3D-QSAR modeling, molecular docking and ADMET properties of benzothiazole derivatives as α-glucosidase inhibitors

Khaldan, Ayoub; Bouamrane, Soukaina; El-Mernissi, Reda; Maghat, Hamid; Ajana, Mohammed Aziz; Sbai, Abdelouahid; Bouachrine, Mohammed; Lakhlifi, Tahar

doi:10.1016/j.matpr.2021.03.114

Cited by 11 publications

(10 citation statements)

References 34 publications

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“…The regions greatly impact the activity of the molecules in 3D space, creating an opportunity to suggest new compounds that are more effective than the current molecules in the database. 81 Molecule C3 represents the contour maps because it has the highest activity value (Fig. 9).…”

Section: Results and Analysismentioning

confidence: 99%

Computational approach: 3D-QSAR, molecular docking, ADMET, molecular dynamics simulation investigations, and retrosynthesis of some curcumin analogues as PARP-1 inhibitors targeting colon cancer

Zrinej,

Elmchichi,

Alaqarbeh

et al. 2023

New J. Chem.

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Section: Results and Analysismentioning

confidence: 99%

Computational approach: 3D-QSAR, molecular docking, ADMET, molecular dynamics simulation investigations, and retrosynthesis of some curcumin analogues as PARP-1 inhibitors targeting colon cancer

Zrinej,

Elmchichi,

Alaqarbeh

et al. 2023

New J. Chem.

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“…The solubility of a medication in water is a property used in the medication development process to determine whether or not a medication is soluble in water, and its value is given in log(mol L −1 ). 22,77 Table 9 reveals that the five studied quinoline-based thiadiazole derivatives are water soluble. Absorption is the initial step in the drug action process, and it can be defined as the medication's journey from administration to effect.…”

Section: Resultsmentioning

confidence: 99%

“…Its primary aim is to predict the clinical success of medicine candidates, as inadequate bioavailability is estimated to cause 50% of therapeutic failures. 21,22…”

Section: Introductionmentioning

confidence: 99%

Computational study of quinoline-based thiadiazole compounds as potential antileishmanial inhibitors

et al. 2022

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“…Fortunately, our candidate compounds 2-(3,5-dihydroxyphenyl)-5,7-dihydroxy-4 H -chromen-4-one and norartocarpetin are not expected to show toxicity to cancerous rat and mouse cells. As shown in Table S3 , based on drug similarity predictions, the natural compounds conformed to Lipinski’s rule, Veber’s rule, and Egan’s rule, indicating that the compounds can be easily synthesized [ 51 ]. Thus, these studies provide favorable support for our model to predict the outcomes of natural α-glucosidase inhibitors.…”

Section: Resultsmentioning

confidence: 99%

Construction of an MLR-QSAR Model Based on Dietary Flavonoids and Screening of Natural α-Glucosidase Inhibitors

Yang

Pan

et al. 2022

Foods

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Postprandial hyperglycemia can be reduced by inhibiting α-glucosidase activity. Common α-glucosidase inhibitors such as acarbose may have various side effects. Therefore, it is important to find natural products that are non-toxic and have high α-glucosidase-inhibitory activity. In the present study, a comprehensive computational analysis of 27 dietary flavonoid compounds with α-glucosidase-inhibitory activity was performed. These included flavonoids, flavanones, isoflavonoids, dihydrochalcone, flavan-3-ols, and anthocyanins. Firstly, molecular fingerprint similarity clustering analysis was performed on the target molecules. Secondly, multiple linear regression quantitative structure–activity relationship (MLR-QSAR) models of dietary flavonoids (2D descriptors and 3D descriptors optimized), with R2 of 0.927 and 0.934, respectively, were constructed using genetic algorithms. Finally, the MolNatSim tool based on the COCONUT database was used to match the similarity of each flavonoid in this study, and to sequentially perform molecular enrichment, similarity screening, and QSAR prediction. After screening, five kinds of natural product molecule (2-(3,5-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one, norartocarpetin, 2-(2,5-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one, 2-(3,4-dihydroxyphenyl)-5-hydroxy-4H-chromen-4-one, and morelosin) were finally obtained. Their IC50pre values were 8.977, 31.949, 78.566, 87.87, and 94.136 µM, respectively. Pharmacokinetic predictions evaluated the properties of the new natural products, such as bioavailability and toxicity. Molecular docking analysis revealed the interaction of candidate novel natural flavonoid compounds with the amino acid residues of α-glucosidase. Molecular dynamics (MD) simulations and molecular mechanics/generalized Born surface area (MMGBSA) further validated the stability of these novel natural compounds bound to α-glucosidase. The present findings may provide new directions in the search for novel natural α-glucosidase inhibitors.

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3D-QSAR modeling, molecular docking and ADMET properties of benzothiazole derivatives as α-glucosidase inhibitors

Cited by 11 publications

References 34 publications

Computational approach: 3D-QSAR, molecular docking, ADMET, molecular dynamics simulation investigations, and retrosynthesis of some curcumin analogues as PARP-1 inhibitors targeting colon cancer

Computational approach: 3D-QSAR, molecular docking, ADMET, molecular dynamics simulation investigations, and retrosynthesis of some curcumin analogues as PARP-1 inhibitors targeting colon cancer

Computational study of quinoline-based thiadiazole compounds as potential antileishmanial inhibitors

Construction of an MLR-QSAR Model Based on Dietary Flavonoids and Screening of Natural α-Glucosidase Inhibitors

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