School of Chemistry and Environment, South China Normal University, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, Guangzhou 510006, P. R. China.
College of Sports and Rehabilitation, Gannan Medical University, Ganzhou, Jiangxi province 341000, P. R. China.
Org Biomol Chem. 2019 May 28;17(20):5138-5147. doi: 10.1039/c9ob00736a. Epub 2019 May 10.
A series of amino acid derivatives are successfully synthesized via a metal-free C-N coupling reaction of 5-alkoxy-3,4-dihalo-2(5H)-furanones and amino acids. Their structures are well characterized with H NMR, C NMR, ESI-MS and elemental analysis. As potential linkers of the 2(5H)-furanone unit with other drug moieties containing a hydroxyl or amino group, the effect of amino acids is investigated by comparison with other 2(5H)-furanone compounds by constructing C-O/C-S bonds. The preliminary results of the biological activity assay by the MTT method on a series of cancer cell lines in vitro reveal that the introduction of amino acids basically has no toxic effect. This can lead to these 2(5H)-furanone derivatives being further well-linked with other bioactive moieties with amino or hydroxy groups as expected. Thus, the biological activity assay gives a direction for the design of bioactive 2(5H)-furanones based on these amino acid linkers.
通过 5-烷氧基-3,4-二卤-2(5H)-呋喃酮和氨基酸的无金属 C-N 偶联反应，成功合成了一系列氨基酸衍生物。它们的结构通过 1H NMR、13C NMR、ESI-MS 和元素分析得到了很好的表征。作为将呋喃酮单元与含有羟基或氨基的其他药物部分连接的潜在连接子，通过构建 C-O/C-S 键，与其他 2(5H)-呋喃酮化合物进行比较，研究了氨基酸的影响。通过 MTT 法在体外一系列癌细胞系上进行的生物活性测定的初步结果表明，氨基酸的引入基本上没有毒性作用。这可以导致这些 2(5H)-呋喃酮衍生物与其他具有氨基或羟基的生物活性部分进一步很好地连接，正如预期的那样。因此，生物活性测定为基于这些氨基酸连接子设计生物活性 2(5H)-呋喃酮提供了方向。
