Synthesis, molecular structure and urease inhibitory activity of novel bis-Schiff bases of benzyl phenyl ketone: A combined theoretical and experimental approach

Ahmad, Rashid; Khan, Momin; Alam, Aftab; Elhenawy, Ahmed A.; Qadeer, Abdul; Alasmari, Abdullah F.; Alharbi, Metab; Alasmari, Fawaz; Ahmad, Manzoor

doi:10.1016/j.jsps.2023.06.021

Cited by 22 publications

(8 citation statements)

References 37 publications

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“…GOLD was implemented to conduct a docking investigation for the target molecules (version 5.2) alongside its employment in the discovery studio [57] . After attaining the crystallized α‐glucosidase, the H 2 O and inhibitors were removed, and the H atoms were added.…”

Section: Methodsmentioning

confidence: 99%

Investigating Novel Thiophene Carbaldehyde Based Thiazole Derivatives as Potential Hits for Diabetic Management: Synthesis, In Vitro and In Silico Approach

Ullah,

Alam,

Zainab

et al. 2024

ChemistrySelect

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This research work is based on synthesis of eleven novel thiazole derivatives (3 a‐k) of thiophene carbaldehyde. All the synthesized compounds were successfully synthesized, characterized by 1H‐NMR and EI‐MS spectroscopic techniques and finally subjected for their in vitro α‐glucosidase inhibitory activity. Seven derivatives 3 i (IC50=10.21±1.84 μM), 3 b (IC50=11.14±0.99 μM), 3 f (IC50=13.21±2.76 μM), 3 h (IC50=14.21±0.31 μM), 3 k (IC50=15.21±1.02 μM), 3 e (IC50=16.21±1.32 μM), and 3 c (IC50=18.21±1.89 μM), in the series displayed excellent inhibitory potential better than the standard acarbose. However, two compounds 3 g (IC50=33.21±1.99 μM) and 3 d (IC50=42.31±2.12 μM) showed significant activity while two compounds 3 j and 3 a were found less active with IC50 values of 82.31±0.31 and 88.36±1.21 μM respectively. Additional research revealed that the compounds are not exhibiting any cytotoxic effects. The molecular docking study of these derivatives showed their good binding potential for α‐glucosidase active site with excellent interactions and docking scores.

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Section: Methodsmentioning

confidence: 99%

Investigating Novel Thiophene Carbaldehyde Based Thiazole Derivatives as Potential Hits for Diabetic Management: Synthesis, In Vitro and In Silico Approach

Ullah,

Alam,

Zainab

et al. 2024

ChemistrySelect

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“…A number of additional significant variables were calculated using the HOMO→LUMO energy gap (G), including ionization potential (I), electronegativity (E), electron affinity (A), chemical hardness (H), chemical softness (S.), and electrophilicity index ( ώi ). The electrophilicity index is a critical CDFT‐based indicator used to assess bioactivity [44] …”

Section: Resultsmentioning

confidence: 99%

Synthesis of Flurbiprofen Based Amide Derivatives as Potential Leads for Diabetic Management: In Vitro α‐glucosidase Inhibition, Molecular Docking and DFT Simulation Approach

Alam,

Zainab,

Elhenawy

et al. 2024

ChemistrySelect

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This research is based on the synthesis, characterization and in vitro α‐glucosidase inhibitory activity of fourteen amides (2 a–2 n) of flurbiprofen drug. Seven compounds in the series displayed potent inhibitory activity having IC50 values (IC50=5.67±0.89 μM) to (IC50=17.87±2.39 μM) in comparison with acarbose standard (IC50=875.75±1.24 μM). The FMO of 2 a–2 n molecules was quantified by the DFT assay. The promising value for energygap explained the higher poteny agannist α‐glucosidase. MEP provides the insights into the distribution of electrostatic potential on the molecular surface of 2 a–2 n, showing that C=O group has the highest negative potential. The AIM investigation revealed minimal hydrogen bond energy and non‐covalent interactions. This suggests that these molecules may have limited hydrogen bonding and non‐covalent interactions, which could be relevant to their chemical behavior. Molecular docking and (MEP) showed the C=O group, with its high negative potential, is a key in recognizing the catalytic non‐polar regions of enzymes, such as TYR72, GLU277, and ARG442. Similarly, the hydrophobic regions of investigated compounds play a significant role in identifying essential amino acids like ASP352 and ARG442, which are vital for the ligand's proper orientation and subsequent biological activity.

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“…A variety of transition metal complexes (TMCs) serving as UIs have been identified in recent years. − Cu-based TMCs show stronger urease inhibitory efficacy than other metal-based TMCs . Meanwhile, coordination polymers (CPs) are a class of hybrid materials composed of organic linkers and bridging metal ions or clusters. − They have variable pore size, a high specific surface area, and strong biocompatibility. − The CP contains both metal and organic ligands and exhibits excellent water stability, making it suitable as a UI .…”

Section: Introductionmentioning

confidence: 99%

Fabrication of Substituent-Regulated Two-Dimensional Copper-Based Coordination Polymers as Urease Inhibitors

Duan,

Li,

Yan

et al. 2024

Crystal Growth & Design

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This article reports the design and synthesis of two copper-based coordination polymers (Cu-CPs) constructed from mixed ligands containing a bis-pyridine-bis-amide group and trimellitic acid. By using substituent-regulated acids, the simplified two-dimensional (2D) double layers for the Cu-CP-1 and Cu-CP-2 possess different grid windows, which can be served as a kind of urease inhibitors (UIs) and their inhibition mechanisms were explored in details. The results show that both Cu-CPs exhibited good urease inhibitory activity, and the inhibitory activities of all derivatives were higher than that of the standard thio urea, with UI-2 exhibiting better urease inhibitory performance. To better understand the potential mechanism of urease inhibition by these CPs, enzyme kinetics analysis was performed using Lineweaver− Burk (L−B) plots at different inhibitor concentrations, which indicated that UI-1 and UI-2 exhibited noncompetitive inhibitory nature. Additionally, molecular docking confirmed the binding interactions of UI-1 and UI-2 with the active site of urease. The urease inhibition experiments were successfully verified, and the effects of the structures of CPs on urease inhibition were measured through DFT calculations.

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Synthesis, molecular structure and urease inhibitory activity of novel bis-Schiff bases of benzyl phenyl ketone: A combined theoretical and experimental approach

Cited by 22 publications

References 37 publications

Investigating Novel Thiophene Carbaldehyde Based Thiazole Derivatives as Potential Hits for Diabetic Management: Synthesis, In Vitro and In Silico Approach

Investigating Novel Thiophene Carbaldehyde Based Thiazole Derivatives as Potential Hits for Diabetic Management: Synthesis, In Vitro and In Silico Approach

Synthesis of Flurbiprofen Based Amide Derivatives as Potential Leads for Diabetic Management: In Vitro α‐glucosidase Inhibition, Molecular Docking and DFT Simulation Approach

Fabrication of Substituent-Regulated Two-Dimensional Copper-Based Coordination Polymers as Urease Inhibitors

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