Synthesis and antimicrobial screening of some quinonoid systems

Abstract

A new general synthetic strategy for the synthesis of benzo[c]pyranquinones, with a view to making the route more generally applicable to the synthesis of naturally occurring naphtho[2,3-c]pyranquinones of potential importance as antimicrobial agents, has been developed. This synthetic approach afforded, inter alia, the natural products, is oeleutherin and hongconin (as their racemates) in good overall yield. A new high-yielding synthetic route for the synthesis of 1,5-dimethoxy-4naphthol, 2-allyl-5-methoxy-I,4-naphthoquinone and 3-acetyl-5-methoxy-I,4naphthoquinone, all ofwhich are key intermediates in several laboratory routes to naturally occurring naphtho[2,3-c]pyranquinones, has also been developed. A key-step in their formation is respective methylation, allylation or acetylation of a common intermediate Diels-Alder adduct. A feasible route to a naphtho[2,3-c]pyranone was developed. This model route is envisaged to be generally applicable for the synthesis of higher oxygenated naphtho[2,3-c]pyranones by virtue ofthe nature of the conditions and reagents used in this synthetic route. The target quinones and some of their precursors were evaluated for antimicrobial activity and specificity in vitro. This showed that the benzo[c]pyranquinones have a broader specificity spectrum than their naphtho[2,3-c] or naphtho[2,3-b] analogues.