| Summary: | Periodontal disease (PD) is multifactorial oral disease that damages tooth-supporting tissue. PD treatment includes proper oral hygiene, deep cleaning, antibiotics therapy, and surgery. Despite the availability of basic treatments, some of these are rendered undesirable in PD treatment due to side effects and expense. Therefore, the aim of the present study is to develop novel molecules to combat the PD triggering pathogens. The study involved the synthesis of 4-((5-(substituted-phenyl)-1,3,4-oxadiazol-2-yl)methoxy)benzamidine (<b>5a-e</b>), by condensation of 2-(4-carbamimidoylphenoxy)acetohydrazide (<b>3</b>) with different aromatic acids; and synthesis of 4-((4-(substituted benzylideneamino)-4H-1,2,4-triazol-3-yl)methoxy)benzamidine <i>(</i><b>6a-b</b>) by treatment of <b>compound 3</b> with CS<sub>2</sub> followed by hydrazination and a Schiff reaction with different aromatic aldehydes. Synthesized <b>compounds</b> were characterized based on the NMR, FTIR, and mass spectrometric data. To assess the effectiveness of the newly synthesized <b>compound</b> in PD, new <b>compounds</b> were subjected to antimicrobial evaluation against <i>P. gingivalis</i> and <i>E. coli</i> using the micro-broth dilution method. Synthesized <b>compounds</b> were also subjected to cytotoxicity evaluation against HEK-293 cells using an MTT assay. The present study revealed the successful synthesis of heterocyclic derivatives of benzamidine with significant inhibitory potential against <i>P. gingivalis</i> and <i>E. coli</i>. Synthesized <b>compounds</b> exhibited minimal to the absence of cytotoxicity. Significant antimicrobial potential and least/no cytotoxicity of new heterocyclic analogs of benzamidine against PD-triggering bacteria supports their potential application in PD treatment.
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