Design, synthesis, molecular docking and DFT computational insight on the structure of Piperazine sulfynol derivatives as a new antibacterial contender against superbugs MRSA

Prasad, H.S. Nagendra; Ananda, A.P.; Lohith, T.N.; Prabhuprasad, P.; Jayanth, H.S.; Krishnamurthy, N. B.; Sridhar, M. A.; Mallesha, L.; Mallu, P.

doi:10.1016/j.molstruc.2021.131333

Cited by 29 publications

(9 citation statements)

References 65 publications

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“…However, the change in the position of the chlorine atom from para to ortho in the Ar 1 moiety resulted in a significant decrease of the antibacterial effect of compound 6m (Ar = p -Cl(C 6 H 4 ), Ar 1 = o -Cl(C 6 H 4 )) against the same strain ( S. aureus ), which is consistent with other previously described studies on homologous compounds. 59 The decrease in bioactivity showed for compound 6m when compared to that of hybrid compound 6d may be related to unfavorable interactions of chlorine in the ortho-phenyl position, which prevents its ability to inhibit the S. aureus strain. The antimicrobial efficacy of the others target hybrids is also decreased when chlorine atom is replaced by other groups in the para position of the aromatic rings (Ar and Ar 1 ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, DFT Mechanistic Study, Antimicrobial Activity, Molecular Modeling, and ADMET Properties of Novel Pyrazole-isoxazoline Hybrids

et al. 2022

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A series of new heterocycle hybrids incorporating pyrazole and isoxazoline rings was successfully synthesized, characterized, and evaluated for their antimicrobial responses. The synthesized compounds were obtained utilizing N-alkylation and 1,3-dipolar cycloaddition reactions, as well as their structures were established through spectroscopic methods and confirmed by mass spectrometry. To get more light on the regioselective synthesis of new hybrid compounds, mechanistic studies were performed using DFT calculations with B3LYP/6-31G(d,p) basis set. Additionally, the results of the preliminary screening indicate that some of the examined hybrids showed potent antimicrobial activity, compared to standard drugs. The results confirm that the antimicrobial activity is strongly dependent on the nature of the substituents linked pyrazole and isoxazoline rings. Furthermore, molecular docking studies were conducted to highlight the interaction modes between the investigated hybrid compounds and the Escherichia coli and Candida albicans receptors. Notably, the results demonstrate that the investigated compounds have strong protein binding affinities. The stability of the formed complexes by the binding between the hybrid compound 6c, and the target proteins was also confirmed using a 100 ns molecular dynamics simulation. Finally, the prediction of ADMET properties suggests that almost all hybrid compounds possess good pharmacokinetic profiles and no signs of observed toxicity, except for compounds 6e, 6f, and 6g.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, DFT Mechanistic Study, Antimicrobial Activity, Molecular Modeling, and ADMET Properties of Novel Pyrazole-isoxazoline Hybrids

et al. 2022

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“…Molecular modeling of the compound was carried out by Gaussian 09 (Frisch et al, 2009) program using DFT/B3LYP (Prasad et al, 2022) density functional theory with 6-311G (Foresman & Frisch, 1996) base set and semi-emprical theory with AM1 (Austin Model 1) (Dewar et al, 1985) base set. HOMOs and LUMOs as frontier molecular orbitals computed by DFT method play a important role in the chemical reactivities, stabilities and electronic transition levels of molecules (Dennington et al, 2016).…”

Section: Computation Detailsmentioning

confidence: 99%

Design, DFT Calculations and Antimicrobial Activity of New Synthesized Piperazine Derivative

MUHAMMET>

2023

Gazi University Journal of Science Part A: Engineering and Innovation

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The title compound (2,2'-(piperazine-1,4-diyl)bis(N'-((E)-5-chloro-2-hydroxybenzylidene) acetohydrazide) (5-ClPAH) was synthesized by reacting 1,4-Piperazinediacetic acid, 1,4-dihydrazide and 5 -Chloro-2-hydroxybenzaldehyde. Mass spectrometry, 1H, 13C-NMR, IR results of the synthesized compound were examined. Many information about physical and chemical properties of 5-ClPAH can be obtained by theoretical calculations. Density functional theory (DFT) is widely used theoretical method for predicting of chemical structures. The structure was optimized using DFT/6311G method with GAUSSIAN09. Frontier Molecular Orbitls (HOMO and LUMO) energies were calculated. Global reactivity descriptors and also electrophilic and nucleophilic regions were defined by molecular electrostatic potential surface. Antibacterial and fungal activity were evaluated.

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“…In the present drug development, the potential of a novel chemical is commonly evaluated using initially through virtual tools [6]. The drug-likeness and ADME parameters of the pFPP molecule have been evaluated in order to determine its suitability for usage as an active substance in a variety of novel pharmaceutical products.…”

Section: Drug-likeness and Adme Analysismentioning

confidence: 99%

“…On the other hand, it is frequently employed to generate a variety of physiologically active compounds, including anticonvulsant, anxiolytic, neuroprotective, antioxidant, antidepressant, and anti-Alzheimer's [5]. A large number of well-known medications with a variety of uses contain piperazine, a six-membered heterocyclic molecule that contains nitrogen [6]. Due to their powerful biological activity and their involvement in the creation of promising pharmacological candidates, fluorinecontaining heterocyclic compounds have attracted considerable attention [7].…”

Section: Introductionmentioning

confidence: 99%

Conformational Analysis and DFT Investigations of 1-(4-Fluorophenyl)Piperazine by ELF and LOL, Inhibitory activity against Alzheimer’s Disease, and ADME Prediction

Celik

2022

Sakarya University Journal of Science

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This study reports 1-(4-Fluorophenyl)Piperazine molecule structural and electronic properties calculated at the DFT/B3LYP level. A potential energy surface scan along the rotational bonds discovered the most stable minimum energy conformer of the title compound. Frontier molecular orbitals (FMO) analyses, density of state (DOS), molecular electrostatic potential (MEP), and global and chemical reactivity descriptors were also used to investigate the reactivity of the pFPP molecule. In addition, ELF and LOL analysis were performed. In silico biological studies such as drug-likeness, ADME, and toxicity properties were also performed. Molecular docking studies are performed to predict the anti-Alzheimer agent enzyme (AChE) active site of the pFPP. The docking predicts the possibility of a potential drug to improve Alzheimer's disease (AD) treatment.

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Design, synthesis, molecular docking and DFT computational insight on the structure of Piperazine sulfynol derivatives as a new antibacterial contender against superbugs MRSA

Cited by 29 publications

References 65 publications

Synthesis, Characterization, DFT Mechanistic Study, Antimicrobial Activity, Molecular Modeling, and ADMET Properties of Novel Pyrazole-isoxazoline Hybrids

Synthesis, Characterization, DFT Mechanistic Study, Antimicrobial Activity, Molecular Modeling, and ADMET Properties of Novel Pyrazole-isoxazoline Hybrids

Design, DFT Calculations and Antimicrobial Activity of New Synthesized Piperazine Derivative

Conformational Analysis and DFT Investigations of 1-(4-Fluorophenyl)Piperazine by ELF and LOL, Inhibitory activity against Alzheimer’s Disease, and ADME Prediction

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