Synthesis of benzothiazole derivatives as a potent α-glucosidase inhibitor

Gollapalli, Mohammed; Taha, Muhammad; Javid, Muhammad Tariq; Almandil, Noor B.; Rahim, Fazal; Wadood, Abdul; Mosaddik, Ashik; Ibrahim, Mohamed; Alqahtani, Mohammed A.; Bamarouf, Yasser A.

doi:10.1016/j.bioorg.2018.12.021

Cited by 67 publications

(19 citation statements)

References 34 publications

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“…A docking study was performed to predict the mode of interaction between the identified compounds and the alpha glucosidase enzyme. The homology modelling of S. cerevisiae alpha glucosidase and docking studies have been reported in earlier studies where several compounds were docked with the alpha glucosidase enzyme ( Gollapalli et al., 2019 ; Picot et al., 2017 ; Wang et al., 2017 ). The docking study of the identified compounds are represented in Figure 12 and Figure 13 .…”

Section: Resultsmentioning

confidence: 99%

Alpha glucosidase inhibition activity of phenolic fraction from Simarouba glauca: An in-vitro, in-silico and kinetic study

Mugaranja

Kulal

2020

Heliyon

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A phenolic rich fraction purified from Simarouba glauca leaves was effective in alpha glucosidase inhibition. The purified fraction named ‘fraction-14’ had shown significant inhibition of yeast alpha glucosidase enzyme activity (IC 50 = 2.4 ± 0.4 μg/mL) when compared to anti-diabetic drug acarbose (IC 50 = 2450 ± 24 μg/mL). The purified fraction also had reasonable DPPH (IC 50 = 14.4 ± 0.1 μg/mL) and ABTS (IC 50 = 7.6 ± 0.5 μg/mL) free radical scavenging activity when compared to the standard ascorbic acid. The LC-MS analysis of bioactive ‘fraction-14’ revealed four compounds, eclalbasaponin-v ( 1 ), cyanidin-3-O-(2′galloyl)-galactoside ( 2 ), kaempferol-3-O-glucoside ( 3 ) and kaempferol-3-O-pentoside ( 4 ) for the first time in S. glauca in this study. The kinetic study of the ‘fraction-14’ indicates a mixed type of inhibition on the alpha glucosidase enzyme with K i , 6.2 μg/mL. Docking studies showed promising binding energy for the compounds 2 (-7.769 kJ/mol), 3 (-7.04 kJ/mol) and 4 (-7.127 kJ/mol) against yeast alpha glucosidase which was better than acarbose (-6.867 kJ/mol). In conclusion, the phenolic rich fraction from S. glauca possessing good in-vitro antioxidant property and alpha glucosidase enzyme inhibition potential along with mixed inhibition kinetics. Also, better binding energy of compounds ( 1, 2 & 3 ) appears to contain potential lead-molecule for antidiabetic therapy.

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Section: Resultsmentioning

confidence: 99%

Alpha glucosidase inhibition activity of phenolic fraction from Simarouba glauca: An in-vitro, in-silico and kinetic study

Mugaranja

Kulal

2020

Heliyon

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“…ese five-membered heterocyclic compounds have been proven to possess antibacterial activity and the ability to delocalize free radicals and produce stable DPPH fragments [7]. In addition to antibacterial activity, thiazole derivatives exhibit antimicrobial [8], antiviral [9], antidiabetic [10], anticonvulsant [11], antioxidant [12], anti-HIV [13], antiinflammatory [14], Alzheimer's disease [15], and antitumor activities [16]. Previous studies revealed that 3,5-diaryl-4,5dihydro-1H-pyrazole derivatives, which are members of the 2-pyrazoline class, have been extensively investigated using a variety of structural manipulations and it has been discovered that the steric and electronic properties of the various substituents at the N-1, C-3, and C-5 positions, as well as the chirality aspects of these molecules, have a critical influence on activity [17].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antibacterial, and Antioxidant Activities of Thiazolyl-Pyrazoline Schiff Base Hybrids: A Combined Experimental and Computational Study

