Synthesis and antimicrobial activity of esters of 3-ethoxy-4-hydroxybenzaldehyde oxime

Ahluwalia, Vivek; Kumar, Jitendra; Rana, Virendra Singh; Singh, Vikram; Sati, O. P.; Walia, Suresh; Garg, Nandini

doi:10.1080/02772248.2016.1166227

Cited by 9 publications

(6 citation statements)

References 23 publications

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“…The ester's ability to inhibit P. gingivalis was further confirmed with the current study. In addition, other studies confirmed the antimicrobial property of esters against Gram-positive and Gram-negative bacteria [32][33][34]. This study revealed that compound (2) exhibits MBC against P. gingivalis but not against other tested microorganisms, suggesting that compound (2) has bacteriostatic activity against other tested pathogens in the present study (Table 2).…”

Section: Biological Activity 221 In Vitro Antibacterial Activity Of S...supporting

confidence: 80%

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: Biological Activity 221 In Vitro Antibacterial Activity Of S...supporting

confidence: 80%

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

et al. 2022

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“…It was reported that oxime esters exhibited insecticidal [ 16 , 17 ], herbicidal [ 18 ], antiviral [ 19 ], antitumor [ 20 , 21 , 22 ], and antibacterial activities [ 23 , 24 , 25 ]. For example, a series of 3-ethoxy-4-hydroxybenzaldehyde oxime esters were synthesized and evaluated for their in vitro antifungal activity against three pathogenic fungi and antibacterial activity against three bacterial strains, and the structure-activity relationship was also preliminarily summarized [ 26 ]. In continuation of our interest in the bioactive properties of natural product-based compounds [ 27 , 28 , 29 , 30 , 31 , 32 , 33 ], a series of novel 3-caren-5-one oxime esters were designed and synthesized by integrating bioactive oxime esters into the skeleton of 3-carene.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antifungal Activity of Novel 3-Caren-5-One Oxime Esters

et al. 2017

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A series of novel 3-caren-5-one oxime esters were designed and synthesized by multi-step reactions in an attempt to develop potent antifungal agents. Two E-Z stereoisomers of the intermediate 3-caren-5-one oxime were separated by column chromatography for the first time. The structures of all the intermediates and target compounds were confirmed by UV-Vis, FTIR, NMR, ESI-MS, and elemental analysis. The antifungal activity of the target compounds was preliminarily evaluated by the in vitro method against Fusarium oxysporum f. sp. cucumerinum, Physalospora piricola, Alternaria solani, Cercospora arachidicola, Gibberella zeae, Rhizoeotnia solani, Bipolaris maydis, and Colleterichum orbicalare at 50 µg/mL. The target compounds exhibited best antifungal activity against P. piricola, in which compounds (Z)-4r (R = β-pyridyl), (Z)-4q (R = α-thienyl), (E)-4f′ (R = p-F Ph), (Z)-4i (R = m-Me Ph), (Z)-4j (R = p-Me Ph), and (Z)-4p (R = α-furyl) had inhibition rates of 97.1%, 87.4%, 87.4%, 85.0%, 81.9%, and 77.7%, respectively, showing better antifungal activity than that of the commercial fungicide chlorothanil. Also, compound (Z)-4r (R = β-pyridyl) displayed remarkable antifungal activity against all the tested fungi, with inhibition rates of 76.7%, 82.7%, 97.1%, 66.3%, 74.7%, 93.9%, 76.7% and 93.3%, respectively, showing better or comparable antifungal activity than that of the commercial fungicide chlorothanil. Besides, the E-Z isomers of the target oxime esters were found to show obvious differences in antifungal activity. These results provide an encouraging framework that could lead to the development of potent novel antifungal agents.

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“…Among the benzaldehyde derivatives, ethyl vanillin and its oxime were previously investigated for their antimicrobial potential. In the study conducted by Morris et al ethyl vanillin proved moderate activity toward E.coli (MIC = 1000 ppm) and C. albicans (MIC = 1000 ppm) 47 , while in other studies its oxime did not prove growth inhibitory activity against S. aureus (MIC > 50,000 mg/L) and P. aeruginosa (MIC > 50,000 g/L) 48 . In our study ethylvanillin presented very good activity towards C. albicans (MIC = 150.00 mg/L) and moderate activity toward A. brasiliensis (MIC = 300.00 mg/L) and L. pneumophila (MIC = 300.00 mg/L) while its oxime weakly inhibited growth of E. hirae (MIC = 600.00 mg/L) , C. albicans (MIC = 900.00 mg/L) and moderately of A. brasiliensis (MIC = 300.00 mg/L) .…”

Section: Discussionmentioning

confidence: 92%

Cytotoxicity, early safety screening, and antimicrobial potential of minor oxime constituents of essential oils and aromatic extracts

Surowiak

Sowała

Talma

et al. 2022

Sci Rep

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Due to market and legislative expectations, there is a constant need to explore new potential antimicrobial agents for functional perfumery. In this study, we evaluated the antimicrobial activity of 53 low molecular oximes and the corresponding carbonyl compounds against Escherichia coli, Enterococcus hirae, Pseudomonas aeruginosa, Bacillus cereus, Staphylococcus aureus, Aspergillus brasiliensis, Legionella pneumophila and Candida albicans. The most potent compound was α-isomethylionone oxime, which exhibited a minimum inhibitory concentration (MIC) of 18.75 µg/mL against E. hirae. The evaluation of the MICs for bacterial and fungal strains was performed for selected compounds, for example, the MIC of 2-phenylpropionaldehyde, cis-jasmone oxime, and trans-cinnamaldehyde measured against A. brasiliensis was 37.50 µg/mL. ADME-Tox (Absorption, Distribution, Metabolism, Excretion, and Toxicity) and 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium (MTS) cell viability assays were performed to assess the cytotoxicity of tested compounds. ADME-Tox indicated the safety and promising properties of selected compounds, which enables their usage as nontoxic supporting antibacterial agents. The results of the in vitro MTS assay were consistent with the ADME-Tox results. None of the compounds tested was toxic to Human Embryonic Kidney 293T (HEK293T) cells, with all cell viabilities exceeding 85%.

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Synthesis and antimicrobial activity of esters of 3-ethoxy-4-hydroxybenzaldehyde oxime

Cited by 9 publications

References 23 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

Synthesis and Antifungal Activity of Novel 3-Caren-5-One Oxime Esters

Cytotoxicity, early safety screening, and antimicrobial potential of minor oxime constituents of essential oils and aromatic extracts

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