Synthesis of ethyl 6‐aryl‐4‐oxo‐4,6‐dihydro‐1(12)(13)<i>h</i>‐pyrimido‐[2′,1′:4,5][1,3,5]triazino[1,2‐<i>a</i>]benzimidazole‐3‐carboxylates

Dolzhenko, Anton V.; Chui, Wai Keung; Dolzhenko, Anna V.

doi:10.1002/jhet.5570430614

Cited by 19 publications

(4 citation statements)

References 16 publications

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“…In particular tricyclic benzimidazole derivatives have been investigated as potential inhibitors of dihydrofolate reductase in the search for anticancer and antibacterial agents [29][30][31] and for DNA intercalating agents [31].…”

Section: Introductionmentioning

confidence: 99%

Triphenyl lead, tin and germanium coordination compounds derived from 9H-3-thia-1,4a,9-triaza-fluorene-2,4-dithione

Peña-Hueso

Esparza‐Ruiz

Ramos-Garcı́a

et al. 2008

Journal of Organometallic Chemistry

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Section: Introductionmentioning

confidence: 99%

Triphenyl lead, tin and germanium coordination compounds derived from 9H-3-thia-1,4a,9-triaza-fluorene-2,4-dithione

Peña-Hueso

Esparza‐Ruiz

Ramos-Garcı́a

et al. 2008

Journal of Organometallic Chemistry

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“…The target hybrids 3–11 were synthesized in good yields via nucleophilic aromatic substitution of fluoride − of the starting material 2,4-dinitrofluorobenzene with various N , S , and O nucleophiles 1a–i , namely, (3-(3-oxo-3,4-dihydroquinoxalin-2-yl)-1-phenyl-1 H -pyrazol-5-yl)methylacetate ( 1a ), 3-methylquinoxalin-2(1 H )-one ( 1b ), 3-benzylquinoxalin-2(1 H )-one ( 1c ), benzo[ d ]thiazole-2-thiol ( 1d ), 1-methyl-2-thiouracil ( 1e ), 8-hydroxyquinoline ( 1f ), 2,6-di- tert -butylphenol ( 1g ), piperazine ( 1h ), and imidazole ( 1i ), under reflux in acetone as an aprotic solvent in the presence of anhydrous K 2 CO 3 to enhance nucleophilic aromatic substitutions, as shown in Scheme . The structures of 2,4-dinitrophenyl derivatives 3–11 were established based on their spectral data.…”

Section: Resultsmentioning

confidence: 99%

Exploration of Nitroaromatic Antibiotics via Sanger’s Reagent: Synthesis, In Silico, and Antimicrobial Evaluation

et al. 2022

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Facile synthesis of molecular hybrids containing a 2,4-dinitrophenyl moiety was achieved via nucleophilic aromatic substitution of the fluoride anion of Sanger’s reagent (2,4-dinitrofluorobenzene) with various N, S, and O nucleophiles, considered as bioactive moieties. Antimicrobial evaluation of the new hybrids was carried out using amoxicillin and nystatin as antibacterial and antifungal reference standards, respectively. MIC test results identified the compounds 3, 4, and 7 as the most active hybrids against standard strains and multidrug-resistant strains (MDR) of Staphylococcus aureus, Escherichia coli, and Pseudomonas aurginosa. Most of the hybrids displayed two times the antibacterial activity of AMOX against MDR Pseudomonas aeruginosa, E. coli, and a standard strain of P. aeruginosa (ATCC 29853), while demonstrating a weak antifungal profile against Candida albicans. Selectivity profiles of the promising compounds 3, 4, 6, 7, 8, and 11 on WI-38 human cells were characterized, which indicated that compound 3 is the safest one (CC50 343.72 μM). The preferential anti-Gram-negative activity of our compounds led us to do docking studies on DNA gyrase B. Docking revealed that the potential antimicrobial compounds fit well into the active site of DNA gyrase B. Furthermore, in silico absorption, distribution, metabolism, and excretion (ADME) predictions revealed that most of the new compounds have high gastrointestinal absorption and a good oral bioavailability with no BBB permeability.

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“…On the other hand, triazines are another class of heterocyclic compounds that have demonstrated significant potential as antiparasitic agents; more especially, the 1,3,5-triazine derivatives have shown excellent anti-malarial activity [ 11 , 12 , 13 ]. Agarwal et al conducted a study where they synthesized a series of 2,4,6-trisubstituted-1,3,5-triazines ( Figure 1 ) and evaluated their in vitro antimalarial activity against P. falciparum .…”

Section: Introductionmentioning

confidence: 99%

Fused Triazinobenzimidazoles Bearing Heterocyclic Moiety: Synthesis, Structure Investigations, and In Silico and In Vitro Biological Activity

et al. 2023

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[1,3,5]Triazino[1,2-a]benzimidazole-2-amines bearing heterocyclic moiety in 4-position were synthesized. The compounds were characterized by elemental analysis, IR, 1H-NMR, 13C-NMR, and HRMS spectroscopy. The molecular geometry and electron structure of these molecules were theoretically studied using density functional theory (DFT) methods. The molecular structure of the synthesized fused triazinobenzimidazole was confirmed to correspond to the 3,4-dihydrotriazinobenzimidazole structure through the analysis of spectroscopic NMR data and DFT calculations. The antinematodic activity was evaluated in vitro on isolated encapsulated muscle larvae (ML) of Trichinella spiralis. The results showed that the tested triazinobenzimidazoles exhibit significantly higher efficiency than the conventional drug used to treat trichinosis, albendazole, at a concentration of 50 μg/mL. The compound 3c substituted with a thiophen-2-yl moiety exhibited the highest anthelmintic activity, with a larvicidal effect of 58.41% at a concentration of 50 μg/mL after 24 h of incubation. Following closely behind, the pyrrole analog 3f demonstrated 49.90% effectiveness at the same concentration. The preliminary structure-anti-T. spiralis activity relationship (SAR) of the analogues in the series was discussed. The cytotoxicity of the benzimidazole derivatives against two normal fibroblast cells (3T3 and CCL-1) and two cancer human cell lines (MCF-7 breast cancer cells and chronic myeloid leukemia cells AR-230) was evaluated using the MTT-dye reduction assay. The screening results indicated that the compounds showed no cytotoxicity against the tested cell lines. An in silico study of the physicochemical and pharmacokinetic characteristics of the novel synthesized fused triazinobenzimidazoles showed that they were characterized by a significant degree of drug-likeness and optimal properties for anthelmintic agents.

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Synthesis of ethyl 6‐aryl‐4‐oxo‐4,6‐dihydro‐1(12)(13)h‐pyrimido‐[2′,1′:4,5][1,3,5]triazino[1,2‐a]benzimidazole‐3‐carboxylates

Cited by 19 publications

References 16 publications

Triphenyl lead, tin and germanium coordination compounds derived from 9H-3-thia-1,4a,9-triaza-fluorene-2,4-dithione

Triphenyl lead, tin and germanium coordination compounds derived from 9H-3-thia-1,4a,9-triaza-fluorene-2,4-dithione

Exploration of Nitroaromatic Antibiotics via Sanger’s Reagent: Synthesis, In Silico, and Antimicrobial Evaluation

Fused Triazinobenzimidazoles Bearing Heterocyclic Moiety: Synthesis, Structure Investigations, and In Silico and In Vitro Biological Activity

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