Synthesis and Characterization of Triazine Derivatives and Their Bacteriostatic Evaluation

Nur Alia Syahilda, Zikri (2024) Synthesis and Characterization of Triazine Derivatives and Their Bacteriostatic Evaluation. Masters thesis, Universiti Malaysia Sarawak.

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Abstract

Triazine is a heterocyclic compound with a nitrogen-rich ring structure, has gained attention for its unique reactivity and versatility, making it a valuable building block in organic synthesis and pharmacological applications through chemical modifications. In this study, three series of triazine derivatives 35a-e, 39a-g, and 42a-g bearing different pharmacophores have been successfully synthesized and characterized using FT-IR, 1H and 13C NMR spectroscopies. Triazinethione derivatives 35a-e were synthesized via Diels-Alder’s cyclization reaction between guanidine hydrochloride with various isothiocyanate intermediates derivatives, while precursor triazine-amine 39a-g were prepared by using cyanuric chloride via nucleophilic substitution with substituted aniline derivatives. The subsequent reaction of 39a-g with thiourea yielded triazine-bis(thiourea) 42a-g. The antibacterial activities of the series were evaluated against bacteria Escherichia coli (ATCC 25922) and Staphylococcus aureus (S48/81) via the Kirby Bauer disc diffusion method. Among all compound, compound 39d and 42d bearing fluoro exhibits strong antibacterial activities (p<0.01) against S. aureus with 10 mm and 10.5 mm which is comparable to the standard drug ampicillin 11.0 mm. The remaining compound 39a-g and 42a-g shows weak to moderate inhibition against both bacterial strains. Moreover, compound 42b-g showed better antibacterial properties against S. aureus but declined against E. coli. The enhanced antibacterial activities of the compound are attributed to the synergistic combination of a triazine ring, an amino aromatic group, and the thiourea functional group.

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