2-(4-oxo-3-(2-oxo-2-phenylethyl)-3, 4-dihydrophthalazin-1-yl) acetic acid | 1458056-23-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-oxo-3-(2-oxo-2-phenylethyl)-3, 4-dihydrophthalazin-1-yl) acetic acid
• 英文别名: 2-(4-Oxo-3-phenacylphthalazin-1-yl)acetic acid；2-(4-oxo-3-phenacylphthalazin-1-yl)acetic acid
• CAS: 1458056-23-9
• 化学式: C₁₈H₁₄N₂O₄
• 分子量: 322.32
• InChiKey: IKGSSDJOTDGPPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  87
• 氢给体数：
  1
• 氢受体数：
  5

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 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 2-(4-oxo-3-(2-oxo-2-phenylethyl)-3, 4-dihydrophthalazin-1-yl) acetic 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

文献信息

• Discovery of thiazolyl-phthalazinone acetamides as potent glucose uptake activators via high-throughput screening
  作者：Madhavi Agrawal、Prashant Kharkar、Sonali Moghe、Tushar Mahajan、Vaishali Deka、Chandni Thakkar、Amrutha Nair、Chirag Mehta、Julie Bose、Asha Kulkarni-Almeida、Dilip Bhedi、Ram A. Vishwakarma

  DOI：10.1016/j.bmcl.2013.07.067

  日期：2013.10

  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.