Experimental and computational approaches of a novel methyl (2E)-2-{[N-(2-formylphenyl)(4-methylbenzene)sulfonamido]methyl}-3-(4-chlorophenyl)prop-2-enoate: A potential antimicrobial agent and an inhibition of penicillin-binding protein

Murugavel, S.; velan, V. Vetri; Kannan, D.; Bakthadoss, Manickam

doi:10.1016/j.molstruc.2016.02.084

Cited by 20 publications

(7 citation statements)

References 87 publications

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“…Table 6 findings demonstrate that derivatives 4 b , 5 b , 4 c , 5 c , 4 d , 5 d , 4 e , 4 f , and 5 g met all of Lipinski's rules. According to Veber's rule, compounds with ten or fewer rotatable bonds and a TPSA of equal to or less than 140 Å 2 are also considered drug‐like, and this supports the derived compounds [68,69] …”

Section: In Vitro Biological Evaluationmentioning

confidence: 65%

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Exploration of N‐(6‐Indazolyl) benzenesulfonamide Derivatives as Potential Antioxidants and Antimicrobial Agents: Integrating Synthesis, In Silico Docking, and Bioactivity Profiling

Yadav,

Rao,

Kumar

et al. 2023

ChemistrySelect

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A new series of N‐(1‐(2‐chloropyrimidin‐4‐yl)‐1H‐indazol‐5‐yl) benzenesulfonamide derivatives (4 a–i) and N‐(1‐(2‐chloropyrimidin‐4‐yl)‐6‐ethoxy‐1H‐indazol‐5‐yl) benzenesulfonamide derivatives (5 a–i) was synthesized via reduction of 1‐(2‐halopyrimidin‐4‐yl)‐5‐nitro‐1H‐indazole (3) with SnCl2 followed by reaction with various aryl sulphonyl chlorides in pyridine. The structures were confirmed using IR, 1H‐NMR, 13C‐NMR, and mass spectral methods. Compounds 4 a–i and 5 a–i were evaluated for antifungal and antibacterial activities against Gram‐negative and Gram‐positive bacteria. They also exhibited antioxidant potential in DPPH (IC50=0.094‐0.467 μmol/ml) and ABTS assays (IC50=0.101–0.496 μmol/ml). Remarkably, N‐(1‐(2‐chloropyrimidin‐4‐yl)‐1H‐indazol‐5‐yl)‐2‐nitrobenzenesulfonamide displayed the highest antibacterial activity, while N‐(1‐(2‐chloropyrimidin‐4‐yl)‐1H‐indazol‐5‐yl)‐4‐methoxybenzenesulfonamide showed excellent antifungal potential. Compound N‐(1‐(2‐chloropyrimidin‐4‐yl)‐1H‐indazol‐5‐yl)‐2‐nitrobenzenesulfonamide exhibited the most significant antioxidant activity. In this study, molecular dynamics simulations were utilized to rigorously examine the stability of ligand‐protein complexes, demonstrating a consistent and robust binding of the most potent compound within the target proteins′ binding sites. Computational assessments were further employed to predict the drug‐likeness and ADMET properties of the synthesized compounds. The results unequivocally confirmed the remarkable antioxidant and antimicrobial potential of all derivatives, a finding substantiated by comprehensive molecular docking analyses that revealed intricate interactions involving hydrogen bonds, electrostatic forces, and hydrophobic contacts. These findings collectively provide invaluable insights into the complex molecular structure and receptor target site dynamics, laying a strong foundation for the development of novel active antioxidant and antimicrobial agents with promising pharmaceutical implications.

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Section: In Vitro Biological Evaluationmentioning

confidence: 65%

“…According to Veber's rule, compounds with ten or fewer rotatable bonds and a TPSA of equal to or less than 140 Å 2 are also considered drug-like, and this supports the derived compounds. [68,69]…”

Section: Drug Likeness Parametersmentioning

confidence: 99%

Exploration of N‐(6‐Indazolyl) benzenesulfonamide Derivatives as Potential Antioxidants and Antimicrobial Agents: Integrating Synthesis, In Silico Docking, and Bioactivity Profiling

Yadav,

Rao,

Kumar

et al. 2023

ChemistrySelect

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“…The detail has been discussed in cartoon representation with highlighted portions in Figure 5 . In a study, Murugavel et al [ 41 ] revealed the inhibitory activity of methyl (2E)-2-{[N-(2-formylphenyl) (4-methylbenzene)sulfonamido]methyl}-3-(4-chlorophenyl) prop-2-enoate (MFMSC) when docked against PBP-2X. Similarly, Levy et al [ 42 ] docked the compound trans 2-(aminomethyl)-4-oxazol-5-yl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] hydrogen sulfate (CPD4) against PBP2 of Escherichia coli and reported that CPD4 could be a potential scaffold for the development of active molecules which would be effective against a broad range of bacterial species.…”

Section: Resultsmentioning

confidence: 99%

Investigation of Plant Antimicrobial Peptides against Selected Pathogenic Bacterial Species Using a Peptide-Protein Docking Approach

