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首页> 外文期刊>New Journal of Chemistry >Bis-maltol-polyamine family: structural modifications at strategic positions. Synthesis, coordination and antineoplastic activity of two new ligands
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Bis-maltol-polyamine family: structural modifications at strategic positions. Synthesis, coordination and antineoplastic activity of two new ligands

机译：BIS-MALTOL-多胺家族：战略位置的结构修改。 两种新配体的合成，协调和抗血压活性

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摘要

Two new maltol-based ligands are presented, L1 (N,N '-bis((3-hydroxy-6-methyl-4-pyron-2-yl)methyl)-N,N '-dimethylethylenediamine) and L2 (N,N '-bis((3-hydroxy-6-hydroxymethyl-4-pyron-2-yl)methyl)-N,N '-dimethylethylenediamine). They were strategically designed by inserting a methyl or hydroxymethyl function at C6, to study the previously hypothesized involvement of that ring position in the anticancer properties and the peculiar metal coordination ability in aqueous solution already shown by this family of ligands. Solid state and solution studies revealed differences neither in the molecular conformation or crystal packing nor in the acid-base behavior compared with the precursor Malten. The introduced substituent groups seem to affect instead both the degradation time (ca. 4-5 h for L1 and L2vs. 10 h for Malten) and the binding properties towards Cu(ii), Zn(ii) and Co(ii), log K values being the highest for L1 within the series of the diamino-bis-maltol ligands. The introduction of -CH2OH at C6 is sufficient to impair the biological activity of the compound and is coherent with the hypothesized mechanism of action.
机译：提出了两种新的麦芽醇基配体，L1（N，N’-双（（3-羟基-6-甲基-4-吡喃-2-基）甲基）-N，N’-二甲基乙二胺）和L2（N，N’-双（（3-羟基-6-羟基甲基-4-吡喃-2-基）甲基）-N，N’-二甲基乙二胺）。通过在C6处插入甲基或羟甲基功能，对其进行策略性设计，以研究之前假设的该环位置与抗癌性质的关系，以及该配体家族已经显示的水溶液中特殊的金属配位能力。固态和溶液研究表明，与前体麦芽糖相比，其分子构象或晶体堆积以及酸碱行为均不存在差异。引入的取代基似乎会影响降解时间（L1和L2的降解时间分别为4-5小时和10小时），以及对Cu（ii）、Zn（ii）和Co（ii）的结合性能，在二氨基双麦芽醇配体系列中，L1的对数K值最高。在C6处引入-CH2OH足以损害化合物的生物活性，并且与假设的作用机制一致。

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  • 来源
    《New Journal of Chemistry》 |2021年第5期|共11页
  • 作者

    Giorgi Luca; Ambrosi Gianluca; Paderni Daniele; Conti Luca; Amatori Stefano; Romagnoli Francesca; Rossi Patrizia; Formica Mauro; Macedi Eleonora; Giorgi Claudia; Paoli Paola; Fanelli Mirco; Fusi Vieri;

  • 作者单位

    Univ Urbino Carlo Bo Dipartimento Sci Pure &

    Applicate Via Stn 4 I-161029 Urbino Italy;

    Univ Urbino Carlo Bo Dipartimento Sci Pure &

    Applicate Via Stn 4 I-161029 Urbino Italy;

    Univ Urbino Carlo Bo Dipartimento Sci Pure &

    Applicate Via Stn 4 I-161029 Urbino Italy;

    Univ Florence Dept Chem Ugo Schiff Via Lastruccia 3-13 I-50019 Sesta Fiorentino Italy;

    Univ Urbino Carlo Bo Dept Biomol Sci Mol Pathol Lab PaoLa Via Arco Augusto 2 I-61032 Fano Italy;

    Univ Urbino Carlo Bo Dipartimento Sci Pure &

    Applicate Via Stn 4 I-161029 Urbino Italy;

    Univ Florence Dept Ind Engn Via S Marta 3 I-50139 Florence Italy;

    Univ Urbino Carlo Bo Dipartimento Sci Pure &

    Applicate Via Stn 4 I-161029 Urbino Italy;

    Univ Urbino Carlo Bo Dipartimento Sci Pure &

    Applicate Via Stn 4 I-161029 Urbino Italy;

    Univ Florence Dept Chem Ugo Schiff Via Lastruccia 3-13 I-50019 Sesta Fiorentino Italy;

    Univ Florence Dept Ind Engn Via S Marta 3 I-50139 Florence Italy;

    Univ Urbino Carlo Bo Dept Biomol Sci Mol Pathol Lab PaoLa Via Arco Augusto 2 I-61032 Fano Italy;

    Univ Urbino Carlo Bo Dipartimento Sci Pure &

    Applicate Via Stn 4 I-161029 Urbino Italy;

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