Antimicrobial effects of vanillin‐based pyridyl‐benzylidene‐5‐fluoroindolins

Mohanraj, Deena Gladies Raymond; Subramaniam, Palaniraja; Bakthavachalam, Dhivya; Sivakumar, A.; Chellam, Subha

doi:10.1002/jhet.4277

Cited by 6 publications

(2 citation statements)

References 21 publications

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“…The in vitro antimicrobial effect was analyzed through the agar well diffusion method against fungal (Candida albicans), gram-positive bacterial (Streptococcus pyogenes, Staphylococcus aureus) and gramnegative bacterial (P. aeruginosa, E. coli) species. Thus, the vanillin pyridyl-based derivatives showed broad-spectrum antimicrobial activity against bacterial and fungal species with better DNA gyrase inhibition 9 . Vanillin chalcone derivatives,…”

Section: Activity Of Vanillin Derivativesmentioning

confidence: 99%

“…In contrast to more effective phenolic antimicrobials, the vanillin derivatives were found to be highly bacteriostatic 6,7 . Vanillin is a non-toxic and bioactive substance with a wide range of pharmacological activity including anticancer and antioxidant 6,8 , antimicrobial 9 , antimycobacterial 10 , antiviral 11 , antimalarial 12 , antiinflammatory 13 , anti-Alzheimer 14 , anti-sickling 15 and antidiabetic 16 activities.…”

Section: Introductionmentioning

confidence: 99%

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Therapeutic aspects of biologically potent vanillin derivatives: A critical review

Senthil Kumar,

Naveena,

Praveen

et al. 2023

J. Drug Delivery Ther.

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4-hydroxy 3-methoxy benzaldehyde (Vanillin) is an aromatic phenolic aldehyde with unique chemical properties and pharmacological impact. Because of its potent nature, it acts as a lead for drug discovery and development techniques. Heterocyclic compounds with vanillin moiety were efficacious and thrive against many emerging infectious diseases, which can also lead to develop numerous fused heterocyclic vanillin derivatives and various heterocyclic compounds such as pyrimidines, quinoxalines, imidazoles or thiazoles. Greener-mediated synthesis is a sustained chemical reaction used to synthesize hazardless vanillin derivatives with a high yield of product in desired time. Due to its several reasonable modifications with high bioactivity, vanillin moiety can be used to develop various potent derivatives like vanillin-based ferrocenyl chalcone derivatives, vanillin-hydrazone derivatives, Schiff base and Mannich base-based derivatives, pyrazoline vanillin-based derivatives, triazole-based vanillin derivatives and vanillin hybrids plays a crucial role in the coordination chemistry. These derivatives exhibited plenty of biological applications, which include anticancer, antioxidant, antibacterial, antitubercular, antimalarial, antiviral, anti-inflammatory, anti-Alzheimer and anti-diabetic effects. Hence, this review focuses on the significance of vanillin derivatives responsible for biological activity. Keywords: Vanillin; 4-hydroxy 3-methoxy benzaldehyde; Vanillin derivatives; Antimicrobial; Anticancer; Biological applications

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Section: Activity Of Vanillin Derivativesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Therapeutic aspects of biologically potent vanillin derivatives: A critical review

Senthil Kumar,

Naveena,

Praveen

et al. 2023

J. Drug Delivery Ther.

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Novel pyrazole‐biphenyl‐carboxamides for SARS‐CoV2 entry‐level restriction and microbial infections

Samy,

Dangate,

Alagumuthu

2024

Journal of Heterocyclic Chem

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Microbial diseases including viral infection are big issues globally. Effective medicinal discovery for them is the need for the day. In this study, we report pyrazole‐biphenyl‐carboxamides (4a‐l) validated for their SARS‐CoV2 entry‐level restriction effect over studying the protein–protein interaction of SARS‐CoV2 with human ACE protein. Their extended antimicrobial properties were also evaluated. Online and offline software tools predicted MD simulation and ADMET druggability in silico. The antimicrobial efficacy of all compounds was also evaluated against Gram+ve Streptococcus pneumoniae (MTCC 1936), Staphylococcus aureus (MTCC 737) and Gram‐ve Escherichia coli (MTCC 443), Pseudomonas aeruginosa (MTCC 424) (bacteria). In the results, compounds 4g and 4i were evenly active against both bacteria at a low concentration range (MIC: 1.00 to 9.5 μg/mL) and displayed lesser toxicity to tested mammalian cells (EC100 = 75 μg/mL). Furthermore, it was able to kill metabolically inactive bacterial cells and eradicate established biofilms of Methicillin‐resistant Staphylococcus aureus (MRSA). Both the compounds inhibited DNA gyrase well with an IC50 0.25 μM (96% relative activity) and 0.52 μM (97% relative activity) respectively. Compounds (4a‐l) showed restrictive efficiency of SARS‐CoV2 spike protein (SC2SP) and human angiotensin‐converting enzyme 2 (hACE2) entry‐level association in COVID‐19 in silico. To assess this ability, firstly, we identified the crucial amino acid residues involved in the interface of SARS‐CoV‐2 and hACE2 virtually. We recognized the ability of 4a‐l binding to the binding interface to SARS‐CoV2; thus, the interaction of SC2SP‐hACE2 was effectively inhibited.

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Synthesis and molecular docking simulation on the antimicrobial effects of halogenated vanillin-azo dyes and schiff base derivatives

Hissam,

Ngaini,

Zamakshshari

et al. 2024

Discov Appl Sci

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Lead compounds containing nitrogen pharmacophores from natural resources have garnered interest among researchers due to their potential for drug development. However, the extractions of the active metabolites are usually labor-intensive and time-consuming. In this study, halogenated vanillin derivatives featuring azo dyes (N=N) (1a-1 h) and Schiff base (C=N) (2a-2 h) have been synthesized via diazonium coupling and nucleophilic substitution reaction, respectively. The comparative effect of N=N and C=N moieties was evaluated for antibacterial properties against Staphylococcus aureus and Escherichia coli via disc diffusion method. Incorporating C=N (8–13 mm) into the vanillin network showed excellent inhibition against S. aureus compared to N=N (7–8 mm) and the standard ampicillin (12 mm). While the halogenated vanillin featuring N=N (7–9 mm) and C=N (7–8 mm) moieties showed excellent zone of inhibitions against E. coli compared to the parent vanillin. The in-silico screening using AutoDock Vina, showed 2c-h (inhibition zone > 10 mm) with a high binding affinity against DNA gyrase enzyme with binding energy ranging from − 7.3 to − 7.9 kcal/mol, similar to re-docking of ampicillin − 7.6 kcal/mol and co-crystalize compounds BPH651 with − 7.5 kcal/mol. This research contributes a significant milestone in drug design, especially for the development of new antibacterial drugs with outstanding properties. Graphical abstract

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Antimicrobial effects of vanillin‐based pyridyl‐benzylidene‐5‐fluoroindolins

Cited by 6 publications

References 21 publications

Therapeutic aspects of biologically potent vanillin derivatives: A critical review

Therapeutic aspects of biologically potent vanillin derivatives: A critical review

Novel pyrazole‐biphenyl‐carboxamides for SARS‐CoV2 entry‐level restriction and microbial infections

Synthesis and molecular docking simulation on the antimicrobial effects of halogenated vanillin-azo dyes and schiff base derivatives

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