(E)-4-[4-isopropylbenzylideneamino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-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: (E)-4-[4-isopropylbenzylideneamino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
• 化学式: C₂₁H₂₃N₃O
• 分子量: 333.433
• InChiKey: VBEGJFKKGYNONM-HYARGMPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  39.29
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  potassium tetrachloroplatinate(II) 、 (E)-4-[4-isopropylbenzylideneamino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 8.0h， 以60%的产率得到[Pt((E)-4-[4-isopropylbenzylideneamino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one)Cl₂]
  参考文献：
  名称：

  Synthesis, characterization, and biological evaluation of Schiff base–platinum(II) complexes

  摘要：

  The platinum complexes of Schiff base ligands derived from 4-aminoantipyrine and a few substituted aldehydes were synthesized and characterized by elemental analysis, mass, H-1 NMR, IR, electronic spectra, molar conductance, and powder XRD. The structure of one of the ligands L-5 was confirmed by a single crystal XRD, analysis. The Schiff base ligand crystallized in the triclinic, space group P-1 with a = 7.032(2) angstrom, b = 9.479(3) angstrom, c = 12.425(4) angstrom, alpha = 101.636(3)degrees, beta = 99.633(3)degrees, gamma = 94.040(3)degrees, V= 795.0(4) angstrom(3), Z= 2, F(000) = 352, D-c= 1.405 mg/m(3), mu = 0.099 mm(-1), R= 0.0378, and wR = 0.0967. The spectral results show that the Schiff base ligand acts as a bidentate donor coordinating through the azomethine nitrogen and the carbonyl oxygen atoms. The geometrical structures of these complexes are found to be square planar. Antimicrobial studies indicate that these complexes exhibit better activity than the ligand. The anticancer activities of the complexes have also been studied towards human cervical cancer cell line (HeLa), Colon Cancer Cells (HCT116) and Epidermoid Carcinoma Cells (A431) and it was found that the [Pt(L-3)Cl-2] complex is more active. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2015.02.030
• 作为产物：
  描述：

  4-氨基安替比林 、 4-异丙基苯甲醛 以 甲醇 为溶剂， 反应 5.0h， 以65%的产率得到(E)-4-[4-isopropylbenzylideneamino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
  参考文献：
  名称：

  Synthesis, characterization, and biological evaluation of Schiff base–platinum(II) complexes

  摘要：

  The platinum complexes of Schiff base ligands derived from 4-aminoantipyrine and a few substituted aldehydes were synthesized and characterized by elemental analysis, mass, H-1 NMR, IR, electronic spectra, molar conductance, and powder XRD. The structure of one of the ligands L-5 was confirmed by a single crystal XRD, analysis. The Schiff base ligand crystallized in the triclinic, space group P-1 with a = 7.032(2) angstrom, b = 9.479(3) angstrom, c = 12.425(4) angstrom, alpha = 101.636(3)degrees, beta = 99.633(3)degrees, gamma = 94.040(3)degrees, V= 795.0(4) angstrom(3), Z= 2, F(000) = 352, D-c= 1.405 mg/m(3), mu = 0.099 mm(-1), R= 0.0378, and wR = 0.0967. The spectral results show that the Schiff base ligand acts as a bidentate donor coordinating through the azomethine nitrogen and the carbonyl oxygen atoms. The geometrical structures of these complexes are found to be square planar. Antimicrobial studies indicate that these complexes exhibit better activity than the ligand. The anticancer activities of the complexes have also been studied towards human cervical cancer cell line (HeLa), Colon Cancer Cells (HCT116) and Epidermoid Carcinoma Cells (A431) and it was found that the [Pt(L-3)Cl-2] complex is more active. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2015.02.030

文献信息

• Novel antipyrine substituted 4-thiazolidinones: Synthesis, DNA binding and topoisomerase inhibition activities, and in-silico studies
  作者：Emine Bagdatli、Seda Mesci、Tuba Yildirim

  DOI：10.1016/j.molstruc.2024.139192

  日期：2024.12

  specificity and capacity of the compounds to catalytically generate topoisomerase I activity were also examined using agarose gel electrophoresis. The compounds induced changes in DNA mobility and showed a topoisomerase I inhibitory effect at all doses. 4-Thiazolidinones had a higher affinity in DNA and topoisomerase I than the Schiff bases. DNA binding and topoisomerase I activities were most effective at low

  在这项研究中，我们报道了含有来源于 Schiff 碱起始化合物 （2a-e） 的安替比林 （3a-e） 的新型 4-噻唑烷酮的合成和表征。希夫碱是使用天然来源的醛合成的，例如香茅醛、小茴香醛、2-噻唑甲醛、5-甲基糠醛和丁香醛。他们的 FTIR 光谱揭示了化合物 3b 和 3d 的烯醇互变异构固态结构。还使用琼脂糖凝胶电泳检查了 pUC18 质粒 DNA 结合特异性和化合物催化产生拓扑异构酶 I 活性的能力。这些化合物诱导 DNA 迁移率的变化，并在所有剂量下显示出拓扑异构酶 I 抑制作用。4-噻唑烷酮在 DNA 和拓扑异构酶 I 中的亲和力高于 Schiff 碱基。DNA 结合和拓扑异构酶 I 活性在低浓度 （6 μM） 时对希夫碱基 2a、d 和 4-噻唑烷酮 3a、d 的化合物最有效。此外，本研究还提出了解决分子类似药物特性的计算方法。在计算机模拟研究中，2a、d 和 3a、d 化合