Our Laboratory has conducted an in-depth investigation of the relatively unknown class of 2-acyl-1-hydroxy-2,3,1-benzodiazaborinines and similar ring-fused boron heterocycles of interest as potential antibacterial agents.  Details of the synthesis, characterization (NMR, X-ray, etc.), and biological activity of more than thirty compounds will be presented.  Many of these targets were found to exist in one of three sometimes interconvertable structural forms along a dehydration continuum of open hydrazone, monomeric B-hydroxy diazaborine, and symmetrical anhydro dimer species.  By X-ray, the anhydro dimers were shown to have an unprecedented structure featuring a double intramolecular O?B chelation.  The crystal structure of another target revealed it to be the first member of a new class of pentacyclic boron heterocycles, while that of still another showed it to be the zwitterionic outcome of an unanticipated intramolecular N?B chelation.  Of the targets tested, nine were found active against E. coli, and two were active against M. smegmatis.  The structural similarity between the latter two suggests a possible basis for their activity.

Synthesis, structural variability, and biological activity of ring-fused 2-acyl-1-hydroxy-2,3,1-diazaborinine heterocycles

248th National Meeting (2014)

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