SYNTHESIS, CHARACTERIZATION AND ANTIBACTERIAL ACTIVITY OF [1,2,4]TRIAZOLO[4,3-B][1,2,4,5]TETRAZINE DERIVATIVES

Bassam A. Hassan, Athraa H. Mekky

Abstract

A series of fused heterocyclic compound triazolotetrazine were prepared from the reaction of equimolar amount of 4-amino-5-phenyl-4H-1,2,4-triazole-3-thiol via cyclization addition reaction with different aromatic aldehydes in presence of piperidine as catalyst to produce the target [1,2,4]triazolo[4,3- b][1,2,4,5] tetrazine derivatives. The synthesized compounds were characterized by spectral methods (FT-IR and 1H-NMR, 13C-NMR and mass). The newly synthesized compounds exhibited an anticancer effect when these compounds were docked inside the C-Met tyrosine kinase receptor. As shown by their docking scores, they range from -5.599 to -4.403 Kcal/mol, whereas Crizotinib binding affinity is -3.211 Kcal/mol. For antibacterial efficiency, 4e and 4f testing on a series of bacteria, Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, and Klebsiella, respectively, reveals that the compounds have exhibited moderate activity against negative and positive bacteria. Antifungal activity of (4g, 4i) was assessed against the representative typical fungi such as Candidiasis fungal and compared with Fluconazole as an antifungal drugs. The results indicated that tested compounds had good fungicide activity, which has good growth inhibition against Candidiasis.

https://doi.org/10.32737/2221-8688-2025-1-78-94