N-[[3-[[2-[3,5-bis(trifluoromethyl)phenyl]-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]methyl]hydroxylamine | 1026732-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-[[3-[[2-[3,5-bis(trifluoromethyl)phenyl]-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]methyl]hydroxylamine
• CAS: 1026732-83-1
• 化学式: C₂₀H₁₆F₆N₂O₃
• 分子量: 446.349
• InChiKey: FWMGWUKIFXVTBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-(氯甲酰)异氰酸酯 、 N-[[3-[[2-[3,5-bis(trifluoromethyl)phenyl]-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]methyl]hydroxylamine 以 四氢呋喃 为溶剂， 生成 2-[[3-[[2-[3,5-Bis(trifluoromethyl)phenyl]-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]methyl]-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-[[2-[3,5-Bis(trifluoromethyl)phenyl]-5-methyl-1,3-oxazol-4-yl]methoxy]benzaldehyde 在 盐酸 、 盐酸羟胺 、 sodium acetate 、 methyl orange 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 生成 N-[[3-[[2-[3,5-bis(trifluoromethyl)phenyl]-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]methyl]hydroxylamine
  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

• Azole Phenoxy Hydroxyureas as Selective and Orally Active Inhibitors of 5-Lipoxygenase
  作者：Michael S. Malamas、Richard P. Carlson、David Grimes、Ralph Howell、Keith Glaser、Iwan Gunawan、James A. Nelson、Mira Kanzelberger、Uresh Shah、David A. Hartman

  DOI：10.1021/jm950363n

  日期：1996.1.1

  demonstrated high and selective 5-LO inhibitory activity in the in vitro assays, with IC50 values ranging from 0.08 microM in mouse macrophages to 0.8 microM in human peripheral monocytes to 1.2 microM in human whole blood. This activity was selective for 5-LO, as concentrations up to 15 microM in mouse macrophages did not affect prostaglandin formation. Oxazole 59 was the most active inhibitor in the human

  唑类苯氧基羟基脲是一类新的5-脂氧合酶（5-LO）抑制剂。结构-活性关系研究表明，恶唑尾巴的2-苯基部分的负电取代基增加了这些抑制剂的离体效能。噻唑类似物上的类似取代对离体活性仅有很小的贡献。三氟甲基取代的恶唑24是离体（6 h预处理大鼠）和体内（3 h预处理大鼠）RPAR测定中最佳恶唑系列化合物，ED50值分别约为1和3.6 mg / kg，但在过敏性豚鼠试验中的活性较弱。恶唑50在RPAR和豚鼠体内模型中均具有同等活性，与齐留通相似。未取代的噻唑52是噻唑系列中最好的化合物，在口服剂量为10 mg / kg的情况下，通过抑制RPAR分析（预处理3小时的大鼠）中白三烯B4的生物合成为99％，而在静脉注射剂量为10 mg / kg的情况下，对变应性豚鼠的支气管收缩作用抑制了50％公斤。在体外测定中，恶唑24表现出高选择性的5-LO抑制活性，IC50值范围从小鼠巨噬细胞中的0.08 microM到人外周单核细胞中的0