Designing and synthesis of novel antimicrobial heterocyclic analogs of fatty acids

Ahmad, Afaq; Ahmad, Anis; Varshney, Himani; Rehan, Mohd; Subbarao, Naidu; Khan, Asad U.

doi:10.1016/j.ejmech.2013.10.051

Cited by 29 publications

(11 citation statements)

References 49 publications

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“…Five membered heterocyclic compounds, particularly those having the pyrazole and isoxazole frameworks, are components of a diverse array of compounds with a broad spectrum of bioactivities such as analgesic, [1][2][3] anti-inflammatory [3][4][5], antibacterial [3,6,7], antifungal [3,8,9], antitumoral [3,10,11] and antiviral [3,12,13] activities.…”

Section: Introductionmentioning

confidence: 99%

Unveiling the Different Chemical Reactivity of Diphenyl Nitrilimine and Phenyl Nitrile Oxide in [3+2] Cycloaddition Reactions with (R)-Carvone through the Molecular Electron Density Theory

Ríos‐Gutiérrez

Domingo

Esseffar³

et al. 2020

Molecules

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The [3+2] cycloaddition (32CA) reactions of diphenyl nitrilimine and phenyl nitrile oxide with (R)-carvone have been studied within the Molecular Electron Density Theory (MEDT). Electron localisation function (ELF) analysis of these three-atom-components (TACs) permits its characterisation as carbenoid and zwitterionic TACs, thus having a different reactivity. The analysis of the conceptual Density Functional Theory (DFT) indices accounts for the very low polar character of these 32CA reactions, while analysis of the DFT energies accounts for the opposite chemoselectivity experimentally observed. Topological analysis of the ELF along the single bond formation makes it possible to characterise the mechanisms of these 32CA reactions as cb- and zw-type. The present MEDT study supports the proposed classification of 32CA reactions into pdr-, pmr-, cb- and zw-type, thus asserting MEDT as the theory able to explain chemical reactivity in Organic Chemistry.

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Section: Introductionmentioning

confidence: 99%

Unveiling the Different Chemical Reactivity of Diphenyl Nitrilimine and Phenyl Nitrile Oxide in [3+2] Cycloaddition Reactions with (R)-Carvone through the Molecular Electron Density Theory

Ríos‐Gutiérrez

Domingo

Esseffar³

et al. 2020

Molecules

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“…For example, E . coli S12 was used for in silico screening to predict the binding modes of heterocyclics, such as, pyrazolone and oxazolones, and to compare their binding properties with ciprofloxacin (positive control) (Shamsuzzaman et al, 2014[22]; Ahmad et al, 2013[1]). Accordingly, to predict the binding mode of MBA-dMPP, in silico docking studies were conducted on its binding to the ciprofloxacin binding site.…”

Section: Resultsmentioning

confidence: 99%

Physicochemical analyses of a bioactive 4-aminoantipyrine analogue - synthesis, crystal structure, solid state interactions, antibacterial, conformational and docking studies

Alam

Lee

2016

EXCLI Journal; 15:Doc614; ISSN 1611-2156

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“…The integrity of a fungal cell is provided by its plasma membrane, therefore insertion of fatty acids into bilayer can physically disrupt it and increase the fluidity [ 21 ]. Fatty acid derivatives containing heterocyclic moieties also tend to be biologically beneficial in combating microorganisms [ 22 , 23 ]. It is important to evaluate the antibacterial and antifungal effect of these five-membered heterocyclic compounds containing long alkyl chain as they show versatile pharmacological and biological activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structural Studies and Biological Evaluation of Connections of Thiosemicarbazide, 1,2,4-Triazole and 1,3,4-Thiadiazole with Palmitic Acid

et al. 2018

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Thirty new derivatives of palmitic acid were efficiently synthesized. All obtained compounds can be divided into three groups of derivatives: Thiosemicarbazides (compounds 1–10), 1,2,4-triazoles (compounds 1a–10a) and 1,3,4-thiadiazoles (compounds 1b–10b) moieties. 1H-NMR, 13C-NMR and MS methods were used to confirm the structure of derivatives. All obtained compounds were tested in vitro against a number of microorganisms, including Gram-positive cocci, Gram-negative rods and Candida albicans. Compounds 4, 5, 6, 8 showed significant inhibition against C. albicans. The range of MIC values was 50–1.56 μg/mL. The halogen atom, especially at the 3rd position of the phenyl group was significantly important for antifungal activity. The biological activity against Candida albicans and selected molecular descriptors were used as a basis for QSAR models, that have been determined by means of multiple linear regression. The models have been validated by means of the Leave-One-Out Cross Validation. The obtained QSAR models were characterized by high determination coefficients and good prediction power.

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Designing and synthesis of novel antimicrobial heterocyclic analogs of fatty acids

Cited by 29 publications

References 49 publications

Unveiling the Different Chemical Reactivity of Diphenyl Nitrilimine and Phenyl Nitrile Oxide in [3+2] Cycloaddition Reactions with (R)-Carvone through the Molecular Electron Density Theory

Unveiling the Different Chemical Reactivity of Diphenyl Nitrilimine and Phenyl Nitrile Oxide in [3+2] Cycloaddition Reactions with (R)-Carvone through the Molecular Electron Density Theory

Physicochemical analyses of a bioactive 4-aminoantipyrine analogue - synthesis, crystal structure, solid state interactions, antibacterial, conformational and docking studies

Synthesis, Structural Studies and Biological Evaluation of Connections of Thiosemicarbazide, 1,2,4-Triazole and 1,3,4-Thiadiazole with Palmitic Acid

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