In vitro α-glucosidase and α-amylase inhibitory potential and molecular docking studies of benzohydrazide based imines and thiazolidine-4-one derivatives

Ullah, Hayat; Uddin, Imad; Khan, Fahad; Sobia,; Taha, Muhammad; Khan, Muhammad Sufaid; Hayat, Shawkat; Ullah, Munzer; Gul, Zarif; Ullah, Shaheed; Zada, Hussan; Javid, Hussain

doi:10.1016/j.molstruc.2021.132058

Cited by 43 publications

(13 citation statements)

References 37 publications

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“…Our research group had identified several heterocyclic compounds as potent therapeutics [28][29][30][31][32][33][34][35][36][37][38][39][40][41][42] and previously published thiazole and sulfonamide derivatives with Sulfonamide-containing compounds have received substantial attention in the last few decades and have emerged as potent inhibitors against various diseases, including diabetes [23], psychosis [24], central nervous system (CNS) disorders [25], tumors [26], and different cancer treatments [27].…”

Section: Introductionmentioning

confidence: 99%

“…Our research group had identified several heterocyclic compounds as potent therapeutics [ 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 ] and previously published thiazole and sulfonamide derivatives with various biological potentials [ 43 , 44 , 45 , 46 ] (see Figure 2 ). Keeping in view the biological importance of thiazole and sulfonamide derivatives, we have planned to design and synthesize a new hybrid class of thiazole-based sulfonamide analogs as acetylcholinesterase and butyrylcholinesterase inhibitors in search of lead candidates.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, DFT Studies, Molecular Docking and Biological Activity Evaluation of Thiazole-Sulfonamide Derivatives as Potent Alzheimer’s Inhibitors

et al. 2023

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Alzheimer’s disease is a major public brain condition that has resulted in many deaths, as revealed by the World Health Organization (WHO). Conventional Alzheimer’s treatments such as chemotherapy, surgery, and radiotherapy are not very effective and are usually associated with several adverse effects. Therefore, it is necessary to find a new therapeutic approach that completely treats Alzheimer’s disease without many side effects. In this research project, we report the synthesis and biological activities of some new thiazole-bearing sulfonamide analogs (1–21) as potent anti-Alzheimer’s agents. Suitable characterization techniques were employed, and the density functional theory (DFT) computational approach, as well as in-silico molecular modeling, has been employed to assess the electronic properties and anti-Alzheimer’s potency of the analogs. All analogs exhibited a varied degree of inhibitory potential, but analog 1 was found to have excellent potency (IC50 = 0.10 ± 0.05µM for AChE) and (IC50 = 0.20 ± 0.050 µM for BuChE) as compared to the reference drug donepezil (IC50 = 2.16 ± 0.12 µM and 4.5 ± 0.11 µM). The structure-activity relationship was established, and it mainly depends upon the nature, position, number, and electron-donating/-withdrawing effects of the substituent/s on the phenyl rings.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, DFT Studies, Molecular Docking and Biological Activity Evaluation of Thiazole-Sulfonamide Derivatives as Potent Alzheimer’s Inhibitors

et al. 2023

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“…The potent nature of the thiazolidinone derivative exhibits versatile behavior with different drug candidates and has a broad spectrum of biological applications including anti-bacterial [ 16 ], anti-fungal [ 17 ], anti-viral [ 18 ], anti-inflammatory [ 19 ], anti-tuberculosis [ 20 ], etc. Benzohydrazide-based imines and 4-thiazolidinone analogs [ 21 ] are used as α-amylase and α-glucosidase inhibitors. The present study also described the basic skeleton and function of thiazolidinone-based benzothiazole derivatives as an effective inhibitor against α-amylase and α-glucosidase enzymes, when compared with the standard drug acarbose.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, In Silico Testing, and In Vitro Evaluation of Thiazolidinone-Based Benzothiazole Derivatives as Inhibitors of α-Amylase and α-Glucosidase

