Antibacterial and antioxidant activity evaluation of novel symmetrical and unsymmetrical C 5-curcuminoids

Curcumin remains one of the most widely studied natural product due to its wide range of biological activities but because of the presence of central β-diketone unit which is responsible for its poor bioavailability, this molecule cannot be developed as a drug. In order to overcome this, curcumin has been modified to metabolically stable symmetrical and unsymmetrical C5-curcuminoids and their in vitro antibacterial and antioxidant activity were studied. Few of the synthesized C5-curcuminoids (10, 11 and 25) displayed excellent potency (MIC value 1.5 to 6.25 μg/mL) against the tested bacterial strains. Six of the analogues (10, 12-15 and 25) were also found to exhibit good antioxidant activity (IC50 values 33.87 to 49.45 μg/mL) in a DPPH free radical scavenging assay. The test compounds have been further subjected to in silico ADMET analysis and various pharmacokinetic properties were calculated. Compounds 20, 23-25 are predicted to have less toxic effects and follow the permissible pharmacokinetic criterion.