Synthesis of 6,12-Methanobenzo[d]pyrano[3,4-g][1,3]dioxocin-1(12H)-ones and Study of Their Interaction with DNA and β-Lactoglobulin.

An efficient synthesis of 6,12-methanobenzo[d]pyrano[ 3,4-g][1,3]dioxocin-1(12H)-ones, a new class of 2,8-dioxabicyclo[ 3.3.1]nonanes, starting from 2-hydroxychalcones or their analogues and 4-hydroxy-6-methyl-2H-pyran-2-one has been achieved by use of amberlyst-15, a sulfonated polystyrene resin, as a recyclable heterogeneous catalyst. The methodology involves a domino sequence of Michael addition and two-stage heterocyclization. Among the synthesized products, two show significant ct-DNA-binding properties and all show strong binding with the carrier protein β-lactoglobulin (β-lg). A study of antibacterial properties conducted on two bacterial species by using four compounds showed that two of them are moderately active. [ABSTRACT FROM AUTHOR]