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Molecular Modeling, Synthesis and Biological Evaluation of N-Phenyl-4-Hydroxy-6-Methyl-2-Quinolone-3-CarboxAmides as Anticancer Agents.

ABSTRACT: The emergence of phosphatidylinositol 3-kinase (PI3K?) in cancer development has accentuated its significance as a potential target for anticancer drug design. Twenty one derivatives of N-phenyl-4-hydroxy-6-methyl-2-quinolone-3-carboxamide were synthesized and characterized using NMR (1H and 13C) and HRMS. The derivatives displayed inhibitory activity against human epithelial colorectal adenocarcinoma (Caco-2) and human colon cancer (HCT-116) cell lines: compounds 8 (IC50 Caco-2 = 98 µM, IC50 HCT-116 = 337 µM) and 16 (IC50 Caco-2 = 13 µM, IC50 HCT-116 = 240.2 µM). Results showed that compound 16 significantly affected the gene encoding AKT, BAD, and PI3K. The induced-fit docking (IFD) studies against PI3K? demonstrated that the scaffold accommodates the kinase domains and forms H-bonds with significant binding residues.

SUBMITTER: Sabbah DA 

PROVIDER: S-EPMC7698136 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Molecular Modeling, Synthesis and Biological Evaluation of <i>N</i>-Phenyl-4-Hydroxy-6-Methyl-2-Quinolone-3-CarboxAmides as Anticancer Agents.

Sabbah Dima A DA   Hasan Shaima' E SE   Abu Khalaf Reema R   Bardaweel Sanaa K SK   Hajjo Rima R   Alqaisi Khalid M KM   Sweidan Kamal A KA   Al-Zuheiri Aya M AM  

Molecules (Basel, Switzerland) 20201116 22

The emergence of phosphatidylinositol 3-kinase (PI3Kα) in cancer development has accentuated its significance as a potential target for anticancer drug design. Twenty one derivatives of <i>N</i>-phenyl-4-hydroxy-6-methyl-2-quinolone-3-carboxamide were synthesized and characterized using NMR (<sup>1</sup>H and <sup>13</sup>C) and HRMS. The derivatives displayed inhibitory activity against human epithelial colorectal adenocarcinoma (Caco-2) and human colon cancer (HCT-116) cell lines: compounds <b  ...[more]

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