole
• 英文别名: 4-[[3-[(E)-4-chlorobut-2-en-2-yl]phenoxy]methyl]-5-methyl-2-[4-(2,2,2-trifluoroethoxy)phenyl]-1,3-oxazole
• CAS: 1027286-99-2
• 化学式: C₂₃H₂₁ClF₃NO₃
• 分子量: 451.873
• InChiKey: DRKLBNTWTCVQCA-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  44.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,4-恶唑烷二酮 、 4-[3-((E)-3-Chloro-1-methyl-propenyl)-phenoxymethyl]-5-methyl-2-[4-(2,2,2-trifluoro-ethoxy)-phenyl]-oxazole 在 叔丁基锂 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 (E)-5-[3-(3-{5-methyl-2-[4-(2,2,2,-trifluoro-ethoxy)-phenyl]-oxazol-4-ylmethoxy}-phenyl)-but-2-enyl]-oxazolidine-2,4-dione
  参考文献：
  名称：

  New Azolidinediones as Inhibitors of Protein Tyrosine Phosphatase 1B with Antihyperglycemic Properties

  摘要：

  Insulin resistance in the liver and peripheral tissues together with a pancreatic cell defect are the common causes of type 2 diabetes. It is now appreciated that insulin resistance can result from a defect in the insulin receptor signaling system, at a site post binding of insulin to its receptor. Protein tyrosine phosphatases (PTPases) have been shown to be negative regulators of the insulin receptor. Inhibiton of PTPase may be an effective method in the treatment of type 2 diabetes. A series of azolidinediones has been prepared as protein tyrosine phosphatase 1B (PTP1B) inhibitors. Several compounds were potent inhibitors against the recombinant rat and human PTP1B enzymes with submicromolar IC50 values. Elongated spacers between the azolidinedione moiety and the central aromatic portion of the molecule as well as hydrophobic groups at the vicinity of this aromatic region were very important to the inhibitory activity. Oxadiazolidinediones 87 and 88 and the corresponding acetic acid analogues 119 and 120 were the best h-PTP1B inhibitors with IC50 values in the range of 0.12-0.3 mu M. Several compounds normalized plasma glucose and insulin levels in the ob/ob and db/db diabetic mouse models.

  DOI：

  10.1021/jm990476x
• 作为产物：
  描述：

  4,5-Dimethyl-3-oxido-2-[4-(2,2,2-trifluoroethoxy)phenyl]-1,3-oxazol-3-ium 在 五氯化磷 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 calcium carbonate 、 三氯氧磷 作用下， 以 乙醚 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 62.5h， 生成 4-[3-((E)-3-Chloro-1-methyl-propenyl)-phenoxymethyl]-5-methyl-2-[4-(2,2,2-trifluoro-ethoxy)-phenyl]-oxazole
  参考文献：
  名称：

  New Azolidinediones as Inhibitors of Protein Tyrosine Phosphatase 1B with Antihyperglycemic Properties

  摘要：

  Insulin resistance in the liver and peripheral tissues together with a pancreatic cell defect are the common causes of type 2 diabetes. It is now appreciated that insulin resistance can result from a defect in the insulin receptor signaling system, at a site post binding of insulin to its receptor. Protein tyrosine phosphatases (PTPases) have been shown to be negative regulators of the insulin receptor. Inhibiton of PTPase may be an effective method in the treatment of type 2 diabetes. A series of azolidinediones has been prepared as protein tyrosine phosphatase 1B (PTP1B) inhibitors. Several compounds were potent inhibitors against the recombinant rat and human PTP1B enzymes with submicromolar IC50 values. Elongated spacers between the azolidinedione moiety and the central aromatic portion of the molecule as well as hydrophobic groups at the vicinity of this aromatic region were very important to the inhibitory activity. Oxadiazolidinediones 87 and 88 and the corresponding acetic acid analogues 119 and 120 were the best h-PTP1B inhibitors with IC50 values in the range of 0.12-0.3 mu M. Several compounds normalized plasma glucose and insulin levels in the ob/ob and db/db diabetic mouse models.

  DOI：

  10.1021/jm990476x