Synthesis, experimental antimicrobial activity, theoretical vibrational analysis, quantum chemical modeling and molecular docking studies of (E)-4-(benzylideneamino)benzenesulfonamide

Muthukumar, R.; Karnan, M.; Elangovan, N.; Karunanidhi, M.; Sankarapandian, Vidya; Venkateswaran, K.

doi:10.1016/j.molstruc.2022.133187

Cited by 41 publications

(5 citation statements)

References 63 publications

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“…Since the space between the orbitals is smaller, the compound is highly reactive and unstable. [ 50 ] The calculated band gap occurring in the gas phase was 3.54 eV. [ 51 ] Due to the charge transfer between molecules, the pharmacological activity of a compound enhances when its HOMO‐LUMO energy gap is lowered.…”

Section: Resultsmentioning

confidence: 99%

“…The colour‐coded maps representing intra‐ and intermolecular attractive and repulsive forces ecan be obtained from the lectron density against molecule‐specific Hessian plots. [ 50 ] RDG maps were prepared with the assistance of Multiwfn 3.8 software inorder to illustrate weak interaction. The red areas represent the region where the steric effect is prevalent, while the green depict the region where van der Waals interactions are minimal.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, spectral features, electronic structure studies, and molecular docking analysis of a Schiffbase (E)‐1‐(4‐chlorophenyl)‐N‐(nitrophenyl)methanimine from 4‐chloroaniline and 2‐nitrobenzaldehyde

Diya,

Unni,

Rajimon

et al. 2023

Vietnam Journal of Chemistry

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The compound (E)‐1‐(4‐chlorophenyl)‐N‐(nitrophenyl)methanimine was synthesised and characterised using techniques FTIR, UV‐Vis, NMR and it was compared with the experimental and simulated methods. The compound prepared was optimized using the DFT method employing the basis set B3LYP / cc‐pVDZ. The simulated spectra appeared to be in accordance with the experimental one. The HOMO‐LUMO orbitals and MEP are calculated with the same basis set; the study is chiefly forcasted to the biological activity of the synthesized compound. The wave function regards like localized orbital locator, electron localized function, average localized ionization energy and non‐covalent interaction are also examined as a means of theoretical evidence of the titled compound. The NBO calculations probe the intermolecular and intramolecular movement of charges, and additionally the molecule's stability. The ADMET properties are also considered for the compound with the assistance of Swiss ADMET online tool. The molecular docking analysis was accomplished against the protein (3RW9) of Spermidine dehydrogenase inhibitor employing the software Auto‐dock.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis, spectral features, electronic structure studies, and molecular docking analysis of a Schiffbase (E)‐1‐(4‐chlorophenyl)‐N‐(nitrophenyl)methanimine from 4‐chloroaniline and 2‐nitrobenzaldehyde

Diya,

Unni,

Rajimon

et al. 2023

Vietnam Journal of Chemistry

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“…and Sajia Islam et al . have also explored the pharmacokinetic properties of the drugs under consideration by employing the similar approach [ 70 , 71 ]. Afterwards, we also calculated five major factors regarding the pharmacokinetics of cinnamyl acetate and benzyl benzoate .…”

Section: Discussionmentioning

confidence: 99%

“…However, the ADMET analysis presented by Qaddir et al while investigating different phytochemicals as potential dengue virus inhibitors, were significantly appreciable [69]. R. Muthukumar et al and Sajia Islam et al have also explored the pharmacokinetic properties of the drugs under consideration by employing the similar approach [70,71]. Afterwards, we also calculated five major factors regarding the pharmacokinetics of cinnamyl acetate and benzyl benzoate.…”

Section: Plos Onementioning

confidence: 97%

Assessing the efficacy of cinnamon compounds against H. pylori through molecular docking, MD Simulations and ADMET analyses

