1-(3-(trifluoromethyl)benzyl)-6-(4H-1,2,4-triazol-4-yl)-3,4-dihydroquinolin-2(1H)-one | 1564274-94-7

• 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: 1-(3-(trifluoromethyl)benzyl)-6-(4H-1,2,4-triazol-4-yl)-3,4-dihydroquinolin-2(1H)-one
• 英文别名: 6-(1,2,4-Triazol-4-yl)-1-[[3-(trifluoromethyl)phenyl]methyl]-3,4-dihydroquinolin-2-one；6-(1,2,4-triazol-4-yl)-1-[[3-(trifluoromethyl)phenyl]methyl]-3,4-dihydroquinolin-2-one
• CAS: 1564274-94-7
• 化学式: C₁₉H₁₅F₃N₄O
• 分子量: 372.35
• InChiKey: URTJMYYOQAHVCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  51
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4-二氢-2(1H)-喹啉酮 在 硫酸 、 palladium on activated charcoal 、 氢气 、 硝酸 、 sodium methylate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 14.0h， 生成 1-(3-(trifluoromethyl)benzyl)-6-(4H-1,2,4-triazol-4-yl)-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  Design, synthesis and evaluation of the antidepressant and anticonvulsant activities of triazole-containing quinolinones

  摘要：

  A series of 1-substituted-6-(4H-1,2,4-triazol-4-yl)-3,4-dihydroquinolin-2(1H)-ones were designed, synthesized, and screened for their antidepressant and anticonvulsant activities. Interestingly, compounds 5i, 5j, 5m, and 5n led to significant reductions in the immobility time in the forced swimming test at a dose of 50 mg/kg, and exhibited higher levels of efficacy than the reference standard fluoxetine. In addition, compound Si exhibited greater efficacy than fluoxetine in the tail suspension test. The results of an open field test further confirmed that compound 5i provided a good antidepressant effect. In the maximal electroshock seizure screen, compounds 5c and 5d showed moderate levels of anticonvulsant. activity and protected 100% of the animals at a dose of 100 mg/kg. None of the synthesized compounds showed any neurotoxicity in the rotarod test at a dose of 100 mg/kg. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.014

文献信息

• Design, synthesis and evaluation of the antidepressant and anticonvulsant activities of triazole-containing quinolinones
  作者：Xian-Qing Deng、Ming-Xia Song、Yan Zheng、Zhe-Shan Quan

  DOI：10.1016/j.ejmech.2013.12.014

  日期：2014.2

  A series of 1-substituted-6-(4H-1,2,4-triazol-4-yl)-3,4-dihydroquinolin-2(1H)-ones were designed, synthesized, and screened for their antidepressant and anticonvulsant activities. Interestingly, compounds 5i, 5j, 5m, and 5n led to significant reductions in the immobility time in the forced swimming test at a dose of 50 mg/kg, and exhibited higher levels of efficacy than the reference standard fluoxetine. In addition, compound Si exhibited greater efficacy than fluoxetine in the tail suspension test. The results of an open field test further confirmed that compound 5i provided a good antidepressant effect. In the maximal electroshock seizure screen, compounds 5c and 5d showed moderate levels of anticonvulsant. activity and protected 100% of the animals at a dose of 100 mg/kg. None of the synthesized compounds showed any neurotoxicity in the rotarod test at a dose of 100 mg/kg. (C) 2014 Elsevier Masson SAS. All rights reserved.