N-(5-ethyl-4-phenyloxazol-2-yl)-2-(3-methyl-4-oxo-3,4-dihydrophthalazin-1-yl) acetamide | 1458056-28-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-(5-ethyl-4-phenyloxazol-2-yl)-2-(3-methyl-4-oxo-3,4-dihydrophthalazin-1-yl) acetamide
• 英文别名: N-(5-ethyl-4-phenyl-1,3-oxazol-2-yl)-2-(3-methyl-4-oxophthalazin-1-yl)acetamide
• CAS: 1458056-28-4
• 化学式: C₂₂H₂₀N₄O₃
• 分子量: 388.426
• InChiKey: GIRTVDKHEZQSQQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  87.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-乙基-4-苯基-1,3-恶唑-2-胺 、 2-(4-氧-3,4-二氢邻苯二甲秦)乙酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 49.0h， 以43%的产率得到N-(5-ethyl-4-phenyloxazol-2-yl)-2-(3-methyl-4-oxo-3,4-dihydrophthalazin-1-yl) acetamide
  参考文献：
  名称：

  Discovery of thiazolyl-phthalazinone acetamides as potent glucose uptake activators via high-throughput screening

  摘要：

  With the aim to discover orally active small molecules that stimulate glucose uptake, high throughput screening of a library of 5000 drug-like compounds was conducted in differentiated skeletal muscle cells in presence of insulin. N-Substituted phthalazinone acetamide was identified as a potential glucose uptake modulator. Several novel derivatives were synthesized to establish structure activity relationships. Identified lead thiazolyl-phthalazinone acetamide (7114863) increased glucose uptake (EC50 of 0.07 +/- 0.02 mu M) in differentiated skeletal muscle cells in presence of insulin. Furthermore, 7114863 was superior to rosiglitazone under similar experimental conditions without inducing PPAR-gamma agonist activity thus making it a very interesting scaffold. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.067