Synthesis, biological evaluation and molecular docking studies of novel benzimidazole derivatives

Singh, Gagandeep; Singh, Amanjot; Verma, Raman K.; Mall, Rajiv; Azeem, Uzma

doi:10.1016/j.compbiolchem.2017.12.010

Cited by 22 publications

(6 citation statements)

References 18 publications

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“…Moreover, some benzimidazole structures having 5-bromo-2-arylbenzimidazole [ 41 ], conjugated biphenylbenzimidazole [ 42 ], benzimidazole linked with morpholine or piperazine [ 43 ], oxadiazole bearing benzimidazole motif [ 44 ], substituted arylbenzimidazol at para-position bridged with thiazolidinone [ 45 ], benzimidazole linked with Schiff base [ 46 ], benzimidazole bearing triazole [ 47 ], hybrid benzimidazole quinolinyl oxadiazole squeleton [ 48 ], hybrid benzimidazole with thiourea [ 49 ], and fluoro-2-substitued-1 H -benzimidazol substituted with morpholine [ 50 ] were reported as α-glucosidase inhibitors. In this context, benzimidazole derived from 5-oxo-pyrido triazepine and aminomethyloxo-pyrimido [ 51 ], benzoylaryl benzimidazole [ 52 ], benzimidazol with substituted benzylidene containing 2,4-thiazolidinedione, diethyl malonate, and methylacetoacetate [ 53 ], and benzimidazole bridged with triazole [ 54 ] also exhibited excellent α-amylase and α-glucosidase activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking, and Bioactivity Study of Novel Hybrid Benzimidazole Urea Derivatives: A Promising α-Amylase and α-Glucosidase Inhibitor Candidate with Antioxidant Activity

et al. 2023

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A novel series of benzimidazole ureas 3a–h were elaborated using 2-(1H-benzoimidazol-2-yl) aniline 1 and the appropriate isocyanates 2a–h. The antioxidant and possible antidiabetic activities of the target benzimidazole-ureas 3a–h were evaluated. Almost all compounds 3a–h displayed strong to moderate antioxidant activities. When tested using the three antioxidant techniques, TAC, FRAP, and MCA, compounds 3b and 3c exhibited marked activity. The most active antioxidant compound in this family was compound 3g, which had excellent activity using four different methods: TAC, FRAP, DPPH-SA, and MCA. In vitro antidiabetic assays against α-amylase and α-glucosidase enzymes revealed that the majority of the compounds tested had good to moderate activity. The most favorable results were obtained with compounds 3c, 3e, and 3g, and analysis revealed that compounds 3c (IC50 = 18.65 ± 0.23 μM), 3e (IC50 = 20.7 ± 0.06 μM), and 3g (IC50 = 22.33 ± 0.12 μM) had good α-amylase inhibitory potential comparable to standard acarbose (IC50 = 14.21 ± 0.06 μM). Furthermore, the inhibitory effect of 3c (IC50 = 17.47 ± 0.03 μM), 3e (IC50 = 21.97 ± 0.19 μM), and 3g (IC50 = 23.01 ± 0.12 μM) on α-glucosidase was also comparable to acarbose (IC50 = 15.41 ± 0.32 μM). According to in silico molecular docking studies, compounds 3a–h had considerable affinity for the active sites of human lysosomal acid α-glucosidase (HLAG) and pancreatic α-amylase (HPA), indicating that the majority of the examined compounds had potential anti-hyperglycemic action.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking, and Bioactivity Study of Novel Hybrid Benzimidazole Urea Derivatives: A Promising α-Amylase and α-Glucosidase Inhibitor Candidate with Antioxidant Activity

et al. 2023

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“…The calculated binding energy values should be minimum for benzimidazole ligands.the calculated binding energy values should be minimum for benzimidazole ligands. The more negative values indicate higher binding affinity [31,32]. The generated ligand values and the compounds showed better scores [33].…”

Section: Discussionmentioning

confidence: 96%

Synthesis, in silico studies and antibacterial activity of some novel 2-substituted benzimidazole derivatives

