Lijun Liu, Adam J. V. Marwitz, B. Matthews
Sep 1, 2009
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Angewandte Chemie
Abstract
The element boron has not received much attention in biomedical applications compared to its periodic table neighbors carbon, nitrogen and oxygen. Arguably, this might be due to the apparent “insignificance” of boron in Nature’s evolution of life.[1,2] Boron has however useful elemental and chemical features that include nuclear spin, large cross section for neutron capture, and Lewis acidity. If boron could be incorporated into biologically relevant molecules[3] it might benefit biomedical research by being used as a marker,[4] as a new pharmacophore,[5] or in cancer therapy.[6] We are interested in synthetic approaches that will allow the incorporation of boron into such molecules[7] with minimal perturbation of their structures. 1,2-Dihydro-1,2-azaborines (abbreviated as 1,2-azaborines) serve as a unique structural platform to accomplish this goal because of their isostructural relationship with arenes, a ubiquitous motif in living organisms and in pharmaceuticals. Furthermore, the bonding of arenes with cations and other arenes through cation-π[8] and π-π[9] interactions have been demonstrated to be vital in biological systems. Thus, the broad utility and fundamental importance of arenes in biomedical research combined with the unique elemental/chemical features of boron, and the potential of expanding the diversity of arene structures through CC/BN isosterism[10] make 1,2-azaborines attractive targets for biomedical investigation (Scheme 1).