et al. 2022

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In this study, a stepwise reaction afforded thiazolidinone-based benzothiazole derivatives 1–15, and the synthesized derivatives were then screened for biological significance and found to be the leading candidates against α-amylase and α-glucosidase enzymes. Almost all derivatives showed excellent to good activity ranging against α-amylase, IC50 = 2.10 ± 0.70 to 37.50 ± 0.70 μM, and α-glucosidase, IC50 = 3.20 ± 0.05 to 39.40 ± 0.80 μM. Some analogues such as 4 (2.40 ± 0.70 and 3.50 ± 0.70 μM), 5 (2.30 ± 0.05 and 4.80 ± 0.10 μM), and 6 (2.10 ± 0.70 and 3.20 ± 0.70 μM) were found with folds better activity than that of the standard drug acarbose (9.10 ± 0.10 and 10.70 ± 0.10 μM), respectively. Moreover, the structure–activity relationship (SAR) has been established for all compounds. A molecular docking study has been carried out to explore the binding interactions against α-amylase and α-glucosidase enzymes.

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“…For many years, our research group has been working on the design and synthesis of heterocyclic analogues in search of potential lead molecules and has found promising results [ 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ]. We have already reported some benzimidazole analogues as potent α-glucosidase, α-amylase [ 28 ], and α-glucosidase inhibitors [ 29 ] ( Figure 2 ), but there is still a need to discover more derivatives for this inhibitory activity to classify lead candidates for more advanced research in the future.…”

Section: Introductionmentioning

confidence: 99%

Benzimidazole Bearing Thiosemicarbazone Derivatives Act as Potent α-Amylase and α-Glucosidase Inhibitors; Synthesis, Bioactivity Screening and Molecular Docking Study

et al. 2022

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Diabetes mellitus is one of the most chronic metabolic diseases. In the past few years, our research group has synthesized and evaluated libraries of heterocyclic analogs against α-glucosidase and α-amylase enzymes and found encouraging results. The current study comprises the evaluation of benzimidazole-bearing thiosemicarbazone as antidiabetic agents. A library of fifteen derivatives (7–21) was synthesized, characterized via different spectroscopic techniques such as HREI-MS, NMR, and screened against α-glucosidase and α-amylase enzymes. All derivatives exhibited excellent to good biological inhibitory potentials. Derivatives 19 (IC50 = 1.30 ± 0.20 µM and 1.20 ± 0.20 µM) and 20 (IC50 = 1.60 ± 0.20 µM and 1.10 ± 0.01 µM) were found to be the most potent among the series when compared with standard drug acarbose (IC50 = 11.29 ± 0.07 and 11.12 ± 0.15 µM, respectively). These derivatives may potentially serve as the lead candidates for the development of new therapeutic representatives. The structure–activity relationship was carried out for all molecules which are mainly based upon the pattern of substituent/s on phenyl rings. Moreover, in silico docking studies were carried out to investigate the active binding mode of selected derivatives with the target enzymes.

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In vitro α-glucosidase and α-amylase inhibitory potential and molecular docking studies of benzohydrazide based imines and thiazolidine-4-one derivatives

Cited by 43 publications

References 37 publications

Synthesis, DFT Studies, Molecular Docking and Biological Activity Evaluation of Thiazole-Sulfonamide Derivatives as Potent Alzheimer’s Inhibitors

Synthesis, DFT Studies, Molecular Docking and Biological Activity Evaluation of Thiazole-Sulfonamide Derivatives as Potent Alzheimer’s Inhibitors

Design, Synthesis, In Silico Testing, and In Vitro Evaluation of Thiazolidinone-Based Benzothiazole Derivatives as Inhibitors of α-Amylase and α-Glucosidase

Benzimidazole Bearing Thiosemicarbazone Derivatives Act as Potent α-Amylase and α-Glucosidase Inhibitors; Synthesis, Bioactivity Screening and Molecular Docking Study

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