2-furaldehyde-4-phenylthiosemicarbazone | 920339-22-6

• 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: 2-furaldehyde-4-phenylthiosemicarbazone
• 英文别名: (E)-2-(furan-2-ylmethylene)-N-phenylhydrazine-1-carbothioamide；1-(furan-2-ylmethylene)-4-phenylthiosemicarbazone；2-Furaldehyde, 4-phenylthiosemicarbazone；1-[(E)-furan-2-ylmethylideneamino]-3-phenylthiourea
• CAS: 920339-22-6
• 化学式: C₁₂H₁₁N₃OS
• 分子量: 245.305
• InChiKey: VEVZWLDVAFRIQA-UKTHLTGXSA-N

物化性质

• 熔点：
  129-131 °C(Solv: acetone (67-64-1))
• 沸点：
  370.2±34.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.56
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  palladium(II) chloride dihydrate 、 2-furaldehyde-4-phenylthiosemicarbazone 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以84%的产率得到palladium(II)[(2-furaldehyde-4-phenylisothiosemicarbazone(1-))]2
  参考文献：
  名称：

  Synthesis, characterization and crystal structures of nickel(II), palladium(II) and copper(II) complexes with 2-furaldehyde-4-phenylthiosemicarbazone

  摘要：

  2-Furaldehyde-4-phenylthiosemicarbazone (HL) and its nickel(II), palladium(II) and copper(II) complexes: [Pd(L)(2)] (1), [Ni(L)(2)] (2), [Cu-2(L)(2)(Et3N)(2)(H2O)(4) ](SO4) (3), [Cu-2(L)(2)(Et3N)(2)(H2O)(4) ](NO3)(2) (4), [Cu(L)(2)(H2O)(2)] (5), [Cu(L)(OAc)(H2O)] (6) were synthesized and characterized. The ligand has been characterized by elemental analyses, IR, electronic, H-1 NMR and C-13 NMR spectroscopy. The bidentate nature of the ligand is evident from the IR spectra.The nickel(II), palladium(II) and copper(II) complexes have been characterized by different physicochemical techniques like molar conductivity, magnetic susceptibility measurements, electronic, infrared and EPR spectral studies. For the copper(II) complexes metalligand bonding parameters have been evaluated from the EPR spectra. These parameters indicate the presence out-of-plane pi bonding.In addition, the structures of the ligand, nickel(II) and palladium(II) complexes have been determined by single-crystal X-ray diffraction. These complexes crystallized into triclinic lattices with space group P1. The metal ion is coordinated through the sulfur atom and the azomethine nitrogen atom. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.12.030
• 作为产物：
  描述：

  硫代异氰酸苯酯 在 hydrazine hydrate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 2-furaldehyde-4-phenylthiosemicarbazone
  参考文献：
  名称：

  Thiosemicarbazone-based lead optimization to discover high-efficiency and low-toxicity anti-gastric cancer agents

  摘要：

  In this paper, a series of thiosemicarbazone derivatives containing different aromatic heterocyclic groups were synthesized and the tridentate donor system of the lead compound was optimized. Most of the target compounds showed improved antiproliferative activity against MGC803 cells. SAR studies revealed that compound 5d displayed significant advantages in inhibition effect with an IC50 value of 0.031 mu M, and better selectivity between cancer and normal cells than 3-AP and DpC (about 15- and 5-fold improved respectively). Besides, compound 5d showed selective antiproliferative activity in not only other cancer cells but also different gastric cancer cell lines. In-depth mechanism studies showed that compound 5d could induce mitochondria-related apoptosis which might be related to the elevation of intracellular ROS level, and cause cell cycle arrest at S phase. Moreover, 5d could evidently suppress the cell migration and invasion by blocking the EMT (epithelial-mesenchymal transition) process. Consequently, our studies provided a lead optimization strategy of thiosemicarbazone derivatives which would contribute to discover high-efficiency and low-toxicity agents for the treatment of gastric cancer. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112349

文献信息

• Synthesis, Crystal Structures and Fluorescence Properties of Ni (II) and Cu (II) Complexes with 1-(Furan-2-ylmethylene)-4-phenylthiosemicarbazone
  作者：Ping Ping Sun、Fang Fang Jian、Xian Wang

  DOI：10.1007/s10870-009-9595-z

  日期：2010.1

  Two coordination complexes, NiL 2 and CuL 2 L = bis[1-(furan-2-ylmethylene)-4-phenylthiosemicarbazone]}, were synthesized and determined by X-ray crystallography. Both crystallize in the Orthorhombic system, space group Pbcn, with lattice parameters: a = 11.935 (2) Å, b = 15.314(3) Å, c = 12.952(3) Å and Z = 4 for Ni (II); a = 20.850(4) Å, b = 15.049(3) Å, c = 7.5633(5) Å and Z = 4 for Cu (II). In both complexes, the central metal atom is coordinated in a distorted square-planar with two ligands through two S and N atoms, respectively. The EA, UV, IR and TG-DTG were studied and the possible structures of the complexes were speculated. Moreover, the fluorescence of the complexes were studied. The results reveal that copper complex can emit purple fluorescence in solvents. Two coordination complexes, NiL2 and CuL2 L = bis[1-(furan-2-ylmethylene)-4-phenylthiosemicarbazone]}, were synthesized and determined by X-ray crystallography. In both complexes, the central metal atom is coordinated in a distorted square-planar with two ligands L through two S and N atoms, respectively.

