Design, synthesis and evaluation of novel substituted fused pyrido diazepine and pyrimido piperazine derivatives: In vitro cytotoxicity study over various cancer cell lines

Timaniya, Jignesh B.; Parikh, Paranjay; Patel, Mrugesh; Dave, Gayatri; Patel, Kaushal P.

doi:10.1016/j.rechem.2022.100707

Cited by 1 publication

(1 citation statement)

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“…These fragments are present in a large number of drugs and bioactive molecules, which can establish different types of chemical interactions (hydrogen bonds, π-stacking interactions, among others) with biological systems [5][6][7][8][9]. Thus, 1,3,5-triazine-, pyrimidine-, and diazepine heterocyclic moieties are present in diverse molecules exhibiting multiple biological properties acting as antioxidants [10,11], anti-HIV [12][13][14], anticonvulsants [15,16], antimicrobials [17][18][19], anticancer [20][21][22][23], among others [24,25].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Triazine-Based Chalcones and 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as Potential Leads in the Search of Anticancer, Antibacterial and Antifungal Agents

Moreno,

Quiroga,

Abonia

et al. 2024

IJMS

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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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