Synthesis of novel Schiff bases containing arylpyrimidines as promising antibacterial agents

Nayak, Soukhyarani Gopal; Poojary, Boja

doi:10.1016/j.heliyon.2019.e02318

Cited by 30 publications

(12 citation statements)

References 25 publications

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“…In recent years, imine bases demonstrated excellent antibacterial activities with some studies reporting that it possesses better inhibition activity than some commonly used antibiotics [ 39 ]. Although imine bases are continuously being evaluated for their antimicrobial properties against bacteria, there are fewer studies when it comes to P. gingivalis growth inhibition.…”

Section: Resultsmentioning

confidence: 99%

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

et al. 2022

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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.

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Section: Resultsmentioning

confidence: 99%

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

et al. 2022

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“…Evaluation of the compounds MIC was determined by spotting 5 µL of each concentration of L1 – L5 and Q1 – Q15 on the MHA plates, and the plates were incubated at 37 °C for 18 h. These procedures were done in triplicate to give the accurate lowest concentration of the compounds where no visible bacterial growth was seen after incubation. Ciprofloxacin was used as a standard and DMSO used as a negative control showed no bactericidal effect against all the bacteria strains [ 50 , 62 , 103 ].…”

Section: Methodsmentioning

confidence: 99%

Quinoline Functionalized Schiff Base Silver (I) Complexes: Interactions with Biomolecules and In Vitro Cytotoxicity, Antioxidant and Antimicrobial Activities

et al. 2021

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A series of fifteen silver (I) quinoline complexes Q1–Q15 have been synthesized and studied for their biological activities. Q1–Q15 were synthesized from the reactions of quinolinyl Schiff base derivatives L1–L5 (obtained by condensing 2-quinolinecarboxaldehyde with various aniline derivatives) with AgNO3, AgClO4 and AgCF3SO3. Q1–Q15 were characterized by various spectroscopic techniques and the structures of [Ag(L1)2]NO3Q1, [Ag(L1)2]ClO4Q6, [Ag(L2)2]ClO4Q7, [Ag(L2)2]CF3SO3Q12 and [Ag(L4)2]CF3SO3Q14 were unequivocally determined by single crystal X-ray diffraction analysis. In vitro antimicrobial tests against Gram-positive and Gram-negative bacteria revealed the influence of structure and anion on the complexes′ moderate to excellent antibacterial activity. In vitro antioxidant activities of the complexes showed their good radical scavenging activity in ferric reducing antioxidant power (FRAP). Complexes with the fluorine substituent or the thiophene or benzothiazole moieties are more potent with IC50 between 0.95 and 2.22 mg/mL than the standard used, ascorbic acid (2.68 mg/mL). The compounds showed a strong binding affinity with calf thymus-DNA via an intercalation mode and protein through a static quenching mechanism. Cytotoxicity activity was examined against three carcinoma cell lines (HELA, MDA-MB231, and SHSY5Y). [Ag(L2)2]ClO4Q7 with a benzothiazole moiety and [Ag(L4)2]ClO4Q9 with a methyl substituent had excellent cytotoxicity against HELA cells.

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“…Many studies on the synthesis of azomethine compounds have been reported [42,43], but they all suffer from one or more serious shortcomings, such as high environmental pollution due to the solvent and reaction hardness, high temperature, multistep pathways, and long reaction times with low-to-moderate yields under severe reaction conditions. Recently, one of the most intriguing areas in the synthesis of widely used organic compounds is the focus on benign environmentally friendly conditions and reagents such as catalysts.…”

Section: Comparative Synthesis Of Compounds 3(a-c) Comparative Studymentioning

confidence: 99%

Highly efficient and recyclable novel spindles Fe2O3@SiO2/In2O3 nanomagnetic catalyst designed for green synthesis of azomethine compounds

et al. 2022

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A novel and reusable nanomagnetic catalyst, Fe2O3@SiO2/In2O3, was synthesized by a facile chemical approach in three successive steps. The nanocatalyst was characterized by FT-IR, XRD, SEM, EDX, TEM, and VSM. The XRD pattern displays the characteristic peaks of Fe2O3 and SiO2, accompanied by new peaks assigned to different planes of In2O3 that confirm the formation of In2O3 on the surface of Fe2O3@SiO2 core/shell spindles. The TEM micrographs show spindle-like particles of Fe2O3 covered with SiO2 shell, and the In2O3 nanoparticles in an average diameter of 20 nm are hung on the surface of the Fe2O3@SiO2. The nanomagnetic catalyst Fe2O3@SiO2/In2O3 was used for the transformation of the (4-nitrophenyl)-1-phenyl-1H-pyrazole-5-amine, and chalcones derivatives, into valuable azomethine compounds of 3-(substituted)-1-(pyridine-2-yl)allylidene)-3-(4-nitrophenyl)-1-phenyl-1H-pyrazole-5-amine with high rate and efficient catalyst recovery. The yield obtained through the catalytic route reached 90–95% in shorter reaction times compared with uncatalyzed reaction method. Graphical abstract

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Synthesis of novel Schiff bases containing arylpyrimidines as promising antibacterial agents

Cited by 30 publications

References 25 publications

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

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

Quinoline Functionalized Schiff Base Silver (I) Complexes: Interactions with Biomolecules and In Vitro Cytotoxicity, Antioxidant and Antimicrobial Activities

Highly efficient and recyclable novel spindles Fe2O3@SiO2/In2O3 nanomagnetic catalyst designed for green synthesis of azomethine compounds

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