Insights on a new sulfonamide chalcone with potential antineoplastic application

• Published in: Journal of molecular modeling Vol. 27; no. 7; p. 211
• Main Authors: Wenceslau, Patricia R. S., de Paula, Renata L. G., Duarte, Vitor S., D’Oliveira, Giulio D. C., Guimarães, Laura M. M., Pérez, Caridad N., Borges, Leonardo L., Martins, José L. R., Fajemiroye, James O., Franco, Chris H. J., Perjesi, Pal, Napolitano, Hamilton B.
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer Berlin Heidelberg 01-07-2021; Springer Nature B.V
• Subjects: Binding sites; Characterization and Evaluation of Materials; Chemistry; Chemistry and Materials Science; Computer Appl. in Life Sciences; Computer Applications in Chemistry; Flavonoids; Ligands; Molecular Medicine; Natural products; Original Paper; Stability analysis; Sulfonamides; Theoretical and Computational Chemistry; VIII Symposium on Electronic Structure and Molecular Dynamics – VIII SeedMol; Sulfonamide chalcone; X-ray diffraction; M06-2X/6–311++G(d,p); experiments
• ISSN: 1610-2940; 0948-5023
• DOI: 10.1007/s00894-021-04818-w

Chalcones (E)-1,3-diphenyl-2-propene-1-ones, a class of biosynthetic precursor molecules of flavonoids, have a wide variety of biological applications. Besides the natural products, many synthetic derivatives and analogs became an object of continued interest in academia and industry. In this work, a synthesis and an extensive structural study were performed on a sulfonamide chalcone 1-Benzenesulfonyl-3-(4-bromobenzylidene)-2-(2-chlorophenyl)-2,3-dihydro-1H-quinolin-4-one with potential antineoplastic application. In addition,
in silico
experiments have shown that the sulfonamide chalcone fits well in the ligand-binding site of EGFR with seven μ-alkyl binding energy interactions on the ligand-binding site. Finally, the kinetic stability and the pharmacophoric analysis for EGFR indicated the necessary spatial characteristics for potential activity of sulfonamide chalcone as an antagonist.