Sarwar,

Zahra,

Awan

et al. 2024

PLoS ONE

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Antibiotics are the drugs that are used for the management of microbial diseases. However, these conventional synthetic drugs can harmfully affect the human health. Since phytochemicals are extracted from natural sources and, are hence relatively safer for human health, they are the enticing alternatives in this regard. Cinnamon is also one of those plants which is being employed as herbal medication for centuries against certain microbial infections due its significant therapeutic effectiveness. A well-known pathogenic bacterium called H. pylori causes a wide range of illnesses in human body. This pathogen’s pathogenicity is determined by certain virulent proteins. In this study, some of such proteins, which included virB4, virB8, and virB9 were selected to evaluate the therapeutic efficiency of cinnamon compounds. These proteins were identified in different isolates of H. pylori. The structural modelling of all these proteins were performed initially in order to proceed them for molecular docking analysis. While, the docking studies illustrated that one of the cinnamon compounds, cinnamyl acetate, showed significant binding interactions with virB4 and virB9. However, benzyl benzoate which is another cinnamon compound, docked well with virB8. Afterwards, the MD simulations were incorporated to explore the interaction motions and structural stability of all the docked complexes. In this regard, the resultant maps of Bfactor, eigenvalues and elastic network model, among other factors ensured the structural stabilities of all the respective complexes. After these crucial estimations, benzyl benzoate and cinnamyl acetate underwent the ADMET investigation to assess their pharmacokinetic characteristics. SwissADME and ADMETLab 2.0 server were employed for this investigation. The compiled findings these servers revealed that both, benzyl benzoate and cinnamyl acetate, exhibited a significant level of pharmacokinetic and drug-likeness conformity.

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“…[28] Benzenesulfonamide is another inescapable motif in medicinal chemistry owing to its high potential as an antimicrobial agent and plays a crucial role in the synthesis of antimicrobial drugs. [29][30][31][32] The underlying reason for the high antibacterial potential of benzenesulfonamide lies in its structural similarity with para-aminobenzoic acid (PABA), causing interference in the process of folate synthesis, a key step for DNA and RNA synthesis in bacterial cells. [33] Furthermore, benzenesulfonamides are highly selective for bacterial cells only as human cells do not synthesize folate similar to bacteria.…”

mentioning

confidence: 99%

Synthesis and biological evaluation of novel benzenesulfonamide incorporated thiazole–triazole hybrids as antimicrobial and antioxidant agents

Monika,

Chander,

Sharma

et al. 2023

Archiv der Pharmazie

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A library of 20 novel benzenesulfonamide incorporating thiazole tethered 1,2,3‐triazoles 1–4a–e was synthesized and screened for their antimicrobial, antioxidant, and cytotoxicity studies. Amoxicillin and fluconazole were used as reference antibacterial and antifungal drugs, respectively. Further, energies of frontier molecular orbitals were calculated for all the synthesized target compounds 1–4a–e to correlate electronic parameters with the observed biological results. Global reactivity descriptors, including highest occupied molecular orbitals‐lowest unoccupied molecular orbitals energy gap, electronegativity, chemical hardness, chemical softness, and electrophilicity index, were also calculated for the synthesized molecules. All the tested compounds possessed moderate to excellent antibacterial potency; however, 3d and 4d exhibited the overall highest antibacterial effect (minimum inhibitory concentration [MIC] values 5–11 µM) while 2c showed the highest antifungal effect (MIC value 6 µM). Compound 3c exhibited the highest antioxidant activity with a % radical scavenging activity value of 95.12. The cytotoxicity of the compounds 1–4a–e was also checked against an animal cell line and a plant seed germination cell line, and the compounds were found to be safe against both the tested cell lines.

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Synthesis, experimental antimicrobial activity, theoretical vibrational analysis, quantum chemical modeling and molecular docking studies of (E)-4-(benzylideneamino)benzenesulfonamide

Cited by 41 publications

References 63 publications

Synthesis, spectral features, electronic structure studies, and molecular docking analysis of a Schiffbase (E)‐1‐(4‐chlorophenyl)‐N‐(nitrophenyl)methanimine from 4‐chloroaniline and 2‐nitrobenzaldehyde

Synthesis, spectral features, electronic structure studies, and molecular docking analysis of a Schiffbase (E)‐1‐(4‐chlorophenyl)‐N‐(nitrophenyl)methanimine from 4‐chloroaniline and 2‐nitrobenzaldehyde

Assessing the efficacy of cinnamon compounds against H. pylori through molecular docking, MD Simulations and ADMET analyses

Synthesis and biological evaluation of novel benzenesulfonamide incorporated thiazole–triazole hybrids as antimicrobial and antioxidant agents

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