Synthesis, Characterization and Biological Evaluation of Novel Benzamidine Derivatives: Newer Antibiotics for Periodontitis Treatment

Abstract

Periodontal disease (PD) is complex polymicrobial disease which destroys tooth-supporting tissue. Although various synthetic inhibitors of periodontitis-triggering pathogens have been recognized, their undesirable side effects limit their application. Hence, the present study intended to perform the synthesis, characterization, antimicrobial evaluation, and cytotoxicity analysis of novel benzamidine analogues (NBA). This study involved the synthesis of novel imino bases of benzamidine (4a–c), by reacting different aromatic aldehydes with 2-(4-carbamimidoylphenoxy) acetohydrazide (3), which was synthesized by the hydrazination of ethyl 2-(4-carbamimidoylphenoxy) acetate (2), the derivative of 4-hydroxybenzene carboximidamide (1). This was followed by characterization using FTIR, 1H, 13C NMR and mass spectrometry. All synthesized compounds were further tested for antimicrobial potential against PD-triggering pathogens by the micro broth dilution method. The cytotoxicity analysis of the NBA against HEK 293 cells was conducted using an MTT assay. The present study resulted in a successful synthesis of NBA and elucidated their structures. The synthesized NBA exhibited significant antimicrobial activity values between 31.25 and 125 µg/mL against tested pathogens. All NBA exhibited weak cytotoxicity against HEK 293 cells at 7.81 µg, equally to chlorhexidine at 0.2%. The significant antimicrobial activity of NBA against PD-triggering pathogens supports their potential application in periodontitis treatment.

Synthesis, Characterization and Response of Newer Benzamidine Analogues against Porphyromonas gingivalis mediated Peri-Implantitis

“…The antimicrobial and cell viability research on novel benzamidine analogues (NBA) indicated that presence of NO 2 and Cl (electron withdrawing groups) in compounds 3a and 3b, respectively on 4 th position of benzyl ring offers significant MIC, MBC and safety. Findings of current investigation were also found to agree with the findings of other investigations on inhibitory response of benzamidines towards P. gingivalis [1][2][3]23,24]. Therefore, the current cell viability and antimicrobial research findings supports significant safety and efficacy of NBA.…”

“…Hence based on high docking score of molecules L, 1, 1a, 2a-c and 3a-c, it was decided to carry out the synthesis, optimization and characterization of compounds 3a-c and determine their inhibitory potential (MIC and MBC) against P. gingivalis, followed by cytotoxicity against healthy human cells (HEK 293). Present study successfully synthesized and elucidated the physical and chemical properties of azetidinones, which were also correlated with the other studies [18,23,24]. Similar procedures and results were also highlighted by other studies [30,31].…”

“…Novel benzamidine analogues (NBA, 3a-c) were synthesized as per the method stated in standard literature with minor modification [23,24]. Briefly, compound (0.0002 M) (previously synthesized by Schiff reaction of compound 1 with 4-nitrobenzaldehyde) was dissolved in 1,4-dioxane and chloroacetyl chloride (0.00025 M), followed by dropwise addition of triethyl amine (0.0003 M) with constant stirring at low temperature (0-5 ºC).…”

Synthesis, Characterization, Docking Studies and in vitro Response of New Camptothecin Derivatives towards Oral Squamous Cell Carcinoma

“…Synthesis of 10,19-diethyl- [19,20]. Briefly, hydrazinated derivative of irinotecan 1 {(that was obtained after esterification and hydrazination of irinotecan (CPT-11)} was refluxed with chlorobenzaldehyde in equimolar concentration for 8 h. For the reaction, just quantity sufficient (Q.S.)…”

Imidazo[1,2‐a]pyridine as a promising scaffold for the development of antibacterial agents

“…Recently various antibacterial agents integrated with heterocyclic frameworks such as quinazoline [12, 13], coumarin [14, 15], pyrazole [16, 17], imidazole [18, 19], flavones [20, 21], benzimidine [22, 23] etc. were identified as effective antibacterial drugs.…”