1,5-dimethyl-2-phenyl-4-[(3,4,5-trimethoxybenzylidene)amino]-1,2-dihydropyrazol-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,5-dimethyl-2-phenyl-4-[(3,4,5-trimethoxybenzylidene)amino]-1,2-dihydropyrazol-3-one
• 英文别名: 4-<(3,4,5-trimethoxybenzalidene)amino>antipyrine；4-{(3,4,5-trimethoxybenzylidine)amino}phenazone；DTAD；1,5-dimethyl-2-phenyl-4-{[(E)-(3,4,5-trimethoxyphenyl)methylidene]amino}-1,2-dihydro-3H-pyrazol-3-one；1,5-dimethyl-2-phenyl-4-[(3,4,5-trimethoxyphenyl)methylideneamino]pyrazol-3-one
• 化学式: C₂₁H₂₃N₃O₄
• mdl: MFCD01246747
• 分子量: 381.431
• InChiKey: DHPKWEDQAFHLJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  nickel(II) chloride hexahydrate 、 1,5-dimethyl-2-phenyl-4-[(3,4,5-trimethoxybenzylidene)amino]-1,2-dihydropyrazol-3-one 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  镍 (II) 和钴 (II) 配合物与氨基安替比林席夫碱配体的合成、光谱、DFT 和抗菌研究

  摘要：

  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

  DOI：

  10.1016/j.inoche.2024.112192
• 作为产物：
  描述：

  4-氨基安替比林 、 3,4,5-三甲氧基苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 1,5-dimethyl-2-phenyl-4-[(3,4,5-trimethoxybenzylidene)amino]-1,2-dihydropyrazol-3-one
  参考文献：
  名称：

  镍 (II) 和钴 (II) 配合物与氨基安替比林席夫碱配体的合成、光谱、DFT 和抗菌研究

  摘要：

  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

  DOI：

  10.1016/j.inoche.2024.112192

文献信息

• Microwave Assisted Synthesis, Spectrofluorometric Characterization of Azomethine as Intermediate for Transition Metal Complexes with Biological Application
  作者：Mohie E. M. Zayed、Abdullah M. Asiri、Salman A Khan

  DOI：10.1007/s10895-016-1782-7

  日期：2016.5

  to explore the analytical potential of azomethine dye. Azomethine go through the solubilization in different micelles and may be used as a probe or quencher to determine the critical micelle concentration (CMC) of SDS and CTAB. It’s coordinate to metal salt through the pyrazol-3-one oxygen and the azomethine nitrogen. The structure of ligand and its meal complexes was elucidated by IR, 1H, 13C-NMR, EI-MS

  偶氮甲碱（1，5-二甲基-2-苯基-[（3，4，5-三甲氧基亚苄基）氨基] -1，2-二氢吡唑-3-1）（DTAD）是通过4-氨基吩a与3，通过微波辐照得到4,5三甲苯氧基苯乙醛。为了研究偶氮甲胺染料的分析潜力，对诸如电子吸收，摩尔吸收率，振子强度，偶极矩，荧光量子产率的理化研究进行了研究。偶氮甲胺在不同的胶束中溶解，可以用作探针或淬灭剂以确定SDS和CTAB的临界胶束浓度（CMC）。它通过吡唑-3-酮氧和偶氮甲碱氮与金属盐配位。红外，1 H，13阐明了配体及其膳食配合物的结构C-NMR，EI-MS光谱方法和元素分析。这些化合物的抗菌活性首先通过椎间盘扩散试验在体外对两种革兰氏阳性细菌和两种革兰氏阴性细菌进行了测试，然后使用氯霉素作为参考药物对最低抑菌浓度进行了测试。结果表明，与氯霉素相比，化合物1.1是两种测试细菌的更好抑制剂。
• 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.
• Spectroscopic, electrochemical DNA binding and in vivo anti-inflammatory studies on newly synthesized Schiff bases of 4-aminophenazone
  作者：Nasima Arshad、Mukhtar Ahmad、Muhammad Zaman Ashraf、Humaira Nadeem

  DOI：10.1016/j.jphotobiol.2014.06.014

  日期：2014.9

  4-Aminophenazone (Ap-1) Schiff bases i.e., 4-(3,4,5-trimethoxybenzylidine) amino)phenazone (Ap-2), 4-(2-chlorobenzylidine) amino)phenazone (Ap-3) and 4-(4-chlorobenzylidine)amino} phenazone (Ap-4) were synthesized and characterized by different spectroscopic techniques. Interaction of these compounds with ds.DNA was investigated through UV-Visible spectroscopy, fluorescence spectroscopy and cyclic voltammetry at stomach (4.7) and blood (7.4) pH under 37 degrees C (human body temperature). Instrumental findings were further quantified both kinetically and thermodynamically. Results obtained through these techniques inferred intercalative mode of binding of all the compounds with DNA. The binding constant data, "K-b", and free energy change, Delta G, indicated comparatively greater binding affinity and more spontaneity of binding of compounds with DNA at stomach pH (4.7), respectively. However, among these compounds, Ap-4 showed comparatively greater binding at both the pH. Formation of compound-DNA complex was further confirmed through the decrease in diffusion rates after the addition of DNA. The in vivo anti-inflammatory activity of the compounds was evaluated using the carrageenan-induced hind paw edema method. The results revealed that among all the compounds, Ap-4 showed greater percentage of edema inhibition compared to standard drug. (C) 2014 Elsevier B.V. All rights reserved.
• Agarwal, R. K.; Arora, K., Polish Journal of Chemistry, 1993, vol. 67, # 2, p. 219 - 225
  作者：Agarwal, R. K.、Arora, K.

  DOI：——

  日期：——