2-(diphenylphosphino)benzaldehyde 4-phenylsemicarbazone | 1092936-90-7

• 英文名称: 2-(diphenylphosphino)benzaldehyde 4-phenylsemicarbazone
• 英文别名: 1-[(2-diphenylphosphanylphenyl)methylideneamino]-3-phenylurea
• CAS: 1092936-90-7
• 化学式: C₂₆H₂₂N₃OP
• 分子量: 423.454
• InChiKey: AAOXTDZKJKIYNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  sodium isocyanate 、 nickel(II) tetrafluoroborate hexahydrate 、 2-(diphenylphosphino)benzaldehyde 4-phenylsemicarbazone 以 乙醇 为溶剂， 反应 2.0h， 以68%的产率得到Ni(2-(diphenylphosphino)benzaldehyde 4-phenylsemicarbazone)OCN
  参考文献：
  名称：

  Synthesis, characterization, DFT calculation and biological activity of square-planar Ni(II) complexes with tridentate PNO ligands and monodentate pseudohalides. Part II

  摘要：

  Three square-planar complexes of Ni(II) with condensation derivative of 2-(diphenylphosphino)benzaldehyde and 4-phenylsemicarbazide and monodentate pseudohalides have been synthesized and characterized on the basis of the results of X-ray, NMR and IR spectroscopy and elemental analysis. Investigated complexes exhibited moderate antibacterial and cytotoxic activity. The most pronounced cytotoxic activity (in the range of cisplatin) to HeLa cell line was observed for ligand and all the complexes. Azido complex and ligand induced concentration dependent cell cycle arrest in the S phase, as well as decrease of percentage of cells in G1 phase, without significant increase of apoptotic fraction of cells. The interaction of the azido complex and ligand with CT-DNA results in changes in UV-Vis spectra typical for non-covalent bonding. The observed intrinsic binding constant of azido complex-CT-DNA and ligand-CT-DNA were 3.22 × 10(5) M(-1) and 2.79 × 10(5) M(-1). The results of DNA cleavage experiments showed that azido complex nicked supercoiled plasmid DNA.

  DOI：

  10.1016/j.ejmech.2014.06.079
• 作为产物：
  描述：

  2-二苯基膦苯甲醛 、 4-苯基氨基脲 以 乙醇 为溶剂， 生成 2-(diphenylphosphino)benzaldehyde 4-phenylsemicarbazone
  参考文献：
  名称：

  Investigation of antitumor potential of Ni(II) complexes with tridentate PNO acylhydrazones of 2-(diphenylphosphino)benzaldehyde and monodentate pseudohalides

  摘要：

  Square-planar azido Ni(II) complex with condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent was synthesized and its crystal structure was determined. Cytotoxic activity of the azido complex and previously synthesized isothiocyanato, cyanato and chlorido Ni(II) complexes with this ligand was examined on six tumor cell lines (HeLa, A549, K562, MDA-MB-453, MDA-MB-361 and LS-174) and two normal cell line (MRC-5 and BEAS-2B). All the investigated nickel(II) complexes were cytotoxic against all tumor cell lines. The newly synthesized azido complex showed selectivity to HeLa and A549 tumor cell lines compared to the normal cells (for A549 IC50 was similar to that of cisplatin). Azido complex interferes with cell cycle phase distribution of A549 and HeLa cells and possesses nuclease activity towards supercoiled DNA. The observed selectivity of the azido complex for some tumor cell lines can be connected with its strong DNA damaging activity.

  DOI：

  10.1007/s00775-015-1315-x

文献信息

• Chloro-2-(diphenylphosphino)benzaldehyde 4-phenylsemicarbazonato-P, N, N′)methoxooxorhenium(V) – a Semicarbazone Complex with an Unusual Coordination Mode
  作者：Ali Barandov、Ulrich Abram

  DOI：10.1002/zaac.200700268

  日期：2007.9

  (NBu4)[ReOCl4] reacts with 2-(diphenylphosphino)benzaldehyde 4-phenylsemicarbazone (HL1) in methanol under formation of the red rhenium(V) complex [ReO(Cl)(OMe)(L1)]. The semicarbazonato ligand is singly deprotonated and coordinates meridionally via the phosphorus atom and two nitrogen atoms. This unusual coordination mode of a semicarbazone is confirmed by IR and NMR spectroscopy and by the solid

  (NBu4) [ReOCl4] 在甲醇中与 2-（二苯基膦基）苯甲醛 4-苯基缩氨基脲 (HL1) 反应，形成红色铼 (V) 络合物 [ReO (Cl) (OMe) (L1)]。缩氨基配体单独去质子化并通过磷原子和两个氮原子经向配位。通过红外和核磁共振光谱以及产物的固态结构证实了缩氨基脲的这种不寻常的配位模式。