Zelelew

Endale

Melaku

et al. 2022

Journal of Chemistry

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Thiazole-pyrazoline Schiff base hybrids have a broad range of pharmacological potential with an ability to control the activity of numerous metabolic enzymes. In this work, a greener and more efficient approach has been developed to synthesize a novel series of thiazole-pyrazoline Schiff base hybrids using ZnO nanoparticle-assisted protocol in good to excellent yields (78.3–96.9%) and examined their antibacterial activity against Gram-positive and Gram-negative bacteria, as well as their antioxidant activity. Compound 24 (IZD = 18.67 ± 0.58) displayed better activity against P. aeruginosa compared with amoxicillin (IZD = 14.33 ± 2.52) at 250 μg/mL, whereas compounds 22 and 24 (IZD = 13.33 ± 0.58 mm and 17.00 ± 1.00 mm, respectively) showed better activity against E. coli compared with amoxicillin (IZD = 14.67 ± 0.58 mm) at 500 μg/mL. The remaining compounds showed moderate to weak activity against the tested bacterial strains. Compound 21 displayed significant inhibition of DPPH (IC50 = 4.63 μg/mL) compared with ascorbic acid (IC50 = 3.21 μg/mL). Compound 21 displayed 80.01 ± 0.07% inhibition of peroxide formation, suggesting its potential in preventing the formation of lipid peroxides. The results of the ADMET study showed that all synthesized compounds obeyed Lipinski's rule of five. In silico pharmacokinetic study demonstrated that compound 24 had superior intestinal absorption compared with amoxicillin. In silico molecular docking analysis revealed a binding affinity of −9.9 Kcal/mol for compound 24 against PqsA compared with amoxicillin (−7.3 Kcal/mol), whereas compounds 22 and 24 displayed higher binding affinity (−8.5 and −7.9 Kcal/mol, respectively) with DNA gyrase B compared with amoxicillin (-7.1 Kcal/mol), in good agreement with in vitro antibacterial activity against P. aeruginosa and E. coli. In silico toxicity study showed that all synthesized compounds had LD50 (mg/kg) values ranging from 800 to 1,000 putting them in ProTox-II class 4. The in vitro antibacterial activity and molecular docking analysis showed that compound 24 is a promising antibacterial therapeutic agent against P. aeruginosa and E. coli and compound 22 is a promising antibacterial agent against E. coli, whereas compound 21 is found to be a potential natural antioxidant agent. Moreover, the green synthesis approach using ZnO nanoparticle as catalyst was found to be a very efficient method to synthesize biologically active thiazole-pyrazoline Schiff base hybrids compared with the conventional method.

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“…α-Glucosidase is an indispensable enzyme in the sugar metabolism pathway of organisms, and its main function is to hydrolyze glycosidic bonds into glucose ( Chaudhry et al, 2019 ; Dan et al, 2019 ; Gollapalli et al, 2019 ; Krishna et al, 2019 ; Mendieta-Moctezuma et al, 2019 ; Spasov et al, 2019 ; Ye et al, 2019 ). Thus inhibiting the α-glucosidase would obviously control the postprandial hyperglycemia.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of 5-Fluoro-2-Oxindole Derivatives as Potential α-Glucosidase Inhibitors

Lin

Liang

et al. 2022

Front. Chem.

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α-Glucosidase inhibitors are known to prevent the digestion of carbohydrates and reduce the impact of carbohydrates on blood glucose. To develop novel α-glucosidase inhibitors, a series of 5-fluoro-2-oxindole derivatives (3a ∼ 3v) were synthesized, and their α-glucosidase inhibitory activities were investigated. Biological assessment results showed that most synthesized compounds presented potential inhibition on α-glucosidase. Among them, compounds 3d, 3f, and 3i exhibited much better inhibitory activity with IC50 values of 49.89 ± 1.16 μM, 35.83 ± 0.98 μM, and 56.87 ± 0.42 μM, respectively, which were about 10 ∼ 15 folds higher than acarbose (IC50 = 569.43 ± 43.72 μM). A kinetic mechanism study revealed that compounds 3d, 3f, and 3i inhibited the α-glucosidase in a reversible and mixed manner. Molecular docking was carried out to simulate the affinity between the compound and α-glucosidase.

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Synthesis of benzothiazole derivatives as a potent α-glucosidase inhibitor

Cited by 67 publications

References 34 publications

Alpha glucosidase inhibition activity of phenolic fraction from Simarouba glauca: An in-vitro, in-silico and kinetic study

Alpha glucosidase inhibition activity of phenolic fraction from Simarouba glauca: An in-vitro, in-silico and kinetic study

Synthesis, Antibacterial, and Antioxidant Activities of Thiazolyl-Pyrazoline Schiff Base Hybrids: A Combined Experimental and Computational Study

Synthesis and Biological Evaluation of 5-Fluoro-2-Oxindole Derivatives as Potential α-Glucosidase Inhibitors

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