1,5-dimethyl-2-phenyl-4-[4-(propan-2-yl)benzylidene]amino-1,2-dihydro-3H-pyrazol-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-[4-(propan-2-yl)benzylidene]amino-1,2-dihydro-3H-pyrazol-3-one
• 英文别名: 4-{[(E)-(4-isopropylphenyl)methylidene]amino}-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one；1,5-dimethyl-2-phenyl-4-[(4-propan-2-ylphenyl)methylideneamino]pyrazol-3-one
• 化学式: C₂₁H₂₃N₃O
• mdl: MFCD00030513
• 分子量: 333.433
• InChiKey: VBEGJFKKGYNONM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 1,5-dimethyl-2-phenyl-4-[4-(propan-2-yl)benzylidene]amino-1,2-dihydro-3H-pyrazol-3-one 以 甲苯 为溶剂， 反应 4.0h， 以31%的产率得到fac-[Re(CO)₃(4-aminoantipyrene)Cl]
  参考文献：
  名称：

  Coordination susceptibilities of cinnamaldehyde and cuminaldehyde derived Schiff bases towards the fac-[Re(CO)3]+ core: Formation, computational and DNA interaction studies

  摘要：

  Herein, we explore the coordination behaviours of Schiff bases derived from constituents of essential oils (viz. cinnamaldehyde and cuminaldehyde) and aromatic amines (viz 2-aminophenol and 4-aminoantipyrene) towards the facial tricarbonylrhenium(I) core. The resultant rhenium(I) compounds: (mu-X)(2)[Re(CO)(3)](2) {where X = 2{[3-Phenylprop-2-en-1-ylidene]amino}phenol (ciap) (for 1) or 2-{[4-(propan-2-yl)benzylidene]amino}phenol (cuap) (for 2), fac-[Re(CO)(3)(apy)Cl] (apy = 4-aminoantipyrene) (3) and fac-[Re(CO)(3)(cinap)Cl] (cinap = 1,5-dimethyl-2-phenyl-4-{[3-phenylprop-2-en-1-ylidene]amino}-1,2-dihydro-3H-pyrazol-3-one) (4) were formed. The metal compounds were spectroscopically characterized and structural elucidations were confirmed by single crystal X-ray diffraction. DFT studies were utilized to rationalize the contrasting coordination behaviours of the structural analogues, 1,5-dimethyl-2-phenyl-4-{[4-(propan-2-yl)benzylidene]amino}-1,2-dihydro-3H-pyrazol-3-one (cumap) and cinap in the formation of 3 and 4, respectively. These metal compounds showed affinities towards Calf-Thymus DNA based on UV-Vis DNA binding titrations and molecular docking studies revealed that they are groove binders. In addition, gel electrophoresis experiments indicated that steric factors has an influence on the DNA cleavage activities of the mono- and dinuclear rhenium(I) compounds. (C) 2018 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2018.03.032
• 作为产物：
  描述：

  4-氨基安替比林 、 4-异丙基苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以86%的产率得到1,5-dimethyl-2-phenyl-4-[4-(propan-2-yl)benzylidene]amino-1,2-dihydro-3H-pyrazol-3-one
  参考文献：
  名称：

  新型苯甲醛衍生物的制备及其生物活性

  摘要：

  （2021年）。新型孜然醛衍生物的制备及其生物活性。国际有机制剂和程序：Vol。53，第3号，第240-253页。

  DOI：

  10.1080/00304948.2020.1871574

文献信息

• Stabilization of the ruthenium (II) and -(III) centres by chelating N-donor ligands: Synthesis, characterization, biomolecular affinities and computational studies
  作者：Sanam Maikoo、Irvin Noel Booysen、Bheki Xulu、Lydia Rhyman、Ponnadurai Ramasami

  DOI：10.1016/j.molstruc.2021.130986

  日期：2021.11

  were conducted primarily by spectroscopic techniques while the single crystal X-ray analysis revealed the distorted octahedrons of the respective metal compounds. Voltammetry experiments of 1–3 illustrated one-electron quasi-reversible redox waves which are attributed to metal oxidation state interconversions. CT-DNA binding affinities and modes of the novel metal complexes 1–3 as well as the formerly

