4-((2,4-dihydroxybenzylidene)amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one | 58732-05-1

• 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-((2,4-dihydroxybenzylidene)amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
• 英文别名: 4-[(E)-[(2,4-Dihydroxyphenyl)methylidene]amino]-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one；4-[(2,4-dihydroxyphenyl)methylideneamino]-1,5-dimethyl-2-phenylpyrazol-3-one
• CAS: 58732-05-1
• 化学式: C₁₈H₁₇N₃O₃
• mdl: MFCD00382534
• 分子量: 323.351
• InChiKey: ZEQOCKGPOZWQGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  76.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  uranyl acetate dihydrate 、 4-((2,4-dihydroxybenzylidene)amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Characterization of Pd(II) and UO2(VI) complexes of some schiff base ligands

  摘要：

  DOI：

  10.1016/s0020-1693(00)83231-4
• 作为产物：
  描述：

  4-氨基安替比林 、 2,4-二羟基苯甲醛 在 magnetite(at)citric acid nanoparticles 作用下， 以 乙醇 为溶剂， 反应 0.28h， 以91%的产率得到4-((2,4-dihydroxybenzylidene)amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
  参考文献：
  名称：

  一种简单的生物相容性磁铁矿@柠檬酸的制备：一种高效的可重复使用的固体酸催化剂，用于快速合成安替比林席夫碱及其自由基清除潜力

  摘要：

  摘要 柠檬酸固定磁性纳米粒子（MNPs@CA）已被合成并用于制备生物重要的安替比林（1,5-二甲基-2-苯基-1,2-二氢-3H-吡唑-3-酮）衍生席夫碱 (3a-k) 在较短的反应时间内在超声处理下具有非常高的产率。通过FT-IR、粉末X射线衍射(XRD)、场发射扫描电子显微镜(FESEM)、高分辨透射电子显微镜(HRTEM)和热重分析(TGA)对催化剂进行表征。在后处理过程中使用外部磁铁很容易分离功能化的纳米粒子，并且表现出优异的可重复使用性，最多可重复使用 8 次，而催化活性没有任何显着损失。所有合成的化合物 (3a-k) 均通过 DPPH (2, 2-diphenyl-1-picrylhydrazyl) 方法对抗坏血酸的抗氧化活性进行了研究，其中一些得到了有希望的结果。图形概要

  DOI：

  10.1080/00397911.2018.1556795

文献信息

• Electrochemical studies of Schiff base compounds derived from antipyrine nucleus in ethanolic buffer solutions
  作者：Ibrahim S El-Hallag、Gad B El-Hefnawy、Youssef I Moharram、Enass M Ghoneim

  DOI：10.1139/v00-108

  日期：2000.9.1

  The electrochemical behaviour of Schiff base compounds derived from an antipyrine nucleus was investigated in 30% (v/v) ethanolic buffer solutions (pH 3-11) using various electrochemical techniques at mercury electrode. The results showed that, the total limiting current of each of the studied compounds corresponds to 2-electron transfer process. The mechanistic pathway of the electrode reaction of the investigated compounds at mercury electrode, the effect of the medium, and the evaluation of the electrode reaction parameters were illustrated and discussed.Key words: Schiff base, antipyrine nucleus, electrode reaction, electrochemical parameters, cyclic voltammetry.

  对来自苯巯基核的Schiff碱化合物的电化学行为在30%（体积分数）乙醇缓冲溶液（pH 3-11）中使用各种电化学技术在汞电极上进行了研究。结果表明，所研究化合物的总极限电流对应于2电子转移过程。在汞电极上研究化合物的电极反应的机理途径，介质的影响以及电极反应参数的评估进行了说明和讨论。关键词：Schiff碱，苯巯基核，电极反应，电化学参数，循环伏安法。
• Synthesis, characterization, electrochemical studies and antimicrobial activities of metal complexes
  作者：A. Z. El-Sonbati、M. A. Diab、M. I. Abou-Dobara、A. M. Eldesoky、H. R. Issa

  DOI：10.1007/s13738-021-02354-1

  日期：2022.3

  that the metal complexes had more potent antimicrobial than the parent Schiff base ligand against one or more microbial species. Some complexes showed higher activity than ligand. The complex (3) has antibacterial activities against Bacillus cereus, Klebsiella pneumoniae and Staphylococcus aureus. The antibacterial activity of complex (3) was the highest ones than the ligand and other complexes as well