Mustafa

Mehmood

Mahrosh

et al. 2022

BioMed Research International

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Antimicrobial resistance is the key threat to global health due to high morbidity and mortality. The alteration of bacterial proteins, enzymatic degradation, and change of membrane permeability towards antimicrobial agents are the key mechanisms of antimicrobial resistance. Based on the current condition, there is an urgent clinical need to develop new drugs to treat these bacterial infections. In the current study, the binding patterns of selected antimicrobial peptides (AMPs) with different multidrug-resistant bacterial strains have been analyzed. Among ten selected AMPs in this study, napin and snakin-1 exhibited the best scores and binding patterns. Napin exhibited strong interactions with penicillin-binding protein 1a of Acinetobacter baumannii (with a binding score of -158.7 kcal/mol and ten hydrogen bonds), with glucose-1-phosphate thymidylyltransferase of Mycobacterium tuberculosis H37Rv (with a binding score of -107.8 kcal/mol and twelve hydrogen bonds), and with streptomycin 3 ″ -adenylyltransferase protein of Salmonella enterica (with a binding score of -84.2 kcal/mol and four hydrogen bonds). Similarly, snakin-1 showed strong interactions with oxygen-insensitive NADPH nitroreductase of Helicobacter pylori (with a binding score of -105.0 kcal/mol and thirteen hydrogen bonds) and with penicillin-binding protein 2a of methicillin-resistant Staphylococcus aureus (with a binding score of -103.8 kcal/mol and twenty-three hydrogen bonds). The docking results were further validated by molecular dynamics simulations. The results of this computational approach support the evidence of efficiency of these AMPs as potent inhibitors of these specific proteins of bacterial strains. However, further validations are required to fully evaluate the potential of selected AMPs as drug candidates against these resistant bacterial strains.

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“…Nowadays, organic compounds are explored as potential candidates for NLO application due to their low cost and large nonlinear response . NLO is helpful in frequency shifting optical modulation, optical logic, optical switching, and optical memory in areas like telecommunications, optical interconnections, and signal processing. − Electronic properties are considered to be responsible for the strength of optical response, which in turn depends on the total molecular dipole moment (μ), linear response (polarizability, α), and nonlinear responses (hyperpolarizabilities, β, γ, etc. ). − The synthesized compounds CPFH, BCPH, and CCPH were studied at the CAM-B3LYP/6-311G (d,p) level for the evaluation of their NLO behavior.…”

Section: Results and Discussion (Computational)mentioning

confidence: 99%

An Experimental and Computational Exploration on the Electronic, Spectroscopic, and Reactivity Properties of Novel Halo-Functionalized Hydrazones

et al. 2020

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Herein, halo-functionalized hydrazone derivatives “2-[(6′-chloroazin-2′-yl)oxy]- N ′-(2-fluorobenzylidene) aceto-hydrazone ( CPFH ), 2-[(6′-chloroazin-2′-yl)oxy]- N ′-(2-chlorobenzylidene) aceto-hydrazones ( CCPH ), 2-[(6′-chloroazin-2′-yl)oxy]- N ′-(2-bromobenzylidene) aceto-hydrazones ( BCPH )” were synthesized and structurally characterized using FTIR, 1 H-NMR, 13 C-NMR, and UV–vis spectroscopic techniques. Computational studies using density functional theory (DFT) and time dependent DFT at CAM-B3LYP/6-311G (d,p) level of theory were performed for comparison with spectroscopic data (FT-IR, UV–vis) and for elucidation of the structural parameters, natural bond orbitals (NBOs), natural population analysis, frontier molecular orbital (FMO) analysis and nonlinear optical (NLO) properties of hydrazones derivatives ( CPFH , CCPH , and BCPH ). Consequently, an excellent complement between the experimental data and the DFT-based results was achieved. The NBO analysis confirmed that the presence of hyper conjugative interactions was pivotal cause for stability of the investigated compounds. The energy gaps in CPFH , CCPH , and BCPH were found as 7.278, 7.241, and 7.229 eV, respectively. Furthermore, global reactivity descriptors were calculated using the FMO energies in which global hardness revealed that CPFH was more stable and less reactive as compared to BCPH and CCPH . NLO findings disclosed that CPFH , CCPH , and BCPH have superior properties as compared to the prototype standard compound, which unveiled their potential applications for optoelectronic technology.

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Experimental and computational approaches of a novel methyl (2E)-2-{[N-(2-formylphenyl)(4-methylbenzene)sulfonamido]methyl}-3-(4-chlorophenyl)prop-2-enoate: A potential antimicrobial agent and an inhibition of penicillin-binding protein

Cited by 20 publications

References 87 publications

Exploration of N‐(6‐Indazolyl) benzenesulfonamide Derivatives as Potential Antioxidants and Antimicrobial Agents: Integrating Synthesis, In Silico Docking, and Bioactivity Profiling

Exploration of N‐(6‐Indazolyl) benzenesulfonamide Derivatives as Potential Antioxidants and Antimicrobial Agents: Integrating Synthesis, In Silico Docking, and Bioactivity Profiling

Investigation of Plant Antimicrobial Peptides against Selected Pathogenic Bacterial Species Using a Peptide-Protein Docking Approach

An Experimental and Computational Exploration on the Electronic, Spectroscopic, and Reactivity Properties of Novel Halo-Functionalized Hydrazones

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