Antiglycation and antioxidant potential of novel imidazo[4,5-b]pyridine benzohydrazones

Taha, Muhammad; Al-Kadi, Khaled Abdullah Ali; Ismail, Nor Hadiani; Imran, Syahrul; Adam, Aishah; Kashif, Syed Muhammad; Shah, Syed Adnan Alı; Jamil, Waqas; Sidiqqui, Salman; Khan, Khalid Mohammed

doi:10.1016/j.arabjc.2015.08.004

Cited by 18 publications

(6 citation statements)

References 41 publications

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“…They also reported compound V as an excellent antiglycating agent with IC 50 value of 0.383 ± 0.001 mg/mL as compared to the standard amino guanidine (IC 50 = 0.394 ± 0.001 mg/mL). The nonclassical bioisosterism, antidiabetic properties of halogenated compounds, ,− and in continuation of our research to explore thiazoles in search of an excellent antidiabetic agent guided us in structural planning of the proposed study (Figure ).…”

Section: Introductionmentioning

confidence: 88%

Synthesis of Fluorinated Hydrazinylthiazole Derivatives: A Virtual and Experimental Approach to Diabetes Management

et al. 2023

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A novel series of fluorophenyl-based thiazoles was synthesized following the Hanztsch method. All of the compounds were initially verified with physical parameters (color, melting point, retardation factor (R f)), which were further confirmed by several spectroscopic methods, including ultraviolet–visible (UV–visible), Fourier-transform infrared (FTIR), 1H, 13C, 19F NMR, and high-resolution mass spectrometry (HRMS). The binding interactions of all compounds were studied using a molecular docking simulation approach. Furthermore, each compound was evaluated for its alpha(α)-amylase, antiglycation, and antioxidant potentials. The biocompatibility of all compounds was checked with an in vitro hemolytic assay. All synthesized scaffolds were found biocompatible with minimal lysis of human erythrocytes as compared to the standard Triton X-100. Among the tested compounds, the analogue 3h (IC50 = 5.14 ± 0.03 μM) was found to be a highly potent candidate against α-amylase as compared to the standard (acarbose, IC50 = 5.55 ± 0.06 μM). The compounds 3d, 3f, 3i, and 3k exhibited excellent antiglycation inhibition potential with their IC50 values far less than the standard amino guanidine (IC50 = 0.403 ± 0.001 mg/mL). The antidiabetic potential was further supported by docking studies. Docking studies revealed that all synthesized compounds exhibited various interactions along enzyme active sites (pi–pi, H-bonding, van der Waals) with varied binding energies.

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Section: Introductionmentioning

confidence: 88%

Synthesis of Fluorinated Hydrazinylthiazole Derivatives: A Virtual and Experimental Approach to Diabetes Management

et al. 2023

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“…It is related to high redox potential and the ability to donate electrons. Compound 36 is characterized by the highest antioxidant (EC 50 26.12 µM) and an antiglycation (IC 50 140.16 µM) activity even higher than for references compounds gallic acid and rutin [ 71 , 72 ].…”

Section: Biological Properties Of Imidazo[45- B mentioning

confidence: 99%

Pharmacological Potential and Synthetic Approaches of Imidazo[4,5-b]pyridine and Imidazo[4,5-c]pyridine Derivatives

2017

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The structural resemblance between the fused imidazopyridine heterocyclic ring system and purines has prompted biological investigations to assess their potential therapeutic significance. They are known to play a crucial role in numerous disease conditions. The discovery of their first bioactivity as GABAA receptor positive allosteric modulators divulged their medicinal potential. Proton pump inhibitors, aromatase inhibitors, and NSAIDs were also found in this chemical group. Imidazopyridines have the ability to influence many cellular pathways necessary for the proper functioning of cancerous cells, pathogens, components of the immune system, enzymes involved in carbohydrate metabolism, etc. The collective results of biochemical and biophysical properties foregrounded their medicinal significance in central nervous system, digestive system, cancer, inflammation, etc. In recent years, new preparative methods for the synthesis of imidazopyridines using various catalysts have been described. The present manuscript to the best of our knowledge is the complete compilation on the synthesis and medicinal aspects of imidazo[4,5-b]pyridines and imidazo[4,5-c]pyridines reported from the year 2000 to date, including structure–activity relationships.

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“…Our research group has been evaluating these compounds for their antidiabetic and antioxidant potential since 2015 and reported a variety of pyridines such as dihydropyridines, [ 25 ] pyridine‐3,5‐dicarbonitriles, [ 26 ] imidazo[4,5‐ b ]pyridine benzohydrazone, [ 27 ] aryl thiazole pyridine, [ 28 ] imidazo[4,5‐ b ]pyridines, [ 29 ] dihydropyridine‐3,5‐dicarboxylates, [ 30 ] and pyridine chalcones [ 31 ] as antioxidants as well as α‐amylase and α‐glucosidase enzyme inhibitors (Figure 2). In continuation of our studies on pyridine derivatives, our group has first time synthesized oxy analogs of pyridine which are called pyridones via a one‐pot multicomponent synthesis approach and evaluated them as dual inhibitors of α‐amylase and α‐glucosidase enzymes as well as antioxidants.…”

Section: Introductionmentioning

confidence: 99%

Bioevaluation of synthetic pyridones as dual inhibitors of α‐amylase and α‐glucosidase enzymes and potential antioxidants

Saleem

Khan

Ullah

et al. 2022

Archiv der Pharmazie

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Herein, a library of novel pyridone derivatives 1-34 was designed, synthesized, and evaluated for α-amylase and α-glucosidase inhibitory as well as antioxidant activities. Pyridone derivatives 1-34 were synthesized via a one-pot multicomponent reaction of variously substituted aromatic aldehydes, acetophenone, ethyl cyanoacetate, and ammonium acetate in absolute ethanol. Synthetic compounds 1-34 were structurally characterized by different spectroscopic techniques. Most of the tested compounds showed more promising inhibition potential than the standard acarbose (IC 50 = 14.87 ± 0.16 µM) but compounds 13 and 12 were found to be the most potent compounds with IC 50 values of 9.20 ± 0.14 µM and 3.05 ± 0.18 µM against α-amylase and α-glucosidase enzymes, respectively. Compounds 1-34 also displayed moderate antioxidant potential in the range of IC 50 = 96.50 ± 0.45 to 189.98 ± 1.00 µM in comparison to the control butylated hydroxytoluene (BHT) (IC 50 = 66.50 ± 0.36 µM), in DPPH radical scavenging activities. Additionally, all synthetic derivatives were subjected to a molecular docking study to investigate the interaction details of compounds 1-34 (ligands) with the active site of enzymes (receptors). These results indicate that the newly synthesized pyridone class may serve as promising lead candidates for controlling diabetes mellitus and as antioxidants.

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Antiglycation and antioxidant potential of novel imidazo[4,5-b]pyridine benzohydrazones

Cited by 18 publications

References 41 publications

Synthesis of Fluorinated Hydrazinylthiazole Derivatives: A Virtual and Experimental Approach to Diabetes Management

Synthesis of Fluorinated Hydrazinylthiazole Derivatives: A Virtual and Experimental Approach to Diabetes Management

Pharmacological Potential and Synthetic Approaches of Imidazo[4,5-b]pyridine and Imidazo[4,5-c]pyridine Derivatives

Bioevaluation of synthetic pyridones as dual inhibitors of α‐amylase and α‐glucosidase enzymes and potential antioxidants

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