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Combinatorial Synthesis and Antibacterial Evaluation of an Indexed Chalcone Library

A 120‐membered chalcone library has been designed and prepared from six differently substituted acetophenones (A1–A6) and 20 benzaldehydes (B1–B20). The library was subjected to biological studies targeted against six bacterial strains. For the identification of the most‐active member(s) of the library, the so‐called indexed or positional‐scanning method was applied. Six out of 26 sub‐libraries, i.e., AL1 – AL6, were synthesized by keeping the acetophenone moiety A fixed and using equimolar quantities of the 20 different benzaldehydes. The remaining 20 sub‐libraries BL1 – BL20 were prepared by keeping the benzaldehyde B component fixed and varying the six acetophenones (Table 1). The bactericidal activities of the resulting sub‐libraries were tested and used as indices to the rows or columns of a two‐dimensional matrix. Finally, parallel synthesis of 24 specific members with the highest‐expected antibacterial activities, present in two sub‐libraries, was carried out. These chalcones were screened again, and the results were exploited for establishing the structure–activity relationship (SAR) and the identification of the lead compound, which turned out to be 1,3‐bis(2‐hydroxyphenyl)prop‐2‐en‐1‐one (A2B2) in terms of activity towards Staphylococcus aureus and Bacillus subtilis (Tables 5–7).