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.
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 (1)H nuclear magnetic resonance (NMR) analysis and DFT calculations. The obtained results have been compared with those from other studies of similar compounds.
Ciolkowski
Michal
M
Department of Cosmetic Raw Materials Chemistry, Medical University of Lodz, Lodz, Poland.
Paneth
Piotr
P
Lorenz
Ingo-Peter
IP
Mayer
Peter
P
Rozalski
Marek
M
Krajewska
Urszula
U
Budzisz
Elzbieta
E
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002413:Cations, Divalent / Q000737:chemistry; D045744:Cell Line, Tumor; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D010165:Palladium / Q000737:chemistry*; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011789:Quantum Theory; D012997:Solvents / Q000737:chemistry; D013816:Thermodynamics
C548343:1H-(2'-pyridyl)-3-methyl-5-hydroxypyrazole; C548344:1H-(2'-pyridyl)-3-phenyl-5-hydroxypyrazole; D000970:Antineoplastic Agents; D002413:Cations, Divalent; D011720:Pyrazoles; D011725:Pyridines; D012997:Solvents; D010165:Palladium