Compounds synthesized from carbohydrate substrates have yielded promising lead molecules for pharmaceutical developments, as many are approved for the clinical management of a wide range of diseases. Among them, thiourea moieties are the gold mines of antibacterial molecules. In view of the lack and need for new antibiotics, a series of 16 D-fructose-based thiourea compounds were synthesized from asymmetric aldol reaction and isopropylidenation. The new compounds were established from nuclear magnetic resonance, Fourier-transform infrared, and electrospray ionization mass spectrometry. Using disk diffusion assay for antibiotic susceptibility, four of the novel compounds were found to have concentration-dependent antibacterial activities. The addition of trifluoromethyl groups at the meta-position on the phenyl ring of the thioureas appeared to promote bacterial inhibitory action. Thiourea 2a exhibited the most potent activity against the Gram-negative species, Klebsiella pneumoniae, Escherichia coli, and Salmonella typhi, as well as the Gram-positive species, Micrococcus luteus; but not against all bacteria tested. Thiourea 2b and 3a had lower efficacy but showed better broad-spectrum activity against most bacteria tested. Thiourea 3b displayed species-specific activity only against K. pneumoniae and S. typhi. Our findings show the benefits and prospects of synthesizing new carbohydrate compounds for therapeutic medication.
Lalhmangaihzuala S, Laldinpuii ZT, Lalthanpuii PB, Pachuau Z, Vanlaldinpuia K, Lalchhandama K. Screening of novel carbohydrate-derived thioureas for antibacterial activity. J Appl Pharm Sci. 2024. Online First. http://doi.org/10.7324/JAPS.2024.180485
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