4-oxo-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxylic acid | 1449221-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-oxo-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 6-(2-methylphenyl)-4-oxo-1H-quinoline-3-carboxylic acid
• CAS: 1449221-76-4
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: HCPKDCSOBFIHKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-oxo-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxylic acid 、 3-溴苄胺 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.25h， 以57.05%的产率得到N-(3-bromobenzyl)-4-oxo-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  4-Oxo-1,4-dihydro-quinoline-3-carboxamides as BACE-1 inhibitors: Synthesis, biological evaluation and docking studies

  摘要：

  In this work, we report a series of new 4-oxo-1,4-dihydro-quinoline-3-carboxamide derivatives as,beta-secretase (BACE-1) inhibitors. Supported by docking study, a small library of derivatives were designed, synthesized and biologically evaluated in vitro. The studies revealed that the most potent analog 14e (IC50 = 1.89 mu M) with low cellular cytotoxicity and high predicted blood brain barrier permeability, could serve as a good structure for further modification.(c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.025
• 作为产物：
  描述：

  (4-溴苯胺亚甲基)丙二酸二乙酯 在 四(三苯基膦)钯 、 potassium carbonate 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 26.0h， 生成 4-oxo-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  4-Oxo-1,4-dihydro-quinoline-3-carboxamides as BACE-1 inhibitors: Synthesis, biological evaluation and docking studies

  摘要：

  In this work, we report a series of new 4-oxo-1,4-dihydro-quinoline-3-carboxamide derivatives as,beta-secretase (BACE-1) inhibitors. Supported by docking study, a small library of derivatives were designed, synthesized and biologically evaluated in vitro. The studies revealed that the most potent analog 14e (IC50 = 1.89 mu M) with low cellular cytotoxicity and high predicted blood brain barrier permeability, could serve as a good structure for further modification.(c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.025