Piano Stool Aminoalkylidene‐Ferracyclopentenone Complexes from Bimetallic Precursors: Synthesis and Cytotoxicity Data

Rocco Dalila; Batchelor Lucinda K.; Ferretti Eleonora; Zacchini Stefano; Pampaloni Guido; Dyson Paul J.; Marchetti Fabio

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Piano Stool Aminoalkylidene‐Ferracyclopentenone Complexes from Bimetallic Precursors: Synthesis and Cytotoxicity Data

机译：钢琴凳氨基烷基苯甲酯 - 铁键蛋白烯酮来自双金属前体的复合物：合成和细胞毒性数据

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Abstract The reaction of pyrrolidine with a series of cationic diiron cyclopentadienyl complexes containing a bridging vinyliminium ligand gives access to piano stool monoiron complexes based on a five‐membered metallacycle that includes a vinyl‐aminoalkylidene moiety, in moderate to high yields. The resulting metallacyclic motif (aminoalkylidene‐ferracyclopentenone) is unique in organometallic chemistry and is partially pre‐constructed on the dinuclear frame. The monoiron products were fully characterized by elemental analysis, IR and multinuclear NMR spectroscopy, and in a number of cases by X‐ray diffraction and cyclic voltammetry. They are robust in aqueous solutions and generally unreactive towards alkylating agents in organic solvents. However, a cationic derivative was prepared in high yield by methylation of a 2‐pyridyl group. The cytotoxicity of both neutral and ionic complexes was assessed on cancerous (A2780 and A280cisR) and non‐cancerous (HEK293) cell lines, revealing the influence of local structural modifications on the antiproliferative activity and the selectivity of the compounds.

机译：摘要吡咯烷与一系列阳离子二酮环戊二烯基络合物的反应，含有桥接乙烯基尼鎓配体，可基于包含乙烯基 - 氨基烷基部分的五元金属核，中等至高产率进入钢琴粪便单铁络合物。得到的金属谱基序（氨基烷基 - 铁氰基酮）在有机金属化学中是独一无二的，并且在二核框架上部分预构建。通过元素分析，IR和多核NMR光谱，单对肌号产品完全表征，并在多种情况下通过X射线衍射和循环伏安法。它们在水溶液中具有稳健，并且通常在有机溶剂中对烷基化剂不能反应。然而，通过2-吡啶基的甲基化制备阳离子衍生物。在癌症（A2780和A280CISR）和非癌变（HEK293）细胞系中评估中性和离子复合物的细胞毒性，揭示了局部结构修饰对抗增殖活性和化合物的选择性的影响。

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《ChemPlusChem》 |2020年第1期|共13页
作者
Rocco Dalila; Batchelor Lucinda K.; Ferretti Eleonora; Zacchini Stefano; Pampaloni Guido; Dyson Paul J.; Marchetti Fabio;
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作者单位

Dipartimento di Chimica e Chimica IndustrialeUniversità di PisaVia G. Moruzzi 13 56124 Pisa Italy;

Institut des Sciences et Ingénierie ChimiquesEcole Polytechnique Fédérale de Lausanne (EPFL)CH-1015;

Institut für Anorganische ChemieTammannstr. 4 37077 G?ttingen Germany;

Dipartimento di Chimica Industriale “Toso Montanari”Università di BolognaViale Risorgimento 4 40136;

Dipartimento di Chimica e Chimica IndustrialeUniversità di PisaVia G. Moruzzi 13 56124 Pisa Italy;

Institut des Sciences et Ingénierie ChimiquesEcole Polytechnique Fédérale de Lausanne (EPFL)CH-1015;

Dipartimento di Chimica e Chimica IndustrialeUniversità di PisaVia G. Moruzzi 13 56124 Pisa Italy;

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原文格式 PDF
正文语种 eng
中图分类化学;
关键词
cytotoxicity; iron; metal-based drugs; piano stool complexes; vinyliminium ligands;

