Synthesis Of Chalcone Derivatives And Biological Activities

Chalcones are considered as the precursor of flavonoids and isoflavonoids in abundant plants. They consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon a,β-unsaturated carbonyl system chemically. Compounds containing chalcone moiety may enhance biological activity, due to its good flexibility. Two series of chalcone derivatives were synthesized, characterized, and evaluated their PTPIB inhibitory effects and anti-bacterial activity. Several compounds exhibited PTP1B inhibitory activity in the low micromole range. In the first series of 19 derivatives of (5-substitutedchalconyl-2,4-thiazolidinedione-3-yl)-methylbenzoic acid, compounds 8a,8b,8h,8k,8n and 8q exhibited significant activities with MIC values in the range of 0.5-4μg/mL against six Gram-positive bacteria (including the multidrug-resisitant clinical isolates), among which 8b showed the most potent PTPIB inhibitory activity with an IC50 of 0.56μM. All of these compounds did not exhibit any activities against Gram-negative bacteria (E. coli 1356 and E. coli 1682) at 64μg/mL. In the second series of 18 derivatives of N-(4-phenyl-thiazol-2-yl)-4-(substitutedchalconyl)benzaldehyde hydrazone, compound 13b showed the best PTP1B inhibitory effect with an IC50 of 2.57μM, and none of them exhibited any anti-bacterial activity at 64μg/mL.