The Suzuki–Miyaura coupling is one of the ubiquitous method for the carbon–carbon bond-forming reactions in organic chemistry. Its popularity is due to its ability to undergo extensive coupling reactions to generate a broad range of biaryl motifs in a straightforward manner displaying a high level of functional group tolerance. A convenient and efficient synthetic route to arylate different substituted flavonols through the Suzuki–Miyaura cross-coupling reaction has been explained in this study. The arylated products were acquired by the coupling of a variety of aryl boronic acids with flavonols under Pd(OAc)₂ catalyzed reaction conditions in a ligand-free reaction strategy. Subsequently, the antibiofilm and antivirulence properties of the arylated flavonols against Pseudomonas aeruginosa PAO1 were studied thoroughly. The best ligands for quorum sensing proteins LasR, RhlR, and PqsR were identified using molecular docking study. These best fitting ligands were then studied for their impact on gene expression level of P. aeruginosa by RT-PCR towards quorum sensing genes lasB, rhlA, and pqsE. The downregulation in the gene expression with the effect of synthesized flavonols endorse the antibiofilm efficiency of the compounds.

中文翻译：

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钯催化无配体 Suzuki-Miyaura 偶联产生的黄酮醇类似物抗铜绿假单胞菌 PAO1 的抗生物膜和抗毒特性的合成和研究

铃木-宫浦偶联是有机化学中普遍存在的碳-碳键形成反应方法之一。它的受欢迎是因为它能够进行广泛的偶联反应，以直接的方式生成广泛的联芳基序，显示出高水平的官能团耐受性。本研究解释了通过铃木-宫浦交叉偶联反应芳基化不同取代黄酮醇的便捷有效的合成路线。在Pd(OAc) ₂催化反应条件下，采用无配体反应策略，将多种芳基硼酸与黄酮醇偶联，得到芳基化产物。随后，深入研究了芳基化黄酮醇对铜绿假单胞菌PAO1 的抗生物膜和抗毒力特性。使用分子对接研究鉴定了群体感应蛋白 LasR、RhlR 和 PqsR 的最佳配体。然后通过针对群体感应基因lasB、rhlA和pqsE的 RT-PCR研究这些最合适的配体对铜绿假单胞菌基因表达水平的影响。合成黄酮醇的作用导致基因表达下调，证实了该化合物的抗生物膜效率。