Synthesis of novel flavanone derivatives and their anti Staphylococcus aureus evaluation

Abstract

The authors synthesized two novel flavanones bearing iso-pentenyl side chain and evaluated their anti Staphylococcus aureus(S. aureus) activity. The target compounds 7a[2-5′-(1″,2″-dimethylallyl)-2′-methoxy-4′,5,7-tetrahydroxyflavanone] and 7b[2-5′-(1″,2″-dimethylallyl)-3′-methoxy-4′,5,7-tetrahydroxyflavanone]_were synthesized respectively through total four steps starting from 2,4,6-trihydroxy acetophenone(3) and the corresponding iso-pentenyl substituted benzaldehyde(1), in which the 1,2-dimethyl-2-propenyl group had been introduced previously via abnormal Claisen rearrangement. The bioactivities of the two flavanones against S. aureus strains ATCC 25923, 29213, and MRSA 252 were evaluated, showing the same minimum inhibitory concentration(MIC) value of 16 μg/mL.

Keywords

Flavanone / Abnormal Claisen rearrangement / Antimicrobial / iso-Pentenyl side chain

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