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Design, Synthesis, and Antifungal Activity of 3-Substituted-2(5H)-Oxaboroles.

ABSTRACT: Next generation antimicrobial therapeutics are desperately needed as new pathogens with multiple resistance mechanisms continually emerge. Two oxaboroles, tavaborole and crisaborole, were recently approved as topical treatments for onychomycosis and atopic dermatitis, respectively, warranting further studies into this privileged structural class. Herein, we report the antimicrobial properties of 3-substituted-2(5H)-oxaboroles, an unstudied family of medicinally relevant oxaboroles. Our results revealed minimum inhibitory concentrations as low as 6.25 and 5.20 μg/mL against fungal (e.g., Penicillium chrysogenum) and yeast (Saccharomyces cerevisiae) pathogens, respectively. These oxaboroles were nonhemolytic and nontoxic to rat myoblast cells (H9c2). Structure-activity relationship studies suggest that planarity is important for antimicrobial activity, possibly due to the effects of extended conjugation between the oxaborole and benzene rings.

SUBMITTER: Campbell R 

PROVIDER: S-EPMC10945556 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature

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Design, Synthesis, and Antifungal Activity of 3-Substituted-2(<i>5H</i>)-Oxaboroles.

Campbell Rose R   Buchbinder Nicklas W NW   Szwetkowski Connor C   Zhu Yumeng Y   Piedl Karla K   Truong Mindy M   Matson John B JB   Santos Webster L WL   Mevers Emily E  

ACS medicinal chemistry letters 20240222 3

Next generation antimicrobial therapeutics are desperately needed as new pathogens with multiple resistance mechanisms continually emerge. Two oxaboroles, tavaborole and crisaborole, were recently approved as topical treatments for onychomycosis and atopic dermatitis, respectively, warranting further studies into this privileged structural class. Herein, we report the antimicrobial properties of 3-substituted-2(<i>5H</i>)-oxaboroles, an unstudied family of medicinally relevant oxaboroles. Our re  ...[more]

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