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

Abstract

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.