Design, synthesis, and <i>in vitro</i> and <i>in silico</i> studies of 1,3,4-thiadiazole-thiazolidinone hybrids as carbonic anhydrase inhibitors

Nasab, Narges Hosseini; Raza, Hussain; Eom, Young Seok; Hassan, Mubashir; Kloczkowski, Andrzej; Chetty, Lloyd Christopher.; Kruger, Hendrik G.; Kim, Song Ja

doi:10.1039/d3nj01547e

Cited by 5 publications

(2 citation statements)

References 66 publications

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“…The main goal of this method is to integrate two or more different pharmacophore moieties into a single molecule with a common scaffold, which may have more advantages over standard drugs. Our research team is persistently engaged in the design and synthesis of diverse heterocyclic scaffolds to explore potent therapeutic and inhibitors options [42][43][44][45][46]. Therefore, in our present research, we are combining the three biologically significant moieties of chalcone, sulfonyl, and piperazine utilizing molecular hybridization to create new hybrid compounds that are effective alpha-amylase and alpha-glucosidase inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Exploring chalcone-sulfonyl piperazine hybrids as anti-diabetes candidates: design, synthesis, biological evaluation, and molecular docking study

Hosseini Nasab,

Raza,

Eom

et al. 2024

Mol Divers

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To combat the rising rates of diabetes mellitus over the world, novel compounds are required. The demand for more affordable and efficient methods of managing diabetes is increasing due to the unavoidable side effects associated with the existing antidiabetic medications. In order to develop inhibitors against alpha-glucosidase and alpha-amylase, various chalcone-sulfonyl piperazine hybrid compounds (5a-k) were designed and synthesized in this present research. In addition, several spectroscopic methods, including FT-IR, 1 H-NMR, 13 C-NMR, and HRMS, were used to confirm the exact structures of the synthesized derivatives. All synthetic compounds were evaluated for their ability to inhibit alpha-glucosidase and alpha-amylase in vitro using acarbose as the reference standard and they showed excellent to good inhibitory potentials. Compound 5k exhibited excellent inhibitory activity against alpha-glucosidase (IC50 = 0.31 ± 0.01 μM) and alpha-amylase (IC50 = 4.51 ± 1.15 μM), which is 27-fold more active against alpha-glucosidase and 7-fold more active against alpha-amylase compared to acarbose, which had IC50 values of 8.62 ± 1.66 μM for alpha-glucosidase and 30.97 ± 2.91 μM for alpha-amylase.It was discovered from the Lineweaver-Burk plot that 5k exhibited competitive inhibition against alphaglucosidase. Furthermore, cytotoxicity screening assay results against human fibroblast HT1080 cells showed that all compounds had a good level of safety profile. To explore the binding interactions of the most active compound (5k) with the active site of enzymes, molecular docking research was also conducted, and the results obtained supported the experimental data.

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Section: Introductionmentioning

confidence: 99%

Exploring chalcone-sulfonyl piperazine hybrids as anti-diabetes candidates: design, synthesis, biological evaluation, and molecular docking study

Hosseini Nasab,

Raza,

Eom

et al. 2024

Mol Divers

View full text Add to dashboard Cite

show abstract

Section: Introductionmentioning

confidence: 99%

Exploring chalcone-sulfonyl piperazine hybrids as anti-diabetes candidates: Design, synthesis, biological evaluation, and molecular docking study

Nasab,

Raza,

Eom

et al. 2023

Preprint

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To combat the rising rates of diabetes mellitus over the world, novel compounds are required. The demand for more affordable and efficient methods of managing diabetes is increasing due to the unavoidable side effects associated with the existing antidiabetic medications. In order to develop inhibitors against alpha-glucosidase and alpha-amylase, various chalcone-sulfonyl piperazine hybrid compounds (5a–k) were designed and synthesized in this present research. In addition, several spectroscopic methods, including FT-IR, 1H-NMR, 13C-NMR, and HRMS, were used to confirm the exact structures of the synthesized derivatives. All synthetic compounds were evaluated for their ability to inhibit alpha-glucosidase and alpha-amylase in vitro using acarbose as the reference standard and they showed excellent to good inhibitory potentials. Compound 5k exhibited excellent inhibitory activity against alpha-glucosidase (IC50 = 0.31 ± 0.01 µM) and alpha-amylase (IC50 = 4.51 ± 1.15 µM), which is 27-fold more active against alpha-glucosidase and 7-fold more active against alpha-amylase compared to acarbose, which had IC50 values of 8.62 ± 1.66 µM for alpha-glucosidase and 30.97 ± 2.91 µM for alpha-amylase. It was discovered from the Lineweaver-Burk plot that 5k exhibited competitive inhibition against alpha-glucosidase. Furthermore, cytotoxicity screening assay results against human fibroblast HT1080 cells showed that all compounds had a good level of safety profile. To explore the binding interactions of the most active compound (5k) with the active site of enzymes, molecular docking research was also conducted, and the results obtained supported the experimental data.

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Exploring the anti-Alzheimer potential: Design, synthesis, biological activity, and molecular docking study of benzothiazol-1,3,4-oxadiazole-acetamide compounds

Hosseini Nasab,

Raza,

Shim

et al. 2024

Journal of Molecular Structure

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Design, synthesis, and in vitro and in silico studies of 1,3,4-thiadiazole-thiazolidinone hybrids as carbonic anhydrase inhibitors

Abstract: In this study, a series of 1,3,4-thiadiazole-thiazolidinone derivatives (7a–j) were synthesized as carbonic anhydrase inhibitors. The in vitro carbonic anhydrase inhibitory activity of these synthesized compounds was determined and the...

Cited by 5 publications

References 66 publications

Exploring chalcone-sulfonyl piperazine hybrids as anti-diabetes candidates: design, synthesis, biological evaluation, and molecular docking study

Exploring chalcone-sulfonyl piperazine hybrids as anti-diabetes candidates: design, synthesis, biological evaluation, and molecular docking study

Exploring chalcone-sulfonyl piperazine hybrids as anti-diabetes candidates: Design, synthesis, biological evaluation, and molecular docking study

Exploring the anti-Alzheimer potential: Design, synthesis, biological activity, and molecular docking study of benzothiazol-1,3,4-oxadiazole-acetamide compounds

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