4-(3,4-二甲氧基苄亚基氨基)安替比林 | 78439-83-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(3,4-二甲氧基苄亚基氨基)安替比林
• 英文名称: 4-(3,4-dimethoxybenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
• 英文别名: 4-[3,4-dimethoxybenzylidene]-1,5-dimethyl-2-phenyl-1,2-dihydropyrazole-3-one；4-(3',4'-dimethoxybenzaldehydene)-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one；4-(3',4'-dimethoxybenzaldehydene)2-3-dimethyl-1-phenyl-3-pyrazolin-5-one；4-(3',4'-dimethoxybenzylidene)-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one；N⁴-(3,4-dimethoxybenzylidene)aminoantipyrine；N**4-(3,4-dimethoxy-benzylidene)aminoantipyrine；4-{[(E)-(3,4-dimethoxyphenyl)methylidene]amino}-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one；4-[(3,4-dimethoxyphenyl)methylideneamino]-1,5-dimethyl-2-phenylpyrazol-3-one
• CAS: 78439-83-5
• 化学式: C₂₀H₂₁N₃O₃
• mdl: MFCD00808361
• 分子量: 351.405
• InChiKey: CLWGXFVQBMLUHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对羟基苯乙胺 、 4-(3,4-二甲氧基苄亚基氨基)安替比林 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以79%的产率得到3-4-dimethoxybenzylidene-4-aminoantipyrinyl-4-aminoethyl-phenol
  参考文献：
  名称：

  一种新型的生物活性酪胺衍生的席夫碱及其过渡金属配合物作为选择性DNA结合剂

  摘要：

  一种新型的酪胺衍生的席夫碱3-4-二甲氧基亚苄基-4-氨基抗吡啶基-4-氨基乙基苯酚（L）及其一系列过渡金属配合物，类型为ML 2 Cl 2其中M = Cu（II），Ni（ II），Co（II）和Zn（II）的设计和合成。它们的结构特征和其他特性是从元素分析，磁化率和摩尔电导率以及质量，IR，UV-vis，1推导出来的1 H NMR和EPR光谱研究。使用电子吸收光谱，粘度测量，循环伏安法和分子对接分析研究了这些复合物与小牛胸腺DNA（CT-DNA）的结合特性。结果表明，金属（II）配合物通过较小的凹槽结合与DNA相互作用。还通过凝胶电泳研究了相互作用。有趣的是，发现在AH 2（抗坏血酸）存在下，所有复合物均能有效切割环状质粒pUC19超卷曲（SC）DNA 。与游离配体相比，该复合物显示出增强的抗真菌和抗菌活性。

  DOI：

  10.1016/j.saa.2010.12.056
• 作为产物：
  描述：

  4-氨基安替比林 、 3,4-二甲氧基苯甲醛 以 乙醇 为溶剂， 反应 3.0h， 以89%的产率得到4-(3,4-二甲氧基苄亚基氨基)安替比林
  参考文献：
  名称：

  吡唑酮和基于氨基脲/硫代氨基脲的衍生物的三配位席夫碱配体的单核Cu（II）和Zn（II）金属配合物的光谱，磁性，杀菌筛选，DNA结合和光解研究

  摘要：

  我们描述了4-（3'，4'-dimethoxybenzaldehydene）2-3-dimethyl-1-phenyl-3-pyrazolin-5-semicarbazone（1a）的铜（II）和锌（II）配位化合物的合成和表征，4-（3'，4'-二甲氧基苯甲醛）2-3-二甲基-1-苯基-3-吡唑啉-5-硫代半脲（1b），4-（3'-羟基-4'-硝基苯甲醛）2-3-二甲基基-1-苯基-3-吡唑啉-5-半卡巴zone （1c）和4-（3'-羟基-4'-硝基苯甲酰二氢）2-3-二甲基-1-苯基-3-吡唑啉-5-硫代半卡巴carb（1d）。所有的远端化合物的一般组成为[ML 2 ]（M = Cu（II）和Zn（II））；L =希夫碱（1a – 1d）。所有复合物的特征在于元素分析，摩尔电导率，IR，1 H NMR，UV-vis，ESI-Mass，磁化率测量，循环伏安测量和EPR光谱研究。已经发现

  DOI：

  10.1016/j.saa.2010.03.007

文献信息

• DNA interaction, enhanced DNA photocleavage, electrochemistry, thermal investigation and biopotencial properties of new mixed-ligand complexes of Cu(II)/VO(IV) based on Schiff bases
  作者：Natarajan Raman、Abraham Selvan

  DOI：10.1016/j.molstruc.2010.10.038

  日期：2011.1

  Abstract Using the Schiff base ligand, dbdppo (4-(3′,4′-dimethoxybenzaldehydene)2-3-dimethyl-1-phenyl-3-pyrazolin-5-one or hnbdppo (4-(3′-hydroxy-4′-nitrobenzaldehydene)2-3-dimethyl-1-phenyl-3-pyrazolin-5-one with polypyridyl ligand(s) as co-ligand(s), Cu(II) and VO(IV) complexes have been synthesized and characterized by the physicochemical properties. The electrochemical properties, DNA binding affinities

