Synthesis, in vitro α-glucosidase inhibitory activity and molecular docking studies of new thiazole derivatives

Khan, Khalid Mohammed; Qurban, Saira; Salar, Uzma; Taha, Muhammad; Hussain, Shafqat; Perveen, Shahnaz; Hameed, Abdul; Ismail, Nor Hadiani; Riaz, Muhammad; Wadood, Abdul

doi:10.1016/j.bioorg.2016.08.010

Cited by 43 publications

(16 citation statements)

References 26 publications

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“…45 analogues of the studied compounds and their αglucosidase inhibitory activities (IC50) were downloaded from the work of (Rahim et al, 2015) and (Khan et al, 2016) for the purpose of this research. The inhibitory activities (IC50) (μM) of the dataset were converted to pIC50 (Ibrahim et al, 2018a).…”

Section: Sources Of the Datasetmentioning

confidence: 99%

“…Thiazole and its derivatives have wide industrial application in pharmacy, liquid crystals, and polymers (de Souza, 2005). Thiazoles have several biological activities such as antioxidant, insecticidal, antitumor, anticonvulsant, anti-hyperlipidemic and antiinflammatory (Khan et al, 2016) Computer-aided drug design (CADD) is a unique area in drug discovery arena which apply the concept of molecular modelling to study the interaction between drugs and their target protein (Bibi and Sakata, 2016). QSAR is a molecular modeling technique widely used to correlate physicochemical properties of compounds and their experimentally determined activities (Alisi et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

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QSAR modelling and docking analysis of some thiazole analogues as alfa-glucosidase inhibitors

2019

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QSAR modelling and docking studies on 45 thiazole analogues were carried out. The studied compounds in this research were optimized adopting DFT method at B3LYP function with a 6-31G* basis set. The QSAR models were generated in material studio by MLR analysis (GFA method). Based on its statistical fitness, the first model was selected and reported as the best model and assessed with R 2 = 0.906134, R 2 adj = 0.89049, Q 2 cv = 0.86149 and R 2 pred = 0.82581 statistical parameters. The ligand with the highest binding energy of-11.0 kcal/mol among the other ligands was ligand 13 as indicated by the molecular docking. The standard drug (acarbose) was also docked to the binding pocket of ⍺-glucosidase with-9.5kcal/mole docking score. The most active compound was found to be better than standard drug. The outcome of this findings paved way for predicting novel ⍺-glucosidase inhibitors having improved potency toward their target enzyme.

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Section: Sources Of the Datasetmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

QSAR modelling and docking analysis of some thiazole analogues as alfa-glucosidase inhibitors

2019

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“…A Schiff base unit is a valuable pharmacophore that has been found in numerous biologically active compounds such as analgesic, antioxidant, antileishmanial, and antidiabetic agents . Recently, several series of α‐glucosidase inhibitors containing Schiff bases such as compounds A , B , and C have been reported (Figure ) . In contrast, 1,2,3‐triazoles are an important class of heterocycles, which have a wide spectrum of pharmaceutical applications.…”

Section: Introductionmentioning

confidence: 99%

A new series of Schiff base derivatives bearing 1,2,3‐triazole: Design, synthesis, molecular docking, and α‐glucosidase inhibition

Nasli‐Esfahani

Mohammadi‐Khanaposhtani

Rezaei

et al. 2019

Archiv der Pharmazie

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A series of new Schiff bases bearing 1,2,3‐triazole 12a‒o was designed, synthesized, and evaluated as α‐glucosidase inhibitors. All the synthesized compounds showed promising inhibition against α‐glucosidase and were more potent than the standard drug acarbose. The kinetic study on the most potent compound 12n showed that this compound acted as a competitive α‐glucosidase inhibitor. The docking study revealed that the synthesized compounds interacted with the important residues in the active site of α‐glucosidase.

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“…Thiazoles are five‐membered heterocyclic compounds bearing sulfur and nitrogen in the ring and plays an essential role in medicinal and pharmaceutical chemistry. Thiazoles are endowed with potential biological activities such as anticancer, antitubercular, α ‐glucosidase inhibitor, antioxidant, antibacterial, antiplatelet, anti‐inflammatory, anti‐Candida activity, and antifungal properties . In addition, thiamine or vitamin B 1 is one of the most important natural thiazoles.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antimicrobial, and antioxidant activities of new pyridyl‐ and thiazolyl‐bearing carbohydrazides

Muluk

Phatak

Pawar

et al. 2019

J Chinese Chemical Soc

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A series of novel substituted (E)‐N′‐benzylidene‐4‐methyl‐2‐(2‐propylpyridin‐4‐yl)thiazole‐5‐carbohydrazide derivatives (6a‐l) have been synthesized by following the multistep synthetic route starting from prothionamide. The resulting compounds were characterized via 1H, 13C NMR, and HRMS spectral data. The synthesized carbohydrazides were evaluated for their in vitro antimicrobial and antioxidant activities. Tested molecules have displayed moderate to good growth inhibition activity. Among the screened compounds, 6b, 6e, 6j, and 6k are found to be the more promising antimicrobial agents. A 2,2‐diphenyl‐1‐picrylhydrazyl assay was used to test the antioxidant activity of the carbohydrazides. The carbohydrazide derivatives 6b and 6i have shown better free‐radical scavenging ability than the other investigated compounds.

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Synthesis, in vitro α-glucosidase inhibitory activity and molecular docking studies of new thiazole derivatives

Cited by 43 publications

References 26 publications

QSAR modelling and docking analysis of some thiazole analogues as alfa-glucosidase inhibitors

QSAR modelling and docking analysis of some thiazole analogues as alfa-glucosidase inhibitors

A new series of Schiff base derivatives bearing 1,2,3‐triazole: Design, synthesis, molecular docking, and α‐glucosidase inhibition

Synthesis, antimicrobial, and antioxidant activities of new pyridyl‐ and thiazolyl‐bearing carbohydrazides

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