2-[[5-Methyl-2-(3-methylphenyl)-1,3-oxazol-4-yl]methyl]-1-benzofuran-5-carbonitrile | 136058-85-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[[5-Methyl-2-(3-methylphenyl)-1,3-oxazol-4-yl]methyl]-1-benzofuran-5-carbonitrile
• CAS: 136058-85-0
• 化学式: C₂₁H₁₆N₂O₂
• 分子量: 328.37
• InChiKey: JFVYEDZHEDTKDO-UHFFFAOYSA-N

物化性质

• 沸点：
  529.0±60.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  63
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[[5-Methyl-2-(3-methylphenyl)-1,3-oxazol-4-yl]methyl]-1-benzofuran-5-carbonitrile 在 palladium on activated charcoal 甲酸 、 aluminum nickel 、 氢气 、 sodium acetate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 25.0~120.0 ℃ 、275.79 kPa 条件下， 反应 6.0h， 生成 5-[[2-[[5-Methyl-2-(3-methylphenyl)-1,3-oxazol-4-yl]methyl]-1-benzofuran-5-yl]methyl]-1,3-oxazolidine-2,4-dione
  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：

  在 三乙基硅烷 、 sodium tetrahydroborate 、 sodium methylate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 2-[[5-Methyl-2-(3-methylphenyl)-1,3-oxazol-4-yl]methyl]-1-benzofuran-5-carbonitrile
  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

文献信息

• Antihyperglycemic activity of new 1,2,4-oxadiazolidine-3,5-diones
  作者：M Malamas

  DOI：10.1016/s0223-5234(00)01191-0

  日期：2001.1

  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.
• DOW, ROBERT L.;BECHLE, BRUCE M.;CHOU, THOMAS T.;CLARK, DAVID A.;HULIN, BE+, J. MED. CHEM., 34,(1991) N, C. 1538-1544
  作者：DOW, ROBERT L.、BECHLE, BRUCE M.、CHOU, THOMAS T.、CLARK, DAVID A.、HULIN, BE+

  DOI：——

  日期：——