3-[5-(4-Trifluoromethoxy-phenyl)-[1,2,4]-oxadiazol-3-ylmethoxy]-benzaldehyde oxime | 166179-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-[5-(4-Trifluoromethoxy-phenyl)-[1,2,4]-oxadiazol-3-ylmethoxy]-benzaldehyde oxime
• 英文别名: N-[[3-[[5-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]phenyl]methylidene]hydroxylamine
• CAS: 166179-24-4
• 化学式: C₁₇H₁₂F₃N₃O₄
• 分子量: 379.295
• InChiKey: MXKWBQNJPQYVTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  90
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-[5-(4-Trifluoromethoxy-phenyl)-[1,2,4]-oxadiazol-3-ylmethoxy]-benzaldehyde oxime 在 盐酸 、 methyl orange 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 生成 2-{3-[5-(4-trifluoromethoxy-phenyl)-[1,2,4]oxadiazol-3-ylmethoxy]-benzyl}-[1,2,4]oxadiazolidine-3,5-dione
  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：

  3-Chloromethyl-5-(4-trifluoromethoxy-phenyl)-[1,2,4]oxadiazole 在 盐酸羟胺 、 sodium acetate 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[5-(4-Trifluoromethoxy-phenyl)-[1,2,4]-oxadiazol-3-ylmethoxy]-benzaldehyde oxime
  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

文献信息

• Di-oxadiazolidine derivatives as antihyperglycemic agents
  申请人：American Home Products Corporation

  公开号：US05420146A1

  公开（公告）日：1995-05-30

  This invention relates to novel 2-[4-(5-substituted-1,2,4-oxadiazol-3-ylmethoxy)benzyl]-1,2,5-oxadiazolidi ne-3,5-diones which have demonstrated antihyperglycemic activity in diabetic (ob/ob and db/db) mice, genetic animal models of non-insulin dependent diabetes mellitus (NIDDM or Type II diabetes). These compounds are represented by Formula I below: ##STR1## wherein R.sup.1 is C.sub.6 -C.sub.10 aryl, optionally substituted by one to three substituents independently selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, fluorine, chlorine, bromine, iodine, C.sub.1 -C.sub.3 trifluoroalkyl or C.sub.1 -C.sub.3 trifluoroalkoxy; and R.sup.2 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl, fluorine, chlorine, bromine, iodine, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.3 trifluoroalkyl, and C.sub.1 -C.sub.3 trifluoroalkoxy, or a pharmaceutically acceptable salt thereof.

  本发明涉及一种新型2-[4-(5-取代-1,2,4-噁二唑-3-基甲氧基)苯甲基]-1,2,5-噁二唑烷-3,5-二酮化合物，该化合物在糖尿病(ob/ob和db/db)小鼠中表现出抗高血糖活性，该小鼠是非胰岛素依赖性糖尿病（NIDDM或2型糖尿病）的遗传动物模型。该化合物由下式I表示：##STR1##其中R1是C6-C10芳基，可选地被一个至三个取自C1-C6烷基，C1-C6烷氧基，氟，氯，溴，碘，C1-C3三氟甲基或C1-C3三氟甲氧基的取代基独立取代；R2选自氢，C1-C6烷基，氟，氯，溴，碘，C1-C6烷氧基，C1-C3三氟甲基和C1-C3三氟甲氧基，或其药学上可接受的盐。