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首页> 外文期刊>Dalton transactions: An international journal of inorganic chemistry >Synthesis, structure and assessment of the cytotoxic properties of 2,5-dimethylazaferrocenyl phosphonates
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Synthesis, structure and assessment of the cytotoxic properties of 2,5-dimethylazaferrocenyl phosphonates

机译：2,5-二甲基氮杂二茂铁基膦酸酯的合成，结构和细胞毒性的评估

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摘要

The reaction of lithiated 2,5-dimethylazaferrocene 1 with diethyl chlorophosphate proceeds to give lateral and ring phosphonate products. The products 2 and 3 were characterized by spectroscopic (H-1, P-31{H-1} NMR, MS, IR) methods and 3 was treated with W(CO)(5)(thf) to form a crystalline W(CO)(5)-complex 4 which was characterized by single-crystal X-ray analysis. The new 2,5-dimethylazaferrocenyl phosphonates were transformed into the corresponding N-methyl iodide salts 5 and 6 in quantitative yields. Both salts are water soluble and stable compounds and an analysis of their cytotoxic and antiproliferative activity was carried out. Compound 6 possesses anti-metabolic activity which exhibited some preference towards the cancerous HeLa cell line over the non-cancerous NIH 3T3 cell line. These new compounds are the first examples of azaferrrocene (i.e. non-ferrocene) derivatives featuring biologically important phosphonate groups. The preliminary studies into cytotoxic activity indicates that as with ferrocene, azaferrocene can also be regarded as a potential source for organometallic anticancer agents, featuring the iron centre in the +2 oxidation state rather than the often utilized ferrocenium +3 species.
机译：锂化的2，5-二甲基氮杂二茂铁1与氯代磷酸二乙酯的反应进行，得到侧向和环状膦酸酯产物。产物2和3用光谱法（H-1，P-31 {H-1} NMR，MS，IR）表征，并用W（CO）（5）（thf）处理3形成结晶W（通过单晶X射线分析表征的CO）（5）-络合物4。将新的2，5-二甲基氮杂二茂铁基膦酸酯以定量收率转化成相应的N-甲基碘化物盐5和6。两种盐均为水溶性且稳定的化合物，并对其细胞毒性和抗增殖活性进行了分析。化合物6具有抗代谢活性，与非癌性NIH 3T3细胞系相比，其对癌性HeLa细胞系表现出一定的偏爱。这些新化合物是具有生物学重要膦酸酯基团的氮杂二茂铁（即非二茂铁）衍生物的第一个实例。对细胞毒性活性的初步研究表明，与二茂铁一样，氮杂二茂铁也可被视为有机金属抗癌剂的潜在来源，其铁中心呈+2氧化态，而不是经常使用的二茂铁fer。

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