Ni(salicylaldehyde thiosemicarbazone(-2H))(triphenylphosphine)

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ni(salicylaldehyde thiosemicarbazone(-2H))(triphenylphosphine)
• 英文别名: nickel(2+);N'-[(E)-(2-oxidophenyl)methylideneamino]carbamimidothioate;triphenylphosphane
• 化学式: C₂₆H₂₂N₃NiOPS
• 分子量: 514.21
• InChiKey: KZNBBHXYWJOBLD-ATWZUJJXSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Ni2(salicylaldehyde thiosemicarbazone(-2H))2 、 三苯基膦 以 乙醇 为溶剂， 反应 3.0h， 以74%的产率得到Ni(salicylaldehyde thiosemicarbazone(-2H))(triphenylphosphine)
  参考文献：
  名称：

  Nickel complexes of some thiosemicarbazones: Synthesis, structure, catalytic properties and cytotoxicity studies

  摘要：

  Reaction of salicylaldehyde thiosemicarbazone (H2L1), 2-hydroxyacetophenone thiosemicarbazone (H2L2) and 2-hydroxynaphthaldehyde thiosemicarbazone (H2L3) with Ni(ClO4)(2)center dot 6H(2)O afforded dimeric complexes of type [{Ni(L)} 2]. Reaction of these complexes with triphenylphosphine (PPh3), pyridine (py) and 4,4'-bipyridine (bpy) has yielded complexes of type [Ni(L)(PPh3)], [Ni(L)(py)] and [{Ni(L)}(2)(bpy)], respectively, which have also been obtained from reaction of the thiosemicarbazones with Ni(ClO4)2 center dot 6H(2)O and PPh3 or pyridine or 4,4'-bipyridine. Structures of the [{Ni(L)}(2)] complexes have been optimized by DFT calculations. Crystal structures of [Ni(L-2)(PPh3)], [Ni(L-2)(py)] and [{Ni(L-1)}(2)(bpy)] have been determined. In all these complexes thiosemicarbazone is coordinated to nickel as ONS-donor. All these complexes show characteristic H-1 NMR spectra and intense absorptions in the visible and ultraviolet region. Cyclic voltammetry on the complexes shows one irreversible oxidation on the positive side of SCE, and one irreversible reduction on the negative side. The mixed-ligand nickel complexes are found to be efficient catalysts for Heck type C-C coupling reactions. In vitro cytotoxicity screenings of the six mononuclear nickel complexes have been also carried out in a human tumor cell lines, viz. breast carcinoma cell line (MCF-7). [Ni(L-3)(py)] shows the lowest LD50 value. An apoptosis study in MCF-7 with all the complexes confirms that at concentrations near LD50 they induce apoptosis. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.05.034
• 作为试剂：
  描述：

  丙烯酸丁酯 、 对溴苯甲醛 在 Ni(salicylaldehyde thiosemicarbazone(-2H))(triphenylphosphine) 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 butyl 3-(4-formylphenyl)acrylate
  参考文献：
  名称：

  Nickel complexes of some thiosemicarbazones: Synthesis, structure, catalytic properties and cytotoxicity studies

  摘要：

  Reaction of salicylaldehyde thiosemicarbazone (H2L1), 2-hydroxyacetophenone thiosemicarbazone (H2L2) and 2-hydroxynaphthaldehyde thiosemicarbazone (H2L3) with Ni(ClO4)(2)center dot 6H(2)O afforded dimeric complexes of type [{Ni(L)} 2]. Reaction of these complexes with triphenylphosphine (PPh3), pyridine (py) and 4,4'-bipyridine (bpy) has yielded complexes of type [Ni(L)(PPh3)], [Ni(L)(py)] and [{Ni(L)}(2)(bpy)], respectively, which have also been obtained from reaction of the thiosemicarbazones with Ni(ClO4)2 center dot 6H(2)O and PPh3 or pyridine or 4,4'-bipyridine. Structures of the [{Ni(L)}(2)] complexes have been optimized by DFT calculations. Crystal structures of [Ni(L-2)(PPh3)], [Ni(L-2)(py)] and [{Ni(L-1)}(2)(bpy)] have been determined. In all these complexes thiosemicarbazone is coordinated to nickel as ONS-donor. All these complexes show characteristic H-1 NMR spectra and intense absorptions in the visible and ultraviolet region. Cyclic voltammetry on the complexes shows one irreversible oxidation on the positive side of SCE, and one irreversible reduction on the negative side. The mixed-ligand nickel complexes are found to be efficient catalysts for Heck type C-C coupling reactions. In vitro cytotoxicity screenings of the six mononuclear nickel complexes have been also carried out in a human tumor cell lines, viz. breast carcinoma cell line (MCF-7). [Ni(L-3)(py)] shows the lowest LD50 value. An apoptosis study in MCF-7 with all the complexes confirms that at concentrations near LD50 they induce apoptosis. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.05.034

