Synthesis of new halogenated flavonoid-based isoxazoles: in vitro and in silico evaluation of a-amylase inhibitory potential, a SAR analysis and DFT studies

Saidi, Ilyes; Manachou, Marwa; Znati, Mansour; Bouajila, Jalloul; Jannet, Hichem Ben

doi:10.1016/j.molstruc.2021.131379

Cited by 24 publications

(13 citation statements)

References 79 publications

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“…However, this ligand showed a dipole-dipole interaction via its Cl atom with Asp340 residue, while an arene-H interaction was also found with the residue His296. In a recent report, flavonoid-based isoxazoles also showed interactions with the same type of residues during in silico screening against α-amylase enzyme [65]. The ligand 12d exhibited two interactions with the residue Asp340 using its NH and nitrophenyl group.…”

Section: α-Amylase (Molecular Docking)mentioning

confidence: 94%

“…The molecular docking studies of the 1,2-benzothiazine derivatives against the Aspergillus oryzae α-amylase (PDB ID: 7TAA) [65,66] were found effective, as some of the derivatives showed the best docking scores (−14.60 to −16.13 Kcal/mol), which were comparable to the docking score of the standard drug, acarbose (−17.69 Kcal/mol) (Table 1). In addition, these scaffolds also demonstrated excellent binding interactions with the selected residues (Trp83, Asp340, Arg344, Arg204, Glu230, Lys209) (Figure 3) and low RMSD values (Table 1).…”

Section: α-Amylase (Molecular Docking)mentioning

confidence: 99%

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Identification of Cyclic Sulfonamides with an N-Arylacetamide Group as α-Glucosidase and α-Amylase Inhibitors: Biological Evaluation and Molecular Modeling

et al. 2022

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Diabetes mellitus (DM), a complicated metabolic disorder, is due to insensitivity to insulin function or reduction in insulin secretion, which results in postprandial hyperglycemia. α-Glucosidase inhibitors (AGIs) and α-amylase inhibitors (AAIs) block the function of digestive enzymes, which delays the carbohydrate hydrolysis process and ultimately helps to control the postprandial hyperglycemia. Diversified 2-(3-(3-methoxybenzoyl)-4-hydroxy-1,1-dioxido-2H-benzo[e][1,2]thiazin-2-yl)-N-arylacetamides were synthesized and evaluated for their in vitro inhibitory potential against α-glucosidase and α-amylase enzymes. The compounds with chloro, bromo and methyl substituents demonstrated good inhibition of α-glucosidase enzymes having IC50 values in the range of 25.88–46.25 μM, which are less than the standard drug, acarbose (IC50 = 58.8 μM). Similarly, some derivatives having chloro, bromo and nitro substituents were observed potent inhibitors of α-amylase enzyme, with IC50 values of 7.52 to 15.06 μM, lower than acarbose (IC50 = 17.0 μM). In addition, the most potent compound, N-(4-bromophenyl)-2-(4-hydroxy-3-(3-methoxybenzoyl)-1,1-dioxido-2H-benzo[e][1,2]thiazin-2-yl)acetamide (12i), was found to be a non-competitive and competitive inhibitor of α-glucosidase and α-amylase enzymes, respectively, during kinetic studies. The molecular docking studies provided the binding modes of active compounds and the molecular dynamics simulation studies of compound 12i in complex with α-amylase also showed that the compound is binding in a fashion similar to that predicted by molecular docking studies.

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Section: α-Amylase (Molecular Docking)mentioning

confidence: 94%

Section: α-Amylase (Molecular Docking)mentioning

confidence: 99%

Identification of Cyclic Sulfonamides with an N-Arylacetamide Group as α-Glucosidase and α-Amylase Inhibitors: Biological Evaluation and Molecular Modeling

et al. 2022

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“…Enzyme inhibitors are bioactive molecules capable of inhibiting or limiting the natural functioning of target enzymes by occupying their active pocket and competing with the substrate, 28,31 or by occupying distant allosteric sites. Indeed, the binding energy reects the stability of the molecule-enzyme complex.…”

Section: Molecular Docking Analysismentioning

confidence: 99%

Semi-synthesis, α-amylase inhibition, and kinetic and molecular docking studies of arylidene-based sesquiterpene coumarins isolated from Ferula tunetana Pomel ex Batt

Baccari,

Saidi,

Filali

et al. 2024

RSC Adv.

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“…Among them, compound 52 ( Figure 39 ) (IC 50 = 16.2 ± 0.3 µM) exhibited the highest anti-α-amylase activity comparable to the standard (acarbose, IC 50 = 15.7 ± 0.2 µM). An SAR analysis revealed that bromine atoms are essential for α-amylase inhibitory activity [ 76 ].…”

Section: Biological Effects Of Natural Products Containing the Isoxaz...mentioning

confidence: 99%

Isoxazole/Isoxazoline Skeleton in the Structural Modification of Natural Products: A Review

Wang

Tang

et al. 2023

Pharmaceuticals

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Isoxazoles and isoxazolines are five-membered heterocyclic molecules containing nitrogen and oxygen. Isoxazole and isoxazoline are the most popular heterocyclic compounds for developing novel drug candidates. Over 80 molecules with a broad range of bioactivities, including antitumor, antibacterial, anti-inflammatory, antidiabetic, cardiovascular, and other activities, were reviewed. A review of recent studies on the use of isoxazoles and isoxazolines moiety derivative activities for natural products is presented here, focusing on the parameters that affect the bioactivity of these compounds.

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Synthesis of new halogenated flavonoid-based isoxazoles: in vitro and in silico evaluation of a-amylase inhibitory potential, a SAR analysis and DFT studies

Cited by 24 publications

References 79 publications

Identification of Cyclic Sulfonamides with an N-Arylacetamide Group as α-Glucosidase and α-Amylase Inhibitors: Biological Evaluation and Molecular Modeling

Identification of Cyclic Sulfonamides with an N-Arylacetamide Group as α-Glucosidase and α-Amylase Inhibitors: Biological Evaluation and Molecular Modeling

Semi-synthesis, α-amylase inhibition, and kinetic and molecular docking studies of arylidene-based sesquiterpene coumarins isolated from Ferula tunetana Pomel ex Batt

Isoxazole/Isoxazoline Skeleton in the Structural Modification of Natural Products: A Review

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