Tautomeric forms study of 1H-(2′-pyridyl)-3-methyl-5-hydroxypyrazole and 1H-(2′-pyridyl)-3-phenyl-5-hydroxypyrazole. Synthesis, structure, and cytotoxic activity of their complexes with palladium(II) ions

被引:14
作者
Ciolkowski, Michal [1 ]
Paneth, Piotr [2 ]
Lorenz, Ingo-Peter [3 ]
Mayer, Peter [3 ]
Rozalski, Marek [4 ]
Krajewska, Urszula [4 ]
Budzisz, Elzbieta [1 ]
机构
[1] Med Univ Lodz, Fac Pharm, Dept Cosmet Raw Mat Chem, PL-90151 Lodz, Poland
[2] Tech Univ Lodz, Dept Chem, Inst Appl Radiat Chem, PL-90924 Lodz, Poland
[3] Univ Munich, Dept Chem & Biochem, Munich, Germany
[4] Med Univ Lodz, Fac Pharm, Dept Pharmaceut Biochem, PL-90151 Lodz, Poland
关键词
Palladium(II) complexes; antitumor agents; density functional calculations; tautomerism; POLARIZABLE CONTINUUM MODEL; MOLECULAR-ORBITAL METHODS; X-RAY-STRUCTURE; CRYSTAL-STRUCTURE; HETEROAROMATIC-COMPOUNDS; PLATINUM COMPOUNDS; PD(II) COMPLEXES; 5-MEMBERED RINGS; PT(II); DERIVATIVES;
D O I
10.3109/14756360902827653
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
In this article the synthesis of new 1H-(2'-pyridyl)-3-methyl-5-hydroxypyrazole and 1H-(2'-pyridyl)-3-phenyl-5-hydroxypyrazole complexes with palladium(II) ions is reported. The structures of obtained compounds have been characterized by X-ray crystallography and DFT (density functional theory) calculations. The cytotoxicity of complexes and ligands has been examined for two human leukemia cell lines (HL-60 and NALM-6) and one human melanoma cell line (WM-115). The palladium(II) complex with 1H-(2'-pyridyl)-3-phenyl-5-hydroxypyrazole has been shown to possess greater activity than carboplatin against the WM-115 melanoma cell line. Additionally, the ligands' tautomeric forms existence in different solvents (chloroform, methanol, DMSO) has been characterized by H-1 nuclear magnetic resonance (NMR) analysis and DFT calculations. The obtained results have been compared with those from other studies of similar compounds.
引用
收藏
页码:1257 / 1268
页数:12
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