文献信息

• One pot synthesis of structurally different mono and dimeric Ni(ii) thiosemicarbazone complexes and N-arylation on a coordinated ligand: a comparative biological study
  作者：R. Prabhakaran、P. Kalaivani、P. Poornima、F. Dallemer、G. Paramaguru、V. Vijaya Padma、R. Renganathan、R. Huang、K. Natarajan

  DOI：10.1039/c2dt12231f

  日期：——

  One pot synthesis of three structurally different Ni(II) thiosemicarbazone complexes 1, 2 and 3 were obtained from the reaction between [NiCl2(PPh3)2], 1,2-bis(diphenylphosphino)ethane, and [H2-(Sal-tsc)]. The obtained products were characterized by various spectral and analytical techniques. From the X-ray crystallographic analysis, an unexpected N-arylation on the coordinated salicylaldehydethiosemicarbazone was found in complex 2. The comparative biological evolutions such as DNA/protein binding, antioxidant, cytotoxicity (MTT, LDH, and NO) and cellular uptake studies have been examined for [Ni(Sal-tsc)(PPh3)] (1) and [(Ni(Sal-tsc))2(μ-dppe)] (3). When comparing the cytotoxicity of the complexes, 1 exhibited higher activity than 2 and 3 and by comparing with standard cis-platin, both of them were found to exhibit better activity under identical conditions.

  通过[NiCl2(PPh3)2]、1,2-双(二苯基膦)乙烷和[H2-(Sal-tsc)的反应，一锅法合成了三种结构不同的Ni(II)缩氨基硫脲配合物1、2和3。 )]。通过各种光谱和分析技术对所得产物进行了表征。通过 X 射线晶体分析，在配合物 2 中发现了配位的水杨醛缩氨基硫脲上意外的 N-芳基化。DNA/蛋白质结合、抗氧化剂、细胞毒性（MTT、LDH 和 NO）和细胞摄取等比较生物进化研究表明，已检查 [Ni(Sal-tsc)(PPh3)] (1) 和 [(Ni(Sal-tsc))2(μ-dppe)] (3)。当比较复合物的细胞毒性时，1比2和3表现出更高的活性，并且通过与标准顺铂比较，发现它们在相同条件下都表现出更好的活性。
• Baral, Minati; Kanungo, B. K.; Pradhan, B., Journal of the Indian Chemical Society, 1986, vol. 63, p. 1018 - 1020
  作者：Baral, Minati、Kanungo, B. K.、Pradhan, B.

  DOI：——

  日期：——
• Nickel complexes of some thiosemicarbazones: Synthesis, structure, catalytic properties and cytotoxicity studies
  作者：Sayanti Datta、Dipravath Kumar Seth、Sudeshna Gangopadhyay、Parimal Karmakar、Samaresh Bhattacharya

  DOI：10.1016/j.ica.2012.05.034

  日期：2012.9

  Reaction of salicylaldehyde thiosemicarbazone (H2L1), 2-hydroxyacetophenone thiosemicarbazone (H2L2) and 2-hydroxynaphthaldehyde thiosemicarbazone (H2L3) with Ni(ClO4)(2)center dot 6H(2)O afforded dimeric complexes of type [Ni(L)} 2]. Reaction of these complexes with triphenylphosphine (PPh3), pyridine (py) and 4,4'-bipyridine (bpy) has yielded complexes of type [Ni(L)(PPh3)], [Ni(L)(py)] and [Ni(L)}(2)(bpy)], respectively, which have also been obtained from reaction of the thiosemicarbazones with Ni(ClO4)2 center dot 6H(2)O and PPh3 or pyridine or 4,4'-bipyridine. Structures of the [Ni(L)}(2)] complexes have been optimized by DFT calculations. Crystal structures of [Ni(L-2)(PPh3)], [Ni(L-2)(py)] and [Ni(L-1)}(2)(bpy)] have been determined. In all these complexes thiosemicarbazone is coordinated to nickel as ONS-donor. All these complexes show characteristic H-1 NMR spectra and intense absorptions in the visible and ultraviolet region. Cyclic voltammetry on the complexes shows one irreversible oxidation on the positive side of SCE, and one irreversible reduction on the negative side. The mixed-ligand nickel complexes are found to be efficient catalysts for Heck type C-C coupling reactions. In vitro cytotoxicity screenings of the six mononuclear nickel complexes have been also carried out in a human tumor cell lines, viz. breast carcinoma cell line (MCF-7). [Ni(L-3)(py)] shows the lowest LD50 value. An apoptosis study in MCF-7 with all the complexes confirms that at concentrations near LD50 they induce apoptosis. (C) 2012 Elsevier B. V. All rights reserved.