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钌(II)-芳基配合物与功能化吡啶:合成、表征和细胞毒性活性。

Ruthenium(II)-arene complexes with functionalized pyridines: synthesis, characterization and cytotoxic activity.

机构信息

Faculty of Chemistry, University of Belgrade, Studentski trg 12-16, 11000 Belgrade, Serbia.

出版信息

Eur J Med Chem. 2010 Mar;45(3):1051-8. doi: 10.1016/j.ejmech.2009.11.055. Epub 2009 Dec 16.

DOI:10.1016/j.ejmech.2009.11.055
PMID:20053483
Abstract

Ruthenium(II)-arene complexes of general formulae [(eta(6)-p-cymene)Ru(L(1-3))Cl(2)], where L(1-3) is 3-acetylpyridine (1), 4-acetylpyridine (2) and 2-amino-5-chloropyridine (3), correspondingly, [(eta(6)-p-cymene)Ru(HL(4,5))Cl(2)], where HL(4) and HL(5) are respectively isonicotinic acid (4) and nicotinic acid (5) and [(eta(6)-p-cymene)Ru(HL(6-9))Cl], where H(2)L(6-9) represent 2,3-pyridinedicarboxylic acid (6), 2,4-pyridinedicarboxylic acid (7), 2,5-pyridinedicarboxylic acid (8) and 2,6-pyridinedicarboxylic acid (9), were prepared by the reaction of (eta(6)-p-cymene)(2)RuCl(2) (10) with the corresponding ligand in 1:2 molar ratio in isopropanol. The complexes were characterized by elemental analysis, mass spectrometry, IR and NMR spectroscopies. According to these data the molecules adopt the usual "three-leg piano-stool" geometry which is common for this type of complexes. The structures of 1 and 7 were determined by X-ray crystallography. The complexes revealed low antiproliferative activity in six investigated tumor cell lines (HeLa, B16, FemX, MDA-MB-361, MDA-MB-453 and LS-174). The reaction of 6 with 9-methyladenine was studied by (1)H NMR, (1)H, (1)H COSY and (1)H, (1)H NOESY spectroscopy.

摘要

通式为[(eta(6)-p-cymene)Ru(L(1-3))Cl(2)]的钌(II)-芳族配合物,其中 L(1-3)分别为 3-乙酰基吡啶 (1)、4-乙酰基吡啶 (2)和 2-氨基-5-氯吡啶 (3),[(eta(6)-p-cymene)Ru(HL(4,5))Cl(2)],其中 HL(4)和 HL(5)分别为异烟酸 (4)和烟酸 (5),[(eta(6)-p-cymene)Ru(HL(6-9))Cl],其中 H(2)L(6-9)代表 2,3-吡啶二甲酸 (6)、2,4-吡啶二甲酸 (7)、2,5-吡啶二甲酸 (8)和 2,6-吡啶二甲酸 (9),是通过 (eta(6)-p-cymene)(2)RuCl(2) (10)与相应配体在异丙醇中以 1:2 摩尔比反应制备的。这些配合物通过元素分析、质谱、IR 和 NMR 光谱进行了表征。根据这些数据,分子采用了常见的“三腿钢琴凳”几何形状,这是此类配合物的常见形状。1 和 7 的结构通过 X 射线晶体学确定。这些配合物在六种肿瘤细胞系(HeLa、B16、FemX、MDA-MB-361、MDA-MB-453 和 LS-174)中表现出低的抗增殖活性。通过 (1)H NMR、(1)H、(1)H COSY 和 (1)H、(1)H NOESY 光谱研究了 6 与 9-甲基腺嘌呤的反应。

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