(5-bromo-1-benzofuran-2-yl)[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methanone | 344900-02-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (5-bromo-1-benzofuran-2-yl)[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methanone
• 英文别名: (5-Bromo-1-benzofuran-2-yl)-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methanone
• CAS: 344900-02-3
• 化学式: C₂₀H₁₄BrNO₃
• 分子量: 396.24
• InChiKey: YAEGTSMIJAAFOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  56.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5-bromo-1-benzofuran-2-yl)[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methanone 在 三乙基硅烷 、 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 4-[(5-bromo-1-benzofuran-2-yl)methyl]-5-methyl-2-(4-methylphenyl)-1,3-oxazole
  参考文献：
  名称：

  Benzyloxazolidine-2,4-diones as potent hypoglycemic agents

  摘要：

  A series of benzyloxazolidine-2,4-diones, containing oxazole-based side chains, were found to lower blood glucose levels in the genetically obese ob/ob mouse. Incorporation of a benzofuran structural element in these compounds provides greatly enhanced in vivo potency. The syntheses and structure-activity relationships for this series are detailed.

  DOI：

  10.1021/jm00109a003
• 作为产物：
  描述：

  2-bromo-1-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]-1-ethanone 、 5-溴水杨醛 在 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 12.33h， 以78%的产率得到(5-bromo-1-benzofuran-2-yl)[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methanone
  参考文献：
  名称：

  Antihyperglycemic activity of new 1,2,4-oxadiazolidine-3,5-diones

  摘要：

  A series of 1,2,4-oxadiazolidine-3,5-diones was synthesized and evaluated as oral antihyperglycemic agents in the obese insulin resistant db/db and ob/ob mouse - the two models for Type 2 diabetes mellitus. The majority of the prepared methoxy- and ethoxy-linked oxazole 1,2,4-oxadiazolidine-3,5-diones normalized plasma glucose levels at the 100 mg kg(-1) oral dose in the db/db diabetic mouse model, and several amongst them reduced the glucose levels at the 20 mg kg(-1) oral dose. The most potent compounds in the db/db mouse model were also active in the ob/ob mouse model normalizing the plasma glucose levels at the 20 mg kg(-1) oral dose. The trifluoromethoxy analog 32 was the most active compound of the series, reducing significantly the plasma glucose levels at the 5 mg kg(-1) oral dose. Oxadiazole-tailed 1,2,4-oxadiazolidine-3,5-diones were also active in both the db/db and ob/ob diabetic mouse models normalizing plasma glucose levels at the 100 mg kg(-1) oral dose. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01191-0