3-Chloromethyl-5-(4-trifluoromethoxy-phenyl)-[1,2,4]oxadiazole | 166179-22-2

• 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-Chloromethyl-5-(4-trifluoromethoxy-phenyl)-[1,2,4]oxadiazole
• 英文别名: 3-(Chloromethyl)-5-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole；3-(chloromethyl)-5-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole
• CAS: 166179-22-2
• 化学式: C₁₀H₆ClF₃N₂O₂
• mdl: MFCD09859901
• 分子量: 278.618
• InChiKey: FXYFIRQTCCDGPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  48.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-Chloromethyl-5-(4-trifluoromethoxy-phenyl)-[1,2,4]oxadiazole 在 盐酸 、 盐酸羟胺 、 sodium acetate 、 methyl orange 、 sodium cyanoborohydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 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：

  4-(三氟甲氧基)苯甲酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 48.0h， 生成 3-Chloromethyl-5-(4-trifluoromethoxy-phenyl)-[1,2,4]oxadiazole
  参考文献：
  名称：

  CVT-4325: a potent fatty acid oxidation inhibitor with favorable oral bioavailability

  摘要：

  New inhibitors of palmitoyl-CoA oxidation are based on the introduction of nitrogen heterocycles in the 'Western Portion' of the molecule. SAR studies led to the discovery of CVT-4325 (shown), a potent FOXi (IC50 = 380 nM rat mitochondria) with favorable PK properties (F= 93%, t(1/2) = 13.6 h, dog). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.077