  由缩合得到的席夫碱 4-[(2, 4-dihydroxy-benzylidene)-amino]-1, 5-dimethyl-2-phenyl-1, 2-dihydroxo-pyrazol-3-one (H 2 L) 的金属配合物合成了 2,4-二羟基苯甲醛和 4-氨基安替比林，并通过 FT-IR 光谱、元素分析、1 H 和13 C NMR、质谱、紫外-可见光、X 射线衍射、摩尔电导、磁矩和热分析对其进行了表征(TGA)。元素分析证明，配合物通式为[M(HL)(X)(OH 2 )] 2，其中M=Cu(II)；X = OAc - (1) ; NO 3 - (2) ; Cl - (3) , M = Co(II) (4), Mn(II) (5) ; X = OAc 和 [UO 2 (HL)] 2 .2(OAc)} (6)。根据FT-IR光谱数据，发现H 2 L配体与偶氮甲碱基的氮原子、酚基的氧
• Polymer complexes: LXXX—characterization, DNA cleavage properties, antimicrobial activity and molecular docking studies of transition metal complexes of Schiff base
  作者：M. A. Diab、A. K. El-Sayed、M. I. Abou-Dobara、H. R. Issa、A. Z. El-Sonbati

  DOI：10.1007/s13738-023-02755-4

  日期：——

  complexes of Cu(II), Co(II), Ni(II), Mn(II) and Cd(II) with 4-[(2,4-dihydroxy-benzylidene)-amino]-1,5-dimethyl-2-phenyl-1,2-dihydroxo-pyrazol-3-one (H2L) ligand were prepared and characterized. From the elemental analysis data, the polymer complexes were proposed to have the general formula [M(L)(OH2)2]·xH2O}n where M = Cu(II)(1), x = 1.25; M = Co(II)(2), Ni(II)(3), Mn(II)(4) and Cd(II)(5), x = nil. The

  Cu(II)、Co(II)、Ni(II)、Mn(II) 和 Cd(II) 与 4-[(2,4-dihydroxy-benzylidene)-amino]-1 的一系列新聚合物络合物，制备并表征了5-二甲基-2-苯基-1,2-二羟基-吡唑-3-酮 (H 2 L) 配体。根据元素分析数据，提出聚合物配合物具有通式[M(L)(OH 2 ) 2 ]· x H 2 O} n其中M = Cu(II)( 1 ), x  = 1.25；M = Co(II)( 2 ), Ni(II)( 3 ), Mn(II)( 4 ) 和 Cd(II)( 5 ), x = 无。摩尔电导数据显示所有聚合物络合物都是非电解质。合成的配体与其金属聚合物配合物相比，筛选了它们对细菌物种的抗菌活性。发现金属配合物比席夫碱配体对某些微生物物种具有更强的抗菌活性。一些复合物显示出比配体更高的活性。Cd(II)络合物(5)对蜡样芽孢杆菌
• 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.
• Antipyrine based Schiff’s base as a reversible fluorescence turn “off-on-off” chemosensor for sequential recognition of Al3+ and F− ions: A theoretical and experimental perspective
  作者：Priya Yadav、Mitlesh Kumari、Yachana Jain、Madhu Agarwal、Ragini Gupta

  DOI：10.1016/j.saa.2019.117596

  日期：2020.2

  A Schiffs base probe (L) based on antipyrine has been intended, synthesized and assessed as a turn "off-on-off" probe for successive recognition of Al3+ and F-. The probe L act out as a turn "on" fluorescence probe towards Al3+ in methanol at pH 6 which turned "off" by F- at 433 nm. The 1:1 binding stoichiometry of L + Al3+ complex was revealed by Job's plot and approved by ESI-HRMS data. The binding constant and limit of detection of probe L for Al3+ were found to be 2.951 x 10(7) M-1 and 0.61 x 10(-7) M respectively, which is lesser than the acceptable limit (0.74 x 10(-7) M) in drinking water. The proposed binding sites and the mode of interaction of probe L was studied and validated by H-1 NMR titration and Al-27 NMR spectroscopic studies. To get detailed vision into binding mechanism and optimized structure of receptor L and L + Al3+, L+ Al3+ + F- complex, theoretical calculations using DFT/DND and TDDFT method were performed. Furthermore, probe L can mimic INHIBIT logic function using Al3+ and F- being logic inputs and examining the fluorescence maxima at 433 nm as output. (C) 2019 Elsevier B.V. All rights reserved.