Crystal structures and anticancer activities of five novel pyrazolone-enamine transition metal complexes with 4-benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one

Publication date: 5 November 2018
Source:Journal of Molecular Structure, Volume 1171
Author(s): Ziao Zong, Xiaodan Wei, Xingchen Yan, Yuhua Fan
Three pyrazolone-enamine ligands HL¹, HL² and H2L³ were synthesized by the reaction of 4-benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one (HPMBP) with methyl 4-aminophenylacetate, 4-aminobenzamide and 2-amino-5-methylphenol, respectively, followed by tautomeric reactions. Their complexes [Zn(L¹)2] (1), [Co(L²)2(H2O)2] (2), [CuL³(H2O)2] (3a), [ZnL³(H2O)2] (3b) and [CdL³(H2O)2] (3c) were synthesized and characterized by single-crystal X-ray, IR, elemental analysis, ¹H NMR, TG analysis. Single-crystal X-ray analysis reveals that HL¹, complex 1 and complex 2 are all connected by hydrogen bonds, CH···π interactions and van der Waals forces to form the 3-D network. The Zn(II) ion in complex 1 is four coordinated to two L¹ ligands. The Co(II) ion in complex 2 is six coordinated to two L² ligands and two water molecules. The metal ions in complexes 3a, 3b and 3c are five coordinated to one L³ ligand and two water molecules. After coordination, the structures of the ligands reversed to the Schiff base structures. Moreover, the anticancer activities were investigated, the results show that complexes 3a and 3b can effectively inhibit the proliferation of human breast cancer MDA-MB-231 cells. Besides, complexes 1, 2, 3b and 3c exhibit excellent luminescence properties.



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