(5-溴-1-苯并呋喃-2-基)-(5-甲基-2-苯基-1,3-恶唑-4-基)甲酮 | 132646-31-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (5-溴-1-苯并呋喃-2-基)-(5-甲基-2-苯基-1,3-恶唑-4-基)甲酮
• 英文名称: (5-bromo-2-benzofuranyl)(5-methyl-2-phenyl-4-oxazolyl)methanone
• 英文别名: 2-(2-Phenyl-5-methyloxazol-4-ylcarbonyl)-5-bromobenzofuran；Methanone, (5-bromo-2-benzofuranyl)(5-methyl-2-phenyl-4-oxazolyl)-；(5-bromo-1-benzofuran-2-yl)-(5-methyl-2-phenyl-1,3-oxazol-4-yl)methanone
• CAS: 132646-31-2
• 化学式: C₁₉H₁₂BrNO₃
• 分子量: 382.213
• InChiKey: CXYDSMNJLLVBPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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-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 、 二氯甲烷 为溶剂， 生成 (5-bromo-2-benzofuranyl)(5-methyl-2-phenyl-4-oxazolyl)methane
  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：

  2-溴-1-(5-甲基-2-苯基-1,3-恶唑-4-基)乙酮 、 5-溴水杨醛 在 sodium methylate 作用下， 以 乙醇 为溶剂， 以53%的产率得到(5-溴-1-苯并呋喃-2-基)-(5-甲基-2-苯基-1,3-恶唑-4-基)甲酮
  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

• Hypoglycemic hydroxyurea derivatives
  申请人：Pfizer Inc.

  公开号：US05463070A1

  公开（公告）日：1995-10-31

  Certain 1-(benzyl or 5-benzofuranylmethyl)-1-hydroxyurea derivatives are useful as hypoglycemic and hypocholesterolemic agents.

  某些1-(苄基或5-苯并呋喃基甲基)-1-羟基脲衍生物可用作降血糖和降胆固醇剂。
• 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
• THIAZOLIDINEDIONE HYPOGLYCEMIC AGENTS
  申请人：PFIZER INC.

  公开号：EP0591252B1

  公开（公告）日：1996-09-11
• US5334604A
  申请人：——

  公开号：US5334604A

  公开（公告）日：1994-08-02