Synthesis, bioactivity, and molecular docking of benzimidazole-2-carbamate derivatives as potent α-glucosidase inhibitors

Moghadam, Ebrahim Saeedian; Al-Sadi, Abdullah M.; Al-Harthy, Thuraya; Faramarzi, Mohammad Ali; Shongwe, Musa S.; Amini, Mohsen; Abdel‐Jalil, Raid J.

doi:10.1016/j.molstruc.2023.134931

Cited by 5 publications

(3 citation statements)

References 29 publications

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“…The enzyme solution (1 U/mL, 20 μ L) was incubated with different concentrations of the most active compound 5 g (20 μL) for 15 min at 30 °C. Different concentrations of pNPG (1–10 mM) was added as a substrate to initiate the reaction in the absence and presence of compound 7 e and change in the absorbance was determined for 20 min at 405 nm by using spectrophotometer (Gen5, Power wave xs2, BioTek, America) [46–48] . A Lineweaver–Burk plot was generated to identify the type of inhibition and the Michaelis–Menten constant ( K m ) value was determined from plot between reciprocal of the substrate concentration (1/[S]) and reciprocal of enzyme rate (1/ V ) over various inhibitor concentrations.…”

Section: Methodsmentioning

confidence: 99%

“…Different concentrations of pNPG (1-10 mM) was added as a substrate to initiate the reaction in the absence and presence of compound 7 e and change in the absorbance was determined for 20 min at 405 nm by using spectrophotometer (Gen5, Power wave xs2, BioTek, America). [46][47][48] A Lineweaver-Burk plot was generated to identify the type of inhibition and the Michaelis-Menten constant (K m ) value was determined from plot between reciprocal of the substrate concentration (1/[S]) and reciprocal of enzyme rate (1/V) over various inhibitor concentrations. Experimental inhibitor constant (K i ) value was constructed by secondary plots of the inhibitor concentration [I] versus K m .…”

Section: Enzyme Kinetic Studymentioning

confidence: 99%

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Preparation of Novel 3,4,5‐Triaryl‐1,2,4‐Oxadiazole Derivatives: Molecular Docking and α‐Glucosidase assessment

Roustaei,

Saeedian Moghadam,

Faramarzi

et al. 2024

ChemistrySelect

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Diabetes mellitus (DM) has become a growing health problem, across all globe. Many factors have contributed into this issue, among them inappropriate lifestyle, unhealthy eating habits and growing spiritual/mental concerns are to be rated higher. Likewise much research needed to be diverted in progress for treatment of DM. Herein, we report synthesis and antidiabetic activity evaluation of ten novel phenolic derivatives of triaryl‐1,2,4‐oxadiazole 7 a–j. The compounds have synthesized using multistep reactions in acceptable purity and yields. Final step was done using 1,3‐dipolar cycloaddition reaction between various Schiff bases and arylnitrile oxides. 7 a–j were characterized by spectroscopic methods (1H NMR, 13C NMR, MS and IR) and their purities were confirmed using elemental analysis. All 7 a–j were evaluated for their α‐Glucosidase inhibitory activity. All compounds showed higher activity in inhibiting the enzyme, in comparison to standard, acarbose. Compounds 7 e and 7 g exerted the best activity with the IC50 value of 193.6 and 222.0 μM respectively. Furthermore, enzyme kinetic study approach was adopted to judge the effect of 7 e on enzyme inhibition. Finally, docking simulations revealed the possible mode of interactions between 7 e and 7 g and enzyme active sites. Final conclusion of results showed that oxadiazole scaffold/s are a potential antidiabetic target.

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Section: Methodsmentioning

confidence: 99%

Section: Enzyme Kinetic Studymentioning

confidence: 99%

Preparation of Novel 3,4,5‐Triaryl‐1,2,4‐Oxadiazole Derivatives: Molecular Docking and α‐Glucosidase assessment

Roustaei,

Saeedian Moghadam,

Faramarzi

et al. 2024

ChemistrySelect

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“…The yellow-orange solid was precipitated out which was filtered off and recrystallized from ethanol to get pure compound 4. [23] 5-Chloro-4-fluoro-2-nitrobenzenamine 4 (1 mmol) was added to DMSO (15 mL) in a suitable glass flask, followed by addition of Nmethyl piperazine (2.5 mmol). After the addition completed, the mixture was refluxed for 2 hours.…”

Section: Experimental Chemistrymentioning

confidence: 99%

New Bioactive Dipiperazine Derivatives; Synthesis, Molecular Docking and Urease Inhibition Study

et al. 2023

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The successful colonization and survival of highly pathogenic bacteria are powerfully aided by an enzyme known as urease. As a result, it has been demonstrated that inhibiting urease enzymes is a promising method for preventing ureolytic bacterial infections. Consequently, the development and synthesis of safe and effective urease inhibitors has emerged as an intriguing field of study for medical chemists. In this paper, synthesis and bioactivity of thirteen novel benzimidazole derivatives are reported as strong urease inhibitors. The structure of target compounds was determined through a variety of spectroscopic methods (HRMS, 1H NMR, IR). Intriguingly, the inhibitory activity of all was higher (IC50: 9.49 to 23.50 μM) than hydroxyurea, which represent the standard (IC50: 100 μM). In conclusion, current compounds that have been reported are potent enough to continue bioassays to discover a new drug candidate.

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Thiazolidine-2,4-dione derivatives as potential α-glucosidase inhibitors: Synthesis, inhibitory activity, binding interaction and hypoglycemic activity

Li,

Sun,

Liang

et al. 2024

Bioorganic Chemistry

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Synthesis, bioactivity, and molecular docking of benzimidazole-2-carbamate derivatives as potent α-glucosidase inhibitors

Cited by 5 publications

References 29 publications

Preparation of Novel 3,4,5‐Triaryl‐1,2,4‐Oxadiazole Derivatives: Molecular Docking and α‐Glucosidase assessment

Preparation of Novel 3,4,5‐Triaryl‐1,2,4‐Oxadiazole Derivatives: Molecular Docking and α‐Glucosidase assessment

New Bioactive Dipiperazine Derivatives; Synthesis, Molecular Docking and Urease Inhibition Study

Thiazolidine-2,4-dione derivatives as potential α-glucosidase inhibitors: Synthesis, inhibitory activity, binding interaction and hypoglycemic activity

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