Synthesis, Biological Evaluation, and Molecular Docking of New Benzimidazole-1,2,3-Triazole Hybrids as Antibacterial and Antitumor Agents

Alzahrani, Shareefa Ahmed Saleh; Nazreen, Syed; Elhenawy, Ahmed A.; Neamatallah, Thikryat; Alam, Mohammad Mahbbob

doi:10.1080/10406638.2022.2069133

Cited by 22 publications

(7 citation statements)

References 44 publications

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“…The ligand efficiency was performed for further validation for docking protocol. The ligand efficiency values were within the acceptable range, indicating a reliable docking procedure [51,52] …”

Section: Resultsmentioning

confidence: 70%

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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

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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: Resultsmentioning

confidence: 70%

“…The ligand efficiency values were within the acceptable range, indicating a reliable docking procedure. [51,52]…”

Section: Molecular Docking Analysismentioning

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

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“…Compound 15 a (Figure 21 ) , demonstrated the most promising results with an IC 50 value of 3.23, 6.56, and 5.35 μM against the MCF‐7, HepG2, and HCT‐116 cell lines respectively. The molecular docking study also supported most potent compounds 15 a with interaction similar to erlotinib with EGFR protein [79] …”

Section: Recent Development Of Different Nitrogen Containing Derivati...mentioning

confidence: 62%

“…The molecular docking study also supported most potent compounds 15 a with interaction similar to erlotinib with EGFR protein. [79] A study on the design and synthesis of 1,3,4-triazole compounds as EGFR inhibitors were reported by Kumar et al, in the year 2022. In a cytotoxicity assay, it was discovered that synthetic compounds 16 a and 16 b (Figure 22) were superior to doxorubicin and erlotinib against MCF-7 and HeLa cell lines.…”

Section: Triazolementioning

confidence: 99%

Nitrogen‐Containing Heterocyclic Scaffolds as EGFR Inhibitors: Design Approaches, Molecular Docking, and Structure‐Activity Relationships

Pal¹,

Teli²,

Matada³

et al. 2023

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proved to be the magical weapon in designed and discovery of synthetic molecules as they acquired comprehensive range of pharmacological properties. In recent year (2018-2022) Nheterocyclic derivatives were uncovered as the potential EGFR TKIs. The present review summarised the research progress of EGFR TKIs to dazed the limitations of currently accessible drugs by consecrating, anatomy, mutation of EGFR, and its role in different types of cancer. The review highlights the medicinal chemistry prospective emphasising about the designing strategies, docking studies, biological evaluation, selectivity and structural activity relationship of N-heterocyclic compounds. Our review will support the medicinal chemists in direction for the development of novel N-heterocyclic based EGFR TKIs.

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“…To verify the relationship between the biological findings in vitro and the interaction affinities of the investigated hybrids, the docking analysis of the most active derivatives, 2 , 4 and 6 , was assessed to identify their binding mode inside the (PDB: 1DLS) [ 40 ] and DNA gyrase (PDB; 4uro [ 41 , 42 , 43 ]) active sites, as well as the structural orientation and conformation. The docking steps were applied as in a previously reported method [ 44 , 45 ]. The 3D loop of dihydrofolate-reductase “DHFR” was created using the mGenTHERADER, which utilized the docking framework.…”

Section: Resultsmentioning

confidence: 99%

Exploring Antimicrobial Features for New Imidazo[4,5-b]pyridine Derivatives Based on Experimental and Theoretical Study

et al. 2023

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5-bromopyridine-2,3-diamine reacted with benzaldehyde to afford the corresponding 6-Bromo-2-phenyl-3H-imidazo[4,5-b]pyridine (1). The reaction of the latter compound (1) with a series of halogenated derivatives under conditions of phase transfer catalysis solid–liquid (CTP) allows the isolation of the expected regioisomers compounds (2–8). The alkylation reaction of (1) gives, each time, two regioisomers, N3 and N4; in the case of ethyl bromoactate, the reaction gives, at the same time, the three N1, N3 and N4 regioisomers. The structures of synthesized compounds were elucidated on the basis of different spectral data (1H NMR, 13C NMR), X-Ray diffraction and theoretical study using the DFT method, and confirmed for each compound. Hirshfeld surface analysis was used to determine the intermolecular interactions responsible for the stabilization of the molecule. Density functional theory was used to optimize the compounds, and the HOMO-LUMO energy gap was calculated, which was used to examine the inter/intra molecular charge transfer. The molecular electrostatic potential map was calculated to investigate the reactive sites that were present in the molecule. In order to determine the potential mode of interactions with DHFR active sites, the three N1, N3 and N4 regioisomers were further subjected to molecular docking study. The results confirmed that these analogs adopted numerous important interactions, with the amino acid of the enzyme being targeted. Thus, the most docking efficient molecules, 2 and 4, were tested in vitro for their antibacterial activity against Gram-positive bacteria (Bacillus cereus) and Gram-negative bacteria (Escherichia coli). Gram-positive bacteria were more sensitive to the action of these compounds compared to the Gram-negative, which were much more resistant.

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Synthesis, Biological Evaluation, and Molecular Docking of New Benzimidazole-1,2,3-Triazole Hybrids as Antibacterial and Antitumor Agents

Cited by 22 publications

References 44 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

Nitrogen‐Containing Heterocyclic Scaffolds as EGFR Inhibitors: Design Approaches, Molecular Docking, and Structure‐Activity Relationships

Exploring Antimicrobial Features for New Imidazo[4,5-b]pyridine Derivatives Based on Experimental and Theoretical Study

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