article · Organic & Biomolecular Chemistry
Screening of a diverse chemical library identified a specific 2-thioxodihydropyrido[2,3-d]pyrimidine compound, designated 10a, showing broad-spectrum antibacterial potency and antifungal properties. Researchers established a rapid synthetic method for 10a using microwave irradiation, dimethylformamide, and an iodine catalyst, reducing reaction time from 15 hours under traditional heating to 30 minutes. Pharmacokinetic evaluations and drug-likeness calculations indicated promising drug-like characteristics for the molecule. Building on these results, a series of seven related compounds was synthesised. These variants demonstrated broad antimicrobial activity with minimum inhibitory concentrations between 0.49 and 7.81 micrograms per millilitre, alongside selectivity indices exceeding 5.6 against normal human colon cells. Furthermore, the derivative molecules exhibited moderate to strong antifungal actions with minimum inhibitory concentrations ranging from 1.95 to 15.63 micrograms per millilitre.
Identifying effective antimicrobial candidates is critical for developing new therapies against infectious diseases. Establishing an efficient synthetic pathway that dramatically reduces production time from 15 hours to 30 minutes, alongside demonstrating potent antibacterial and antifungal activity with favourable selectivity over healthy human colon cells, offers valuable early insights for antimicrobial drug discovery pipelines.
This work could inform the discovery and production of new synthetic antibacterial and antifungal agents. Pharmaceutical companies and medicinal chemistry researchers are the most relevant prospective users. The findings represent early-stage laboratory research, with efficacy and selectivity demonstrated solely in vitro against cell cultures and microbial strains, meaning extensive further testing is required before reaching clinical or commercial application.
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The screening of a small library of diverse chemical structures resulted in the identification of 2-thioxodihydropyrido[2,3-d]pyrimidine 10a as having broad spectrum antibacterial activity (MIC 0.49-3.9 μg mL-1), and reasonable antifungal activity (MIC 31.25 μg mL-1). An expeditious synthesis of 10a was optimized by varying solvents, catalysts and the use of microwave irradiation with the best conditions using DMF as a solvent, I2 (10 mol%) and a 30 minutes reaction time compared to 15 h for classic conventional heating. The pharmacokinetic properties and calculation of drug likeness of 10a suggested good traditional drug-like properties and led to the synthesis of a small library with seven compounds 10a and 10d-i showing broad antimicrobial activity (MIC = 0.49-7.81 μg mL-1) and selectivity indices of more than 5.6 against the normal colon cell line (CCD-33Co). The antifungal activity of compounds 10d-i was moderate to strong with MIC values of 1.95-15.63 μg mL-1.
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DOI: 10.1039/c8ob00627j
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