(Pyrazolylmethyl)pyridine platinum(II) and gold(III) complexes: Synthesis, structures and evaluation as anticancer agents

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• 作者：Tebogo V. Segapelo ; Ilia A. Guzei ; Lara C. Spencer ; Werner E Van Zyl ; James Darkwa
• 关键词：(Pyrazol-1-ylmethyl)pyridine ligands ; Platinum complexes ; Gold complexes ; C– ; H activation ; Antitumor activity
• 刊名：Inorganica Chimica Acta
• 出版年：2009
• 出版时间：1 July 2009
• 年：2009
• 卷：362
• 期：9
• 页码：3314-3324
• 全文大小：721 K

文摘

Reactions of 2-(3,5-dimethylpyrazol-1-ylmethyl)pyridine (L1), 2-(3,5-diphenylpyrazol-1-ylmethyl)pyridine (L2), 2-(3,5-di-tert-butylpyrazol-1-ylmethyl)pyridine (L3) and 2-(3-p-tolylpyrazol-1-ylmethyl)pyridine (L4) with K₂[PtCl₄] in a mixture of ethanol and water formed the dichloro platinum complexes [PtCl₂(L1)] (1), [PtCl₂(L2)] (2), [PtCl₂(L3)] (3) and [PtCl₂(L4)] (4). Complex 1, [PtCl₂(L1)], could also be prepared in a mixture of acetone and water. Performing the reactions of L2 and L3 in a mixture of acetone and water, however, led to C–H activation of acetone under mild conditions to form the neutral acetonyl complexes [Pt(CH₂COCH₃)Cl(L2)] (2a) and [Pt(CH₂COCH₃)Cl(L3)] (3a). The same ligands reacted with HAuCl₄ · 4H₂O in a mixture of ethanol and water to form the gold salts [AuCl₂(L1)][AuCl₄] (5) [AuCl₂(L2)][Cl] (6) [AuCl₂(L3)][Cl] (7) and [AuCl₂(L4)][AuCl₄] (8); however, with the pyrazolyl unit in the para position of the pyridinyl ring in 4-(3,5-dimethylpyrazol-1-ylmethyl)pyridine (L5), 4-(3,5-diphenylpyrazol-1-ylmethyl)pyridine (L6) neutral gold complexes [AuCl₃(L5)] (9) and [AuCl₂(L6)] (10) were formed; signifying the role the position of the pyrazolyl group plays in product formation in the gold reactions. X-ray crystallographic structural determination of L6, 2, 3 3a, 8 and 10 were very important in confirming the structures of these compounds; particularly for 3a and 8 where the presence of the acetonyl group confirmed C–H activation and for 8 where the counter ion is . Cytotoxicity studies of L2, L4 and complexes 1–10 against HeLa cells showed the Au complexes were much less active than the Pt complexes.