Tailor made biheterocyclic pyrazoline-thiazolidinones as effective inhibitors of Escherichia coli FabH: Design, synthesis and structural studies

Salian, Vinutha V.; Narayana, B.; Sarojini, B. K.; Kumar, Mohit; Chandra, K. Sharath; Lobo, Anupam Glorious

doi:10.1016/j.molstruc.2019.04.105

Cited by 14 publications

(5 citation statements)

References 32 publications

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“…Salian et al., (2019) reported that compounds having −OCH 3 group on the benzene ring bind the active site more firmly. Similarly, this report presented that the target protein (FabH with PDB code; 5BNS) of E. coli has good interaction due to the presence of the methoxy group [56] . Hammad et al., (2020) reported that excellent anti‐bacterial activity was revealed by the compounds having the phenyl group with the substitution of m ‐OCH3, p ‐OH, and cyclohexyl groups [57] …”

Section: α‐Glucosidasementioning

confidence: 78%

“…Similarly, this report presented that the target protein (FabH with PDB code; 5BNS) of E. coli has good interaction due to the presence of the methoxy group. [56] Hammad et al, (2020) reported that excellent anti-bacterial activity was revealed by the compounds having the phenyl group with the substitution of m-OCH3, p-OH, and cyclohexyl groups. [57] In the D6 compound, Arg159 showed SÀ H interaction with the sulfur atom of thiazolidinone rings while Arg327 depicted hydrogen bonding with the methoxy and hydroxy oxygen atom of the compound and pi donor interaction with the sixmembered ring.…”

Section: α-Glucosidasementioning

confidence: 99%

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Designing of Thiazolidinones for COVID‐19 and its Allied Diseases: An In silico Evaluation

et al. 2022

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In silico studies in terms of density functional theory (DFT), molecular docking, and ADMET (absorption, distribution, metabolism, excretion and toxicity) were performed for 55 thiazolidinones compounds derived from different amines and aldehydes. DFT is a computational quantum mechanical modeling method used to predict the various properties of the compounds. Different parameters such as Electronegativity (x), Chemical Hardness (ŋ), Chemical Potential (μ), Ionization potential (IP), and Electron Affinity (EA), etc. were calculated by Koopmans theorem. The compounds were docked with Molecular Operating Environment (MOE) software using already reported PDB files of BChE, AChE, and α-glucosidase. To analyze the Spike Glycoprotein of SARS-Cov-2 and heterocyclic compounds, molecular interactions study was carried out between Spike Glycoprotein of SARS-Cov-2 (6VXX) and 55 synthetic heterocyclic compounds. It was performed by the utilization of PyRx Virtual Screening Tool and AutoDock Vina based virtual environment was used in PyRx. Maximum binding affinity was observed with compound A7 which was À 8.7 kcal/ mol and then with A5 which was À 8.5 respectively. In the case of the AChE enzyme, B5 has a maximum docking score of À 12.9027 kcal/mol while C7 depicted the maximum score for the BChE enzyme with a value of À 8.6971 kcal/mol. The docking studies revealed that C6 compound has maximum binding capacity toward glucosidase (À 14.8735 kcal/mol). ADMET properties of under consideration compounds were determined by Swiss online-based software which concluded that these molecules have a drug-like properties and having no violation.

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Section: α‐Glucosidasementioning

confidence: 78%

Section: α-Glucosidasementioning

confidence: 99%

Designing of Thiazolidinones for COVID‐19 and its Allied Diseases: An In silico Evaluation

et al. 2022

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“…The 2D fingerprint plots derived from Hirshfeld analysis are set up by plotting d e against d i . The d norm , which is the normalized contact distance, is based on van der Waals radii of the atom, d i and d e 67 . Each point is displayed on a 2D grid according to the fraction of the total surface area contained in a given data bin.…”

Section: Resultsmentioning

confidence: 99%

A facile synthesis of pyrano[2,3‐d:6,5‐d′]dipyrimidines via microwave‐assisted multicomponent reactions catalyzed by β‐cyclodextrin

Jayashree

Narayana

Kunhanna

et al. 2020

Journal of Heterocyclic Chem

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A facile three‐component reaction of aromatic aldehyde, 2,2‐dimethyl‐1,3‐dioxane‐4,6‐dione, and 6‐amino‐1,3‐dimethyluracil was developed for the first time using β‐cyclodextrin (β‐CD) as a macrocyclic host for aldehyde and an efficient catalyst that leads to a batch of novel pyrano[2,3‐d:6,5‐d′]dipyrimidines (4a‐k). The synthesis was accomplished with the aid of microwave irradiations in solvent‐free conditions. The product obtained was in contrast to the previous report in which a similar reaction resulted in a mixture of benzylidenepyrimidine and bisaminopyrimidine analogs in the presence of triethylbenzylammonium chloride in an aqueous medium. The formation of the pyrano[2,3‐d:6,5‐d′]dipyrimidines may be in virtue of the property of β‐CD to construct new CC and CX (where X = heteroatom) bonds. Reusability of the catalyst up to three runs without any noteworthy change in catalytic activity is one of the main features of the reaction. Other noteworthy features are good to excellent yields, eco‐friendly procedure, non‐column chromatographic purification, and mild conditions.

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“…6 The inhibitory activity of L against bacterial growth is believed to be due to its ability to target the FabH enzyme, which is essential for the biosynthesis of fatty acids in bacteria. 7 The compound binds to the active site of FabH and inhibits its activity, thereby preventing the production of fatty acids and disrupting bacterial growth.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structures and Antibacterial Activity of Nickel(II) and Copper(II) Complexes Derived from (E)-2-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methylene)- N-phenylhydrazinecarbothioamide

Wang,

Fei,

Zhou

et al. 2024

ACSi

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The biosynthesis of fatty acids is essential for the survival of bacteria, and β-ketoacyl-acyl carrier protein synthase III (FabH) is a promising target for antibacterial drug development. Nickel(II) complex [NiL2] (1) and copper(II) complex [CuL2] (2), where L is (E)-2-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methylene)-N-phenylhydrazinecarbothioamide, were synthesized and characterized by elemental analysis, IR and 1H NMR spectroscopy and HRMS. Structures of the complexes were further studied by single crystal X-ray determination, which reveals that the nickel and copper atoms in the complexes are in tetrahedral geometry. These compounds were evaluated for their antibacterial and E. coli FabH inhibitory activities.

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Tailor made biheterocyclic pyrazoline-thiazolidinones as effective inhibitors of Escherichia coli FabH: Design, synthesis and structural studies

Cited by 14 publications

References 32 publications

Designing of Thiazolidinones for COVID‐19 and its Allied Diseases: An In silico Evaluation

Designing of Thiazolidinones for COVID‐19 and its Allied Diseases: An In silico Evaluation

A facile synthesis of pyrano[2,3‐d:6,5‐d′]dipyrimidines via microwave‐assisted multicomponent reactions catalyzed by β‐cyclodextrin

Synthesis, Crystal Structures and Antibacterial Activity of Nickel(II) and Copper(II) Complexes Derived from (E)-2-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methylene)- N-phenylhydrazinecarbothioamide

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