Synthesis, structural characterization and antibacterial activity evaluation of novel quinolone-1,2,3-triazole-benzimidazole hybrids

Gadali, Khadija El; Rafya, Meriem; Mansouri, Az-Eddine El; Maatallah, Mohamed; Lee, Arie van der; Mehdi, Ahmad; Ouahrouch, Abdelaaziz; Benkhalti, Fatiha; Sanghvi, Yogesh S.; Taourirte, Moha; Lazrek, H. B.

doi:10.1016/j.molstruc.2023.135179

Cited by 9 publications

(2 citation statements)

References 59 publications

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“…According to the results obtained from MTT, it is evident that these two compounds are effective in inhibiting the growth of colon cancerous cells. In particular, it was found that the compound containing the anthracene group, which name is 1-(anthracen-10-ylmethyl)-1H-benzo[d]imidazole (3), showed a much higher antiproliferative effect compared to the compound, 1-(2,3,5,6-tetramethylbenzyl)-1H-benzo[d]imidazole (2), containing the tetramethyl group with an IC 50 value of 46.91 μM in DLD-1. As a result, it was demonstrated that both molecules exhibited lower cytotoxic activities against DLD-1 than cisplatin with an IC 50 value of 23.31 μM.…”

Section: Cytotoxic Activitymentioning

confidence: 99%

“…Organic compounds bearing benzimidazole nuclei are known to be important fragments in medicinal chemistry due to their broad biological activities. In studies conducted by researchers, it was found that compounds containing benzimidazole core (mono‐, bis‐, and tris‐benzimidazoles) showed antiproliferative, [1] antibacterial, [2] antifungal, [3] antiviral, [4] anti‐oxidant, [5] antidepressant, [6] anti‐tubercular, [7] anti‐inflammatory, [8] anti‐hypertension, [9] and anti‐ulcerative [10] activities. It is also reported in the literature that benzimidazole‐based molecules have cardioprotective properties [11] …”

Section: Introductionmentioning

confidence: 99%

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In Vitro and In Silico Studies on Benzimidazole‐Based Compounds

Bouchekioua,

Akkoc,

Menacer

2024

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Colon cancer remains a significant health concern, necessitating the synthesis of novel therapeutic agents. Benzimidazole derivatives have shown promising anticancer potential. In this study, two benzimidazole derivatives were synthesized, and their antiproliferative activities were investigated in vitro against the human colon colorectal cancer cell line and the human normal lung fibroblast cell line. The cell viability revealed that molecule 3 had high antiproliferative activity and inhibited the growth of DLD‐1 cells for 48 h. Furthermore, molecule 3 was found to have more selectivity against the human normal cell line. Computational calculations were performed to predict the molecular properties of molecules using the B3LYP/6‐311++(2d,2p) density functional theory level. The quantum theory of atoms in molecules (QTAIM) and energy decomposition analysis (EDA) were utilized to investigate the nature of the interatomic bonding existing among the studied molecules. The ultraviolet‐visible (UV–vis) results for molecules were calculated using time‐dependent density‐functional theory (TD‐DFT). The chemical reactivity and molecular stability were also investigated by DFT computational analysis. The molecular docking and dynamics simulations were conducted, and their results reveal their concordance with the experimental results. Molecule 3 has better anti‐cancer activity against colon cancer targets (PDB ID: 2HQ6) compared to molecule 2.

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Section: Cytotoxic Activitymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

In Vitro and In Silico Studies on Benzimidazole‐Based Compounds

Bouchekioua,

Akkoc,

Menacer

2024

ChemistrySelect

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Fused Imidazo[1,2‐d][1,2,4]Thiadiazolo[1,2,3]Triazoles: One‐Pot Synthesis, Anti‐Bacterial, Anti‐Biofilm and TLR4 Inhibitory Activities

Premalatha,

Azam,

Kapavarapu

et al. 2024

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We developed and evaluated several new fused imidazo[1,2‐d][1,2,4]thiadiazolo[1,2,3]triazoles to see how they perform against bacteria and biofilms. Some compounds showed acceptable activity compared to the primary standard, Dicloxacillin. Some of the compounds demonstrated significant antibacterial activity against S. aureus, with MIC values ranging from 1.56–12.5 μg/mL. We also found anti‐biofilm properties in the potent compounds. The results showed that derivatives 3‐(4‐fluorophenyl)imidazo[1,2‐d] [1,2,3] triazolo[1,5‐b][1,2,4]thiadiazole 8,8‐dioxide and 3‐(3,5‐difluorophenyl)imidazo[1,2‐d][1,2,3]triazolo[1,5‐b][1,2,4] thiadiazole 8,8‐dioxide were strong antibacterial agents and effective MSSA and MRSA biofilm growth inhibitors. We conducted in silico studies to assess the molecular interactions of more potent compounds with TLR4 proteins (PDB: 3FXI, 3VQ1, 3RG1). Our findings revealed that 3‐(4‐chloro‐3,5‐dimethoxyphenyl)imidazo[1,2‐d][1,2,3]triazolo[1,5‐b] [1,2,4]thiadiazole 8,8‐dioxide, 3‐(3,5‐dichlorophenyl)imidazo[1,2‐d] [1,2,3]triazolo[1,5‐b][1,2,4] thiadiazole 8,8‐dioxide, and 3‐(4‐(trifluoromethyl)phenyl)imidazo[1,2‐d][1,2,3]triazolo[1,5‐b][1,2,4] thiadiazole 8,8‐dioxide exhibited more binding interactions than dicloxacillin. ADME of more potent compounds examined in this study and compounds could potentially inhibit the cytochrome P450 CYP2C19 isoform.

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