  光谱研究与循环伏安法和粘度实验一起支持这两种复合物通过部分嵌入 DNA 的碱基对与 CT DNA 结合。此外，已发现这些复合物在 365 nm 辐射下促进质粒 DNA pBR322 的光裂解。此外，与它们的金属配合物相比，合成的配体筛选了它们对细菌和真菌物种的抗微生物活性。活性数据表明金属配合物比母体希夫碱配体具有更强的抗微生物效力。已发现这些复合物在 365 nm 辐射下促进质粒 DNA pBR322 的光裂解。此外，与它们的金属配合物相比，合成的配体筛选了它们对细菌和真菌物种的抗微生物活性。活性数据表明金属配合物比母体席夫碱配体具有更强的抗微生物效力。已发现这些复合物在 365 nm 辐射下促进质粒 DNA pBR322 的光裂解。此外，与它们的金属配合物相比，合成的配体筛选了它们对细菌和真菌物种的抗微生物活性。活性数据表明金属配合物比母体席夫碱配体具有更强的抗微生物效力。
• Synthesis, DNA binding, and antimicrobial studies of novel metal complexes containing a pyrazolone derivative Schiff base
  作者：Natarajan Raman、Ramaraj Jeyamurugan、Mariyyappan Subbulakshmi、Raja Boominathan、Chithu Yuvarajan

  DOI：10.2478/s11696-010-0003-0

  日期：2010.1.1

  caused by the change of coordination geometry by the vanadyl ion resulting in a somewhat unfavorable configuration for the DNA binding. Oxidative DNA cleavage activities of the complexes were studied with supercoiled (SC) pUC19 DNA using gel electrophoresis; the mechanism studies revealed that the hydroxyl radical is likely to be the reactive species responsible for the cleavage of pUC19 DNA by the synthesized

  从4-[（3,4-二甲氧基亚苄基）氨基衍生的席夫碱合成了一系列新颖的Co（II），Ni（II），Cu（II），Zn（II）和VO（IV）配合物。 ] -1,5-二甲基-2-苯基-1，2-二氢吡唑-3-一和1,2-二氨基苯。通过分析和光谱技术确定结构特征。通过光谱方法和粘度测量研究了合成的复合物与小牛胸腺DNA（CT DNA）的结合。实验结果表明，该复合物能够与DNA形成加合物，并能够通过改变碱基堆积来扭曲双螺旋结构。VO（IV）配合物的较低DNA亲和力是由于钒基离子配位几何形状的变化而导致，导致DNA结合的构型有些不利。使用凝胶电泳，用超螺旋（SC）pUC19 DNA研究了复合物的氧化DNA切割活性。机理研究表明，羟基自由基很可能是合成复合物裂解pUC19 DNA的反应性物种。通过圆盘扩散法监测所研究化合物的体外抗菌筛选作用。合成的席夫碱复合物表现出比各自的游离席夫碱更高的抗菌活性。
• Synthesis, spectral, DFT, and antibacterial studies of Nickel(II) and Cobalt(II) complexes with aminoantipyrine based Schiff base ligands
  作者：Har Lal Singh、Preeti Kulhari、Garima Choudhary、Sarita Khaturia

  DOI：10.1016/j.inoche.2024.112192

  日期：2024.4

  investigated, despite their widespread use as medicines and bioactive compounds. In this study, we present the synthesis of new Ni(II) and Co(II) Schiff base complexes [M(L)Cl] using the following ligands: 1,5-dimethyl-2-phenyl-4-((3,4,5-trimethoxy-benzylidene)amino)-1H-pyrazol-3(2H)-one (L), 4-((4-methoxybenzylidene)amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (L), 4-((3,4-dimethoxy-benzyli-dene)amino)-1

  席夫碱配合物是一类分子，由于其有趣的化学和物理性质以及在各个科学领域的多样化适用性而引起了极大的关注。尽管希夫碱和氨基安替比林衍生物广泛用作药物和生物活性化合物，但它们仍在不断地被研究。在这项研究中，我们使用以下配体合成了新型 Ni(II) 和 Co(II) 席夫碱配合物 [M(L)Cl]：1,5-二甲基-2-苯基-4-((3, 4,5-三甲氧基亚苄基)氨基)-1H-吡唑-3(2H)-酮(L),4-((4-甲氧基亚苄基)氨基)-1,5-二甲基-2-苯基-1H-吡唑- 3(2H)-一(L), 4-((3,4-二甲氧基-亚苄基)氨基)-1,5-二甲基-2-苯基-1H-吡唑-3(2H)-一(L) , 4-((1-([1,1'-联苯基]-4-基)亚乙基)氨基)-1,5-二甲基-2-苯基-1H-吡唑-3(2H)-酮(L ), 4-((4-羟基-3-甲氧基-亚苄基)氨基)-1,5-二甲基-2-苯基-1
• 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.
• Design, synthesis, antimicrobial, anticancer evaluation, and QSAR studies of 4-(substituted benzylidene-amino)-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-ones
  作者：Sumit Sigroha、Balasubramanian Narasimhan、Pradeep Kumar、Anurag Khatkar、Kalavathy Ramasamy、Vasudevan Mani、Rakesh Kumar Mishra、Abu Bakar Abdul Majeed

  DOI：10.1007/s00044-011-9906-8

  日期：2012.11

  A series of 4-(substituted benzylidene-amino)-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-ones (1-17) was synthesized and tested in vitro for its antimicrobial and anticancer potentials. The biological screening results indicated that compounds having m-chloro substituent on benzaldehyde portion showed antimicrobial potential, whereas compounds having chloro, methoxy, and hydroxyl groups showed anticancer potential. The quantitative structure activity relationship (QSAR) studies indicated the importance of topological parameter, valence first order molecular connectivity index in describing antifungal activity. The developed QSAR models, however, were statistically insignificant with reference to anticancer activity of the synthesized compounds.