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Synthesis of Novel Triazine-Based Chalcones and 8,9-dihydro-7 H -pyrimido[4,5- b ][1,4]diazepines as Potential Leads in the Search of Anticancer, Antibacterial and Antifungal Agents.
International Journal of Molecular Sciences 2024 March 23
This study presents the synthesis of four series of novel hybrid chalcones ( 20,21 ) a - g and ( 23,24 ) a - g and six series of 1,3,5-triazine-based pyrimido[4,5- b ][1,4]diazepines ( 28 - 33 ) a - g and the evaluation of their anticancer, antibacterial, antifungal, and cytotoxic properties. Chalcones 20b , d , 21a,b , d , 23a , d - g , 24a - g and the pyrimido[4,5- b ][1,4]diazepines 29e , g , 30g , 31a , b , e - g , 33a , b , e - g exhibited outstanding anticancer activity against a panel of 60 cancer cell lines with GI50 values between 0.01 and 100 μM and LC50 values in the range of 4.09 μM to >100 μM, several of such derivatives showing higher activity than the standard drug 5-fluorouracil (5-FU). On the other hand, among the synthesized compounds, the best antibacterial properties against N. gonorrhoeae , S. aureus (ATCC 43300), and M. tuberculosis were exhibited by the pyrimido[4,5- b ][1,4]diazepines (MICs: 0.25-62.5 µg/mL). The antifungal activity studies showed that triazinylamino-chalcone 29e and triazinyloxy-chalcone 31g were the most active compounds against T. rubrum and T. mentagrophytes and A. fumigatus , respectively (MICs = 62.5 μg/mL). Hemolytic activity studies and in silico toxicity analysis demonstrated that most of the compounds are safe.
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