<br/>A specific retinoid against methicillin-resistant Staphylococcus aureus (MRSA), known as CD437, has piqued our interest and led to the development of a range of analogs, some of which have demonstrated significant activity against gram-positive pathogens in past research. Our best performing compound, analog 2, has also shown a high affinity for retinoid-binding proteins with a concentration-dependent relationship and a low solubility in serum. These factors force us to question the therapeutic viability of these compounds but have also brought us to the consideration of isosteric substitutions within the scaffold of the molecule to circumvent these issues. We proposed a new class of analogs incorporating an azaborine substitution in place of the naphthalene moiety. Azaborines have a nitrogen-boron bond in place of a carbon–carbon double bond which alters the electronics of the parent scaffold and has been explored successfully in cancer research. Using this information, our desired analogs integrating the desired isometric substitution were synthesized and their antimicrobial activity was measured and documented.

Exploration into the synthesis and evaluation of an antibacterial azaborine retinoid isostere

ACS Fall 2021

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