Benny Anjitha Theres, Thamim Masthan, Srivastava Prakhar, Suresh Sindoora, Thirumoorthy Krishnan, Rangasamy Loganathan, S Karthikeyan, Easwaran Nalini, Radhakrishnan Ethiraj Kannatt
Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology Vellore-632014 India
Department of Pharmacy, The Ohio State University USA.
RSC Adv. 2024 Apr 16;14(18):12278-12293. doi: 10.1039/d3ra08617h.
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) catalyzed reaction conditions in a ligand-free reaction strategy. Subsequently, the antibiofilm and antivirulence properties of the arylated flavonols against 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 by RT-PCR towards quorum sensing genes , , and . The downregulation in the gene expression with the effect of synthesized flavonols endorse the antibiofilm efficiency of the compounds.
铃木-宫浦偶联反应是有机化学中碳-碳键形成反应中普遍使用的方法之一。它之所以广受欢迎，是因为它能够进行广泛的偶联反应，以直接的方式生成各种联芳基结构，且对官能团具有较高的耐受性。本研究阐述了一条通过铃木-宫浦交叉偶联反应芳基化不同取代黄酮醇的便捷高效合成路线。在无配体反应策略下，在Pd(OAc)催化反应条件下，通过多种芳基硼酸与黄酮醇的偶联反应得到芳基化产物。随后，深入研究了芳基化黄酮醇对PAO1的抗生物膜和抗毒力特性。通过分子对接研究确定了群体感应蛋白LasR、RhlR和PqsR的最佳配体。然后通过RT-PCR研究这些最佳拟合配体对群体感应基因lasI、rhlI和pqsA基因表达水平的影响。合成黄酮醇作用下基因表达的下调证实了这些化合物的抗生物膜效率。
