2-<(5-methyl-2-phenyl-4-oxazolyl)methyl>benzofuran-5-carbonitrile | 132646-33-4

• 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-phenyl-4-oxazolyl)methyl>benzofuran-5-carbonitrile
• 英文别名: 2-(2-Phenyl-5-methyloxazol-4-ylmethyl)-5-cyanobenzofuran；5-Benzo[b]furancarbonitrile,2-[(5-methyl-2-phenyl-4-oxazolyl)methyl]-；2-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]-1-benzofuran-5-carbonitrile
• CAS: 132646-33-4
• 化学式: C₂₀H₁₄N₂O₂
• 分子量: 314.343
• InChiKey: IAFUCKKYKFDKIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  139-140 °C
• 沸点：
  512.4±60.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 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：
  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-phenyl-4-oxazolyl)methyl>benzofuran-5-carbonitrile 在 nickel-aluminum alloy 、 jones reagent 作用下， 以 甲酸 、 乙醚 、 丙酮 为溶剂， 生成 1-[2-(5-methyl-2-phenyloxazol-4-ylmethyl)benzofuran-5-yl]ethanone
  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
• 作为产物：
  描述：

  (5-溴-1-苯并呋喃-2-基)-(5-甲基-2-苯基-1,3-恶唑-4-基)甲酮 在 三乙基硅烷 、 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 2-<(5-methyl-2-phenyl-4-oxazolyl)methyl>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

• Oxazolidinedione hypoglycemic agents
  申请人：Pfizer Inc.

  公开号：US05498621A1

  公开（公告）日：1996-03-12

  Compounds of the formulae ##STR1## where R is cycloalkyl or aryl; R.sub.1 is alkyl, X is O or C.dbd.O; A is O or S; and B is N or CH are useful as hypoglycemic agents.

  式##STR1##中R为环烷基或芳基；R.sub.1为烷基，X为O或C.dbd.O；A为O或S；B为N或CH的化合物可用作降糖药。
• 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：——
• HYPOGLYCEMIC HYDROXYUREA DERIVATIVES
  申请人：PFIZER INC.

  公开号：EP0544696B1

  公开（公告）日：1995-01-11
• US5334604A
  申请人：——

  公开号：US5334604A

  公开（公告）日：1994-08-02
• US5463070A
  申请人：——

  公开号：US5463070A

  公开（公告）日：1995-10-31