1,1’-(1E,1’E)-{(4-methyl-1,2-phenylene)bis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)dinaphthalen-2-ato-κ⁴ONN’O’}copper(II) | 200071-61-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,1’-(1E,1’E)-{(4-methyl-1,2-phenylene)bis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)dinaphthalen-2-ato-κ⁴ONN’O’}copper(II)
• CAS: 200071-61-0
• 化学式: C₂₉H₂₀CuN₂O₂
• 分子量: 492.036
• InChiKey: XJCJORJOWWYGHO-VRWUNRENSA-L

反应信息

• 作为产物：
  描述：

  3,4-二氨基甲苯 、 2-羟基-1-萘甲醛 、 copper dichloride 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以69.91%的产率得到1,1’-(1E,1’E)-{(4-methyl-1,2-phenylene)bis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)dinaphthalen-2-ato-κ⁴ONN’O’}copper(II)
  参考文献：
  名称：

  Synthesis of metal(II) [M = Cu, Mn, Zn] Schiff base complexes and their Pro-apoptotic activity in liver tumor cells via caspase activation

  摘要：

  Hepatocellular carcinoma is the fifth most common cancer responsible for more than 600,000 deaths per year. It is a typical vascular tumor which at earlier stages does not exhibit remarkable development of tumor; however, at advance stages, it is richly supplied by blood vessels and damages hepatocyte, the main functional cell types in the liver. Currently, surgery and chemotherapy are the main treatment strategies. However, the chemotherapeutic agents are usually unable to discriminate between normal and cancerous cells, and hence adverse effects of drug toxicities have become the major concerns in chemotherapy. Thus, inducing caspase dependent cytotoxicity in cancer cells via apoptosis has become one of the interesting and effective strategies for fighting this disease. The current study is an effort to further explore this area of research. Mn(II), Cu(II), and Zn(II) Schiff base complexes were prepared by condensation of 2-hydroxy-1-naphthaldehyde with either 4-nitrobenzene-1,2-diamine or 4-methylbenzene-1,2-diamine and characterized by Spectroscopic (FT-IR, UV-Vis, NMR, and MS) and microanalysis. The ligands, in comparison to their metal complexes, were evaluated for their anticancer and proapoptotic properties in human hepatocarcinoma (HepG2) cells. Results showed that the complexes are more potent proapoptotic agents than the parent ligands. All the tested compounds showed dose-dependent antiproliferative activity comparable with 5-fluorouracil (IC50 = 4.6 mu g/mL). All the synthesized Schiff base ligands and respective metal complexes showed potential anticancer activity. Out of them, some compounds showed IC50 value as low as 1.24-3.56 mu g/mL. Compounds 3 and 7 inhibited HepG2 cell proliferation by inducing apoptosis via activation of caspase cascade.

  DOI：

  10.1007/s00044-013-0482-y