2-[[2-(3-Methyl-4-oxophthalazin-1-yl)acetyl]amino]-4-phenyl-1,3-thiazole-5-carboxylic acid | 1458056-13-7

• 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: 2-[[2-(3-Methyl-4-oxophthalazin-1-yl)acetyl]amino]-4-phenyl-1,3-thiazole-5-carboxylic acid
• 英文别名: 2-[[2-(3-methyl-4-oxophthalazin-1-yl)acetyl]amino]-4-phenyl-1,3-thiazole-5-carboxylic acid
• CAS: 1458056-13-7
• 化学式: C₂₁H₁₆N₄O₄S
• 分子量: 420.448
• InChiKey: SQHKYCYJBMTPCU-UHFFFAOYSA-N

物化性质

• 密度：
  1.48±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (4-氧代-3,4-二氢二氮杂萘-1-基)-乙酸乙酯 在 potassium tert-butylate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.83h， 生成 2-[[2-(3-Methyl-4-oxophthalazin-1-yl)acetyl]amino]-4-phenyl-1,3-thiazole-5-carboxylic acid
  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