Chintakunta¹,

Meka²

2020

Futur J Pharm Sci

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Background The o-phenylenediamine is a versatile starting material for several compounds. Synthesized o-phenylenediamine and amino acids (glycine, alanine, aspartic acid, and l-proline) undergo condensation via Phillips reaction. The synthesized compound showed the promising antibacterial activity of Bacillus subtilis and Pseudomonas aeruginosa at the concentration of 100, 50, 25, 12.5, 6.25, 3.12, 1.6, 0.8, 0.4, and 0.2 μg/ml. Ciprofloxacin was used as standard drug. Synthesis of benzimidazole derivatives was carried out and purified by recrystallization process using ethanol. Substituted derivatives were characterized by melting point, TLC and spectroscopic methods include FT-IR and 1H-NMR. Results In silico studies were adopted for synthetic derivatives by Molinspiration, ChemDraw, and online software tool. Minimum inhibitory concentration (MIC) values of B. subtilis and P. aeruginosa were reported, and benzimidazole ligands and Molinspiration scores were generated and listed. Conclusion The more negative values indicate a higher binding affinity. The generated ligand observations can be visualized. Physical constants of synthesized derivates such as solubility and melting point were determined. Bioactivity scores were noted for different derivatives and predicted percentage absorption in the gut. The antibacterial activity was performed using the MIC method (aerobic).

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“…To gain a more meaningful understanding of protein binding of the embarked ligands G1 and G2, we have performed the molecular docking studies by using Surflex-Dock ( Jain, 2003 , 2007 ; Haider et al, 2014 ; Singh et al, 2018 ) application available with SYBYL-X 2.1.1 Software package. The target protein (PPAR-γ bound to PGC-1α; PDB Code: 3CS8) ( Li et al, 2008 ) was sourced from PDB 1 .…”

Section: Methodsmentioning

confidence: 99%

Two Rationally Identified Novel Glitazones Reversed the Behavioral Dysfunctions and Exhibited Neuroprotection Through Ameliorating Brain Cytokines and Oxy-Radicals in ICV-LPS Neuroinflammatory Rat Model

et al. 2020

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The present study has planned to evaluate the neuroprotective activity of two novel glitazones in a neuroinflammatory rat model. Two novel glitazones were selected from an in-house virtual library of glitazones based on their docking scores against peroxisome proliferator-activated receptor-gamma (PPAR-γ) protein and other parameters studied in in silico computational studies. Initially, an acute oral toxicity study was carried out for glitazones in rats to assess the toxicity profile and to determine the therapeutic range for neuroprotective evaluation. Prior to induction of neuroinflammation, the treatments with glitazones (G1 and G2) and standard pioglitazone were made for four consecutive days to respective groups. On the fifth day, the neuroinflammation was induced by intracerebroventricular (ICV) administration of lipopolysaccharides (LPS) (2 µg/µl) using stereotaxic apparatus. After 7 days, the rats were subjected to behavioral assessment followed by neurobiochemical evaluation and histopathological studies. The pretreatment with glitazones at two dose levels (15 and 30 mg/kg) has significantly reversed behavioral dysfunctions. Glitazones have shown significant reduction in the levels of LPO, NO, TNF-α, and IL-1β and also increased the levels of antioxidant enzymes such as SOD, CAT, and GSH in the brain of LPS-administered rats. The neuroprotection exhibited by two novel glitazones is comparable with standard pioglitazone. The PPARγ-dependent amelioration of cytokines and oxy-radicals released by novel glitazones during neuroinflammatory conditions may be attributed to the reversal of behavioral dysfunctions through preventing the degeneration of neurons in major regions of the brain.

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Synthesis, biological evaluation and molecular docking studies of novel benzimidazole derivatives

Cited by 22 publications

References 18 publications

Synthesis, Molecular Docking, and Bioactivity Study of Novel Hybrid Benzimidazole Urea Derivatives: A Promising α-Amylase and α-Glucosidase Inhibitor Candidate with Antioxidant Activity

Synthesis, Molecular Docking, and Bioactivity Study of Novel Hybrid Benzimidazole Urea Derivatives: A Promising α-Amylase and α-Glucosidase Inhibitor Candidate with Antioxidant Activity

Synthesis, in silico studies and antibacterial activity of some novel 2-substituted benzimidazole derivatives

Two Rationally Identified Novel Glitazones Reversed the Behavioral Dysfunctions and Exhibited Neuroprotection Through Ameliorating Brain Cytokines and Oxy-Radicals in ICV-LPS Neuroinflammatory Rat Model

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