Vanillin containing 9H-fluoren sulfone scaffolds: Synthesis, biological evaluation and molecular docking study

Narode, Hanuman; Gayke, Manoj; Bhosale, Rajesh S.; Gyanchander, Eppa; Gohil, Nisarg; Bhattacharjee, Gargi; Singh, Vijai; Pawar, Rajendra P.; Rajani, Dhanaji P.; Yadav, J. S.

doi:10.1016/j.rechem.2021.100269

Cited by 9 publications

(8 citation statements)

References 34 publications

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“…In sterile 96‐well plates using the broth dilution method, the antifungal assay for all synthesized amide‐coupled naphthalene scaffolds was conducted [25] against the fungi C. albicans (MTCC 227), A. niger (MTCC 282) and A. clavatus (MTCC 1323) obtained from the MTCC, Chandigarh, India. The medication griseofulvin was taken into consideration as a positive control.…”

Section: Methodsmentioning

confidence: 99%

“…MIC was measured using a microbroth dilution method to assess the antibacterial activity of the synthesized naphthalene derivatives [25–28] . According to CLSI (Clinical and Laboratory Standards Institute) guidelines, the test was conducted on the bacterial strains E. coli (MTCC 443), P. aeruginosa (MTCC 1688), S. aureus (MTCC 96), and S. pyogenes (MTCC 442) obtained from the Microbial Type Culture Collection (MTCC), Chandigarh, India.…”

Section: Methodsmentioning

confidence: 99%

“…A molecular docking study was carried out to comprehend the molecular interaction of amino acid coupled naphthalene scaffolds with DNA gyrase (1AJ6) and topoisomerase IV (1S14) proteins. Using Chem3D 16.0, all amino acid coupled naphthalene scaffolds ( 6 a – i ) were drawn and accessed as mol2 files [25] . In addition to being used for analysis and visualization, the UCSF Chimaera 1.12 package has been used for molecular docking [33] .…”

Section: Methodsmentioning

confidence: 99%

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New Amino Acids Naphthalene Scaffolds as Potent Antimicrobial Agents: In Vitro Assay and In Silico Molecular Docking Study

Kalariya,

Pandya,

Gohil

et al. 2024

ChemistrySelect

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The development of innovative antifungal medications to address the issues of indiscriminate antifungal use contributes to certain antifungal drug resistance. To tackle this issue, we have designed and synthesized novel amino acids naphthalene scaffolds (6 a–6 i) (Scheme 1) by acid amine coupling between compound 5 and various amino acids. Moreover, we evaluated the antifungal, anti‐bacterial and antimalarial activities of synthesized derivatives. Among them, compounds Met (6 a), Phe (6 c), Lys (6 d), Ser (6 f), and Tyr (6 i) expressed excellent antifungal activity at a minimum inhibitory concentration (MIC) value of 250 μg/mL against Candida albicans compared to standard drug griseofulvin (500 μg/mL). The antibacterial assay results showed that compound Met (6 a) exhibited effective antibacterial activity at MIC value at 50 and 62.5 μg/mL against Streptococcus pyogenes and Pseudomonas aeruginosa respectively, and compound Trp (6 g) showed very good antibacterial activity at MIC 62.5 μg/mL against Staphylococcus aureus. The antimalarial activity of synthesized compoundsVal (6 b) and Lys (6 d) showed moderately active with mean IC50 of 0.69 and 0.47 μg/mL, respectively compared with standard drug quinine (IC50=0.26 μg/mL). Also, a molecular docking study was performed to demonstrate the binding energy of synthesized scaffoldswith effective interaction with various proteins. The compound Met (6 a) showed that the highest binding affinity (binding energy: −7.1 kcal/mol) which interacted more effectively with VAL 120 (2.90 Å).

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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New Amino Acids Naphthalene Scaffolds as Potent Antimicrobial Agents: In Vitro Assay and In Silico Molecular Docking Study

Kalariya,

Pandya,

Gohil

et al. 2024

ChemistrySelect

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“…Three fungal strains, namely, C. albicans (MTCC 227), A. niger (MTCC 282) and A. clavatus (MTCC 1323) were used for determining the antifungal efficacy of synthesized indoline derivatives using broth dilution method [26,27]. The standard antifungal drug griseofulvin was used as positive control.…”

Section: Antifungal Activitymentioning

confidence: 99%

Novel 9H‐flouren containing indoline scaffolds: Synthesis, characterization, antimicrobial assays, and molecular docking study

Gangapuram,

Tanguturi,

Gohil

et al. 2024

Journal of Heterocyclic Chem

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Abstract9H fluoren containing indoline scaffolds were developed by coupling indoline amine with α‐carboxylic acid group of amino acids in the presence of the peptide coupling reagent hexafluorophosphate benzotriazole tetramethyluronium (HBTU). All eight (12a–12h) synthesized indoline scaffolds were analyzed for their potent antibacterial and antifungal activities. The antibacterial assay revealed that compounds 12a, 12b, and 12e have shown excellent activity against pathogenic strains Pseudomonas aeruginosa, Staphylococcus aureus, and Streptococcus pyogenes with minimum inhibitory concentration (MIC) values as low as between 25 and 125 μg/mL. The antifungal activity of all synthesized indoline scaffolds were moderate compared with used standard drugs. The molecular docking study of 12a, 12b, and 12e with various antibacterial target proteins from different bacterial strains revealed outstanding interactions which ultimately support antibacterial results.

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“…From the outcomes, it indicated that the compound containing azomethine group with sulfomoyl moiety and phenyl carboxylate system showed potent anticancer activity 3 . 40) was synthesized by reacting vanillin with 1,10-phenanthroline-5,6-dione and evaluated against human colorectal carcinogenic cell lines such as HT29 and HCT116 cells. The tested compound was found to be highly active against colorectal cancer, determined by the inhibition of Wnt/β-catenin signaling pathway.…”

Section: Antiviral Activitymentioning

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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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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Vanillin containing 9H-fluoren sulfone scaffolds: Synthesis, biological evaluation and molecular docking study

Cited by 9 publications

References 34 publications

New Amino Acids Naphthalene Scaffolds as Potent Antimicrobial Agents: In Vitro Assay and In Silico Molecular Docking Study

New Amino Acids Naphthalene Scaffolds as Potent Antimicrobial Agents: In Vitro Assay and In Silico Molecular Docking Study

Novel 9H‐flouren containing indoline scaffolds: Synthesis, characterization, antimicrobial assays, and molecular docking study

Therapeutic aspects of biologically potent vanillin derivatives: A critical review

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