Synthesis, characterization, docking study and antiviral evaluation of new 3,5-Bis(benzylidene)piperidin-4-one Derivatives bearing phosphonate group

Eight new 3,5-bis(benzylidene)piperidin-4-one derivatives bearing phosphonate group were synthesized rapidly in two step via microwave irradiation of aldehydes and 4-piperdinone in water catalyzed by potassium carbonate. This method is efficient, easy, and green with excellent yield of 3,5-bis(benzylidene)piperidin-4-one derivatives bearing phosphonate group. These products were characterized via their 1H, 13C, 31P NMR and mass analyses. Molecular docking studies on these highly potent substances were verified. The choice of certain compounds (4b, 4 g, and 4 h) according to their high activity with the above antiviral Common Cold organism was taken from the Protein Data Bank (PDB). Compound 4b is more active than compounds 4h and 4g, as a results of compound 4b made more bonds with amino acid of protein than compounds 4h and 4g These compounds display potent antiviral activity against a common respiratory virus (RV) infections. Moderate anti-RV infections with reductions in virus titers ranging from 1 to 2 log10 TCID50 were observed from 3a,d, and 4a,d compounds. Strong anti-RV activities with a reduction in virus titers ˃ 2 log10 TCID50 were observed from compounds 3b, 3 g, 3 h, and compounds 4b, 4 g, and 4h Structure Activity relationship showed strong activity that has been detected by replacing the p-position with the fluoro group (3b and 4b), the phenyl moiety with furyl (3g and 4g), or theinyl (3h and 4h) moieties