4-[2-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-ylimino-methyl)benzylideneamino]-1,2-dihydro-1,5-dimethyl-2-phenylpyrazol-3-one | 326006-96-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[2-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-ylimino-methyl)benzylideneamino]-1,2-dihydro-1,5-dimethyl-2-phenylpyrazol-3-one
• 英文别名: 4-((E)-{2-[N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)carboximidoyl]benzylidene}amino)-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one；4-[[2-[(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)iminomethyl]phenyl]methylideneamino]-1,5-dimethyl-2-phenylpyrazol-3-one
• CAS: 326006-96-6
• 化学式: C₃₀H₂₈N₆O₂
• 分子量: 504.591
• InChiKey: NMISZLRPUKPURP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-氨基安替比林 、 邻苯二甲醛 以 乙醇 为溶剂， 反应 6.0h， 以42%的产率得到2-[(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-ylimino)methyl]benzaldehyde
  参考文献：
  名称：

  Synthesis of novel Schiff base analogues of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one and their evaluation for antioxidant and anti-inflammatory activity

  摘要：

  4-Aminoantipyrine (4-amino-1,5-dimethyl-2-phenylpyrazole-3-one) and its analogues have been found to be compounds of interest for their anti-inflammatory, analgesic, antiviral, antipyretic, antirheumatic and antimicrobial activities. In the present study, Schiff base analogues of 4-aminoantipyrine were synthesized by the condensation reaction with substituted benzaldehydes and then evaluated for their antioxidant and anti-inflammatory activities. From among the synthesized compounds (3a-m, 4 and 5), 3k and 3f exhibited the highest antioxidant activity followed by 3g, 3l, 3c, 3i, 5,3mand 3h. The IC50 values for compounds 3k and 3f were found to be 0.44 and 0.93 mu M, respectively, comparable to that of ascorbic acid (IC50 0.41 mu M), a standard antioxidant agent. From the comparisons between the hydroxylated and methoxylated compounds, the rank order of antioxidant activity for the products resulting from benzylidene phenyl ring substitution was 2,4,6-OH > 3,4-OH > 3-OMe-4-OH > 3,5-OMe-4-OH > 2,4-OH > 3-Me-4-OMe > 3,4-OMe > 4-OMe > 4-OH. The structure-activity relationship study revealed that the position and nature of the substituted group on the benzylidene phenyl ring of the Schiff base analogues of 4-aminoantipyrine play an important role in their antioxidant activity. The anti-inflammatory activity of 3f, which also exhibited excellent antioxidant activity, was evaluated in terms of its inhibition of NO production, an inflammatory modulator, in LPS pretreated RAW 264.7 cells using the Griess method. We also examined whether or not this compound had effect on iNOS and COX-2 mRNA expression in RAW 264.7 cells. It was observed that compound 3f significantly reduced NO production and inhibited LPS-stimulated iNOS and COX-2 mRNA levels in a dose-dependent manner. Overall, 3f showed promising antioxidant and anti-inflammatory activities and may be used as the lead compound in a future study. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.058

文献信息

• Synthesis of novel Schiff base analogues of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one and their evaluation for antioxidant and anti-inflammatory activity
  作者：Mohammad Sayed Alam、Jung-Hyun Choi、Dong-Ung Lee

  DOI：10.1016/j.bmc.2012.04.058

  日期：2012.7

  4-Aminoantipyrine (4-amino-1,5-dimethyl-2-phenylpyrazole-3-one) and its analogues have been found to be compounds of interest for their anti-inflammatory, analgesic, antiviral, antipyretic, antirheumatic and antimicrobial activities. In the present study, Schiff base analogues of 4-aminoantipyrine were synthesized by the condensation reaction with substituted benzaldehydes and then evaluated for their antioxidant and anti-inflammatory activities. From among the synthesized compounds (3a-m, 4 and 5), 3k and 3f exhibited the highest antioxidant activity followed by 3g, 3l, 3c, 3i, 5,3mand 3h. The IC50 values for compounds 3k and 3f were found to be 0.44 and 0.93 mu M, respectively, comparable to that of ascorbic acid (IC50 0.41 mu M), a standard antioxidant agent. From the comparisons between the hydroxylated and methoxylated compounds, the rank order of antioxidant activity for the products resulting from benzylidene phenyl ring substitution was 2,4,6-OH > 3,4-OH > 3-OMe-4-OH > 3,5-OMe-4-OH > 2,4-OH > 3-Me-4-OMe > 3,4-OMe > 4-OMe > 4-OH. The structure-activity relationship study revealed that the position and nature of the substituted group on the benzylidene phenyl ring of the Schiff base analogues of 4-aminoantipyrine play an important role in their antioxidant activity. The anti-inflammatory activity of 3f, which also exhibited excellent antioxidant activity, was evaluated in terms of its inhibition of NO production, an inflammatory modulator, in LPS pretreated RAW 264.7 cells using the Griess method. We also examined whether or not this compound had effect on iNOS and COX-2 mRNA expression in RAW 264.7 cells. It was observed that compound 3f significantly reduced NO production and inhibited LPS-stimulated iNOS and COX-2 mRNA levels in a dose-dependent manner. Overall, 3f showed promising antioxidant and anti-inflammatory activities and may be used as the lead compound in a future study. (C) 2012 Elsevier Ltd. All rights reserved.