  两种配位化合物NiL2和CuL2L=双[1-(呋喃-2-亚甲基)-4-苯基氨基脲]}被合成并通过X射线晶体学确定。两者均呈正交晶系，空间群为Pbcn，晶格参数为：对于Ni(II)，a=11.935(2) Å，b=15.314(3) Å，c=12.952(3) Å，Z=4；对于Cu(II)，a=20.850(4) Å，b=15.049(3) Å，c=7.5633(5) Å，Z=4。在这两种配合物中，中心金属原子都以扭曲的四方平面形式通过两个S和N原子与两个配体L配位。研究了EA、UV、IR和TG-DTG，并推测了配合物可能的结构。此外，还研究了配合物的荧光性质。结果表明，铜配合物在溶剂中能发出紫色荧光。两种配位化合物NiL2和CuL2L=双[1-(呋喃-2-亚甲基)-4-苯基氨基脲]}被合成并通过X射线晶体学确定。在这两种配合物中，中心金属原子都以扭曲的四方平面形式通过两个S和N原子与两个配体L配位。
• MARTVON A.; STANKOVSKY S.; UHER M., CHEM. 2VESTI, 1980, 34, NO 1, 118-124
  作者：MARTVON A.、 STANKOVSKY S.、 UHER M.

  DOI：——

  日期：——
• Synthesis, characterization and crystal structures of nickel(II), palladium(II) and copper(II) complexes with 2-furaldehyde-4-phenylthiosemicarbazone
  作者：Diana-Carolina Ilies、Elena Pahontu、Sergiu Shova、Aurelian Gulea、Tudor Rosu

  DOI：10.1016/j.poly.2012.12.030

  日期：2013.3

  2-Furaldehyde-4-phenylthiosemicarbazone (HL) and its nickel(II), palladium(II) and copper(II) complexes: [Pd(L)(2)] (1), [Ni(L)(2)] (2), [Cu-2(L)(2)(Et3N)(2)(H2O)(4) ](SO4) (3), [Cu-2(L)(2)(Et3N)(2)(H2O)(4) ](NO3)(2) (4), [Cu(L)(2)(H2O)(2)] (5), [Cu(L)(OAc)(H2O)] (6) were synthesized and characterized. The ligand has been characterized by elemental analyses, IR, electronic, H-1 NMR and C-13 NMR spectroscopy. The bidentate nature of the ligand is evident from the IR spectra.The nickel(II), palladium(II) and copper(II) complexes have been characterized by different physicochemical techniques like molar conductivity, magnetic susceptibility measurements, electronic, infrared and EPR spectral studies. For the copper(II) complexes metalligand bonding parameters have been evaluated from the EPR spectra. These parameters indicate the presence out-of-plane pi bonding.In addition, the structures of the ligand, nickel(II) and palladium(II) complexes have been determined by single-crystal X-ray diffraction. These complexes crystallized into triclinic lattices with space group P1. The metal ion is coordinated through the sulfur atom and the azomethine nitrogen atom. (C) 2013 Elsevier Ltd. All rights reserved.
• Thiosemicarbazone-based lead optimization to discover high-efficiency and low-toxicity anti-gastric cancer agents
  作者：Xin-Hui Zhang、Bo-Wang、Yuan-Yuan Tao、Qin Ma、Hao-Jie Wang、Zhang-Xu He、Hui-Pan Wu、Yi-Han Li、Bing Zhao、Li-Ying Ma、Hong-Min Liu

  DOI：10.1016/j.ejmech.2020.112349

  日期：2020.8

  In this paper, a series of thiosemicarbazone derivatives containing different aromatic heterocyclic groups were synthesized and the tridentate donor system of the lead compound was optimized. Most of the target compounds showed improved antiproliferative activity against MGC803 cells. SAR studies revealed that compound 5d displayed significant advantages in inhibition effect with an IC50 value of 0.031 mu M, and better selectivity between cancer and normal cells than 3-AP and DpC (about 15- and 5-fold improved respectively). Besides, compound 5d showed selective antiproliferative activity in not only other cancer cells but also different gastric cancer cell lines. In-depth mechanism studies showed that compound 5d could induce mitochondria-related apoptosis which might be related to the elevation of intracellular ROS level, and cause cell cycle arrest at S phase. Moreover, 5d could evidently suppress the cell migration and invasion by blocking the EMT (epithelial-mesenchymal transition) process. Consequently, our studies provided a lead optimization strategy of thiosemicarbazone derivatives which would contribute to discover high-efficiency and low-toxicity agents for the treatment of gastric cancer. (C) 2020 Elsevier Masson SAS. All rights reserved.