机译：细胞毒性;铁;基于金属的药物;钢琴凳子络合物;乙烯基鎓配体;

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专利

1. Piano Stool Aminoalkylidene‐Ferracyclopentenone Complexes from Bimetallic Precursors: Synthesis and Cytotoxicity Data [J] . Rocco Dalila, Batchelor Lucinda K., Ferretti Eleonora, ChemPlusChem . 2020,第1期

机译：钢琴凳氨基烷基苯甲酯 - 铁键蛋白烯酮来自双金属前体的复合物：合成和细胞毒性数据
2. BIMETALLIC COMPLEXES WITH CHIRAL MOLYBDENUM CENTERS AND BIS(ETA-5-CYCLOPENTADIENYL) BRIDGES - INTERCHANGE BETWEEN LEGS IN THREE-LEGGED PIANO STOOL COMPLEXES [J] . Galakhov MV., Dejesus E., Royo P., Organometallics . 1995,第8期

机译：具有手性钼中心和双（ETA-5-环戊二烯基）桥的双金属配合物-三足的PIANO STOOL配合物中的腿之间的互换
3. Cytotoxicity of Ru(II) piano-stool complexes with chloroquine and chelating ligands against breast and lung tumor cells: Interactions with DNA and BSA [J] . Colina-Vegas Legna, Villarreal Wilmer, Navarro Maribel, Journal of Inorganic Biochemistry: An Interdisciplinary Journal . 2015,第Null期

机译：Ru（II）琴凳配合物与氯喹和螯合配体对乳腺和肺部肿瘤细胞的细胞毒性：与DNA和BSA的相互作用
4. ELECTROCHEMICAL SYNTHESIS OF VOLATILE METAL COMPLEXES, AS PRECURSORS FOR FUNCTIONAL MATERIAL SYNTHESIS BY THE CVD METHOD [C] . Y.A. MAZURENKO, A.I. GERASIMCHUK, NATO NATO advanced research workshop on green industrial applications of ionic liquids . 2002

机译：挥发性金属配合物的电化学合成，作为CVD法合成功能材料的前体
5. Activation of Propargylic Alcohols by Piano-Stool Ruthenium Complexes Bearing Phosphoramidite Ligands. [D] . Costin, Stephen. 2010

机译：带有亚磷酰胺配体的钢琴凳钌配合物活化丙炔醇。
6. Iridium piano stool complexes with activity against S. aureus and MRSA: it is past time to truly think outside of the box [O] . Christine M. DuChane, George W. Karpin, Marion Ehrich, 2019

机译：铱合金钢琴凳子配合物对金黄色葡萄球菌和MRSA具有活性：真正思考是过去的时机
7. Cytotoxicity of ruthenium(II) piano-stool complexes with imidazole-based PN ligands [O] . Huber, Wilhelm, Broehler, Philip, Waetjen, Wim, 2012

机译：咪唑基PN配体的钌（II）钢琴凳配合物的细胞毒性
8. Homo- and Hetero-Bimetallic Mu(Eta1-O:Eta1-O') Formate Complexes (M-OCHO-M')+PF6-(M,M'=(Eta5-C5H5)(CO)(NO)Re, (Eta5-C5H5)(CO)3W, and (Eta5-C5H5)(CO)2Fe): Their Synthesis, Solution Lability, and Reactivity Towards Hydride Donors [R] . Tso, C. C., Cutler, A. R. 1988

机译：同型和异型双金属mu（Eta1-O：Eta1-O'）甲酸盐配合物（m-OCHO-m'）+ pF6-（m，m'=（Eta5-C5H5）（CO）（NO）Re，（ Eta5-C5H5）（CO）3W和（Eta5-C5H5）（CO）2Fe）：它们的合成，溶液稳定性和对氢化物供体的反应性

Piano Stool Aminoalkylidene‐Ferracyclopentenone Complexes from Bimetallic Precursors: Synthesis and Cytotoxicity Data

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