  钌席夫碱金属配合物的抗癌活性与其空间因子和理化性质密切相关。我们研究的核心目标是合成和表征源自肉桂醛、孜然醛或 4-氨基安替比林的新型钌席夫碱化合物。此外，上述金属化合物和两种先前报道的钌席夫碱化合物的立体电子特征与其抗氧化和生物分子相互作用能力有关。因此，我们证明了具有螯合 N-供体配体的新型单核钌 (III) 化合物的形成：fac -[RuCl 3 (PPh 3 )(ap)] ( 1 ) (ap = 4-氨基安替比林)，反式-P-[Ru(PPh 3 ) 2 (cinap) 2 ](PF 6 ) ( 2 ) (cinap = 1,5-二甲基-2-苯基-4-[3-苯基丙-2-en-1-亚基]氨基} -1,2-二氢-3- ħ吡唑-3-酮）和顺式-氯，反式- P-将[RuCl 2（PPH 3）2（cumbh）]（3）（cumbh =  N” - (4-异丙基亚苄基)苯甲酰肼)。结构确认主要通过光谱技术进行，而单晶
• Formation, biomolecular interaction and cytotoxicity studies of new organoruthenium Schiff base compounds
  作者：Sanam Maikoo、Candace Davison、Jo-Anne de la Mare、Irvin Noel Booysen

  DOI：10.1016/j.poly.2023.116640

  日期：2023.11
• Coordination susceptibilities of cinnamaldehyde and cuminaldehyde derived Schiff bases towards the fac-[Re(CO)3]+ core: Formation, computational and DNA interaction studies
  作者：Muhammed Bilaal Ismail、Irvin Noel Booysen、Matthew Piers Akerman

  DOI：10.1016/j.ica.2018.03.032

  日期：2018.5

  Herein, we explore the coordination behaviours of Schiff bases derived from constituents of essential oils (viz. cinnamaldehyde and cuminaldehyde) and aromatic amines (viz 2-aminophenol and 4-aminoantipyrene) towards the facial tricarbonylrhenium(I) core. The resultant rhenium(I) compounds: (mu-X)(2)[Re(CO)(3)](2) where X = 2[3-Phenylprop-2-en-1-ylidene]amino}phenol (ciap) (for 1) or 2-[4-(propan-2-yl)benzylidene]amino}phenol (cuap) (for 2), fac-[Re(CO)(3)(apy)Cl] (apy = 4-aminoantipyrene) (3) and fac-[Re(CO)(3)(cinap)Cl] (cinap = 1,5-dimethyl-2-phenyl-4-[3-phenylprop-2-en-1-ylidene]amino}-1,2-dihydro-3H-pyrazol-3-one) (4) were formed. The metal compounds were spectroscopically characterized and structural elucidations were confirmed by single crystal X-ray diffraction. DFT studies were utilized to rationalize the contrasting coordination behaviours of the structural analogues, 1,5-dimethyl-2-phenyl-4-[4-(propan-2-yl)benzylidene]amino}-1,2-dihydro-3H-pyrazol-3-one (cumap) and cinap in the formation of 3 and 4, respectively. These metal compounds showed affinities towards Calf-Thymus DNA based on UV-Vis DNA binding titrations and molecular docking studies revealed that they are groove binders. In addition, gel electrophoresis experiments indicated that steric factors has an influence on the DNA cleavage activities of the mono- and dinuclear rhenium(I) compounds. (C) 2018 Elsevier B.V. All rights reserved.
• Preparation and Biological Activities of Novel Cuminaldehyde Derivatives
  作者：Pardeep Kaur、Sunita Sharma、Jyoti Gaba

  DOI：10.1080/00304948.2020.1871574

  日期：2021.5.4

  (2021). Preparation and Biological Activities of Novel Cuminaldehyde Derivatives. Organic Preparations and Procedures International: Vol. 53, No. 3, pp. 240-253.

  （2021年）。新型孜然醛衍生物的制备及其生物活性。国际有机制剂和程序：Vol。53，第3号，第240-253页。