A unique one-pot reaction via CC cleavage from aminomethylene benzimidazoles to access benzimidazolones with wide potentiality

Zhang, Huizhen; Cui, Sheng‐Feng; Nagarajan, Sangaraiah; Syed, Rabbani; Cai, Gui‐Xin; Zhou, Cheng‐He

doi:10.1016/j.tetlet.2014.05.113

Cited by 17 publications

(7 citation statements)

References 28 publications

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“…Particularly,a ltera-tions in the conserved ParC helix a4 residues of the topoisomerase IV-DNA complex, positioned in close proximity to the groups at the N1 positiono fq uinolones, directly weakened the binding affinity between quinolonea ntimicrobials and target enzymes. [17][18][19] Benzimidazole derivatives couldi nteract with DNA from different microbial strains or inhibitt he biosynthesis of essential ergosterol in the membrane of fungi and protozoa to exhibit antimicrobial activity. [14][15][16] Benzimidazole, with al arge, conjugated, rigid, planar structure, is structurallys imilart op urine nucleoside bases,a nd has been attracting increasing interest in drug design for the development of potentiala ntimicrobiala gents.…”

Section: Introductionmentioning

confidence: 99%

“…[14][15][16] Benzimidazole, with al arge, conjugated, rigid, planar structure, is structurallys imilart op urine nucleoside bases,a nd has been attracting increasing interest in drug design for the development of potentiala ntimicrobiala gents. [17][18][19] Benzimidazole derivatives couldi nteract with DNA from different microbial strains or inhibitt he biosynthesis of essential ergosterol in the membrane of fungi and protozoa to exhibit antimicrobial activity. [20,21] Previous studies reported that some benzimidazole-based hybrids, such as sulfonamides, 5-fluorouracils, and naphthalimides, exhibitedg ood antimicrobiala ctivities and a broad antibacterial spectrum.…”

Section: Introductionmentioning

confidence: 99%

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Discovery of Benzimidazole–Quinolone Hybrids as New Cleaving Agents toward Drug‐Resistant Pseudomonas aeruginosa DNA

et al. 2018

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A series of benzimidazole-quinolone hybrids as new potential antimicrobial agents were designed and synthesized. Bioactive assays indicated that some of the prepared compounds exhibited potent antibacterial and antifungal activities. Notably, 2-fluorobenzyl derivative 5 b (ethyl 7-chloro-6-fluoro-1-[[1-[(2-fluorophenyl)methyl]benzimidazol-2-yl]methyl]-4-oxo-quinoline-3-carboxylate) showed remarkable antimicrobial activity against resistant Pseudomonas aeruginosa and Candida tropicalis isolated from infected patients. Active molecule 5 b could not only rapidly kill the tested strains, but also exhibit low toxicity toward Hep-2 cells. It was more difficult to trigger the development of bacterial resistance of P. aeruginosa against 5 b than that against norfloxacin. Molecular docking demonstrated that 5 b could effectively bind with topoisomerase IV-DNA complexes, and quantum chemical studies theoretically elucidated the good antimicrobial activity of compound 5 b. Preliminary experimental reaction mechanism exploration suggested that derivative 5 b could not intercalate into DNA isolated from drug-resistant P. aeruginosa, but was able to cleave DNA effectively, which might further block DNA replication to exert powerful bioactivities. In addition, compound 5 b is a promising antibacterial agent with membrane disruption abilities.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Discovery of Benzimidazole–Quinolone Hybrids as New Cleaving Agents toward Drug‐Resistant Pseudomonas aeruginosa DNA

et al. 2018

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“…Based on this, a novel type of quinolone imidazoles was designed. Benzimidazole is a fused ring of imidazole with benzene having larger conjugated system and electron richer properties than imidazole, and this unique structure endows its derivatives to possess extensive potentiality in medicinal chemistry especially antimicrobial aspect . Herein, we also would like to develop this fused ring type of nitroimidazole derivatives including 2‐methyl‐5‐nitrobenzimidazole, 6‐nitrobenzimidazole, 2‐methylbenzimidazole, 5,6‐dimethylbenzimidazole, benzimidazole, and 2‐thiol‐benzimidazole as wholly new structure type of antimicrobial agents to investigate the effect of azole moiety on biological activities which were expected to have large roles in the treatment of disease‐causing bacteria and fungi.…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, and Antimicrobial Evaluation of Novel Quinolone Imidazoles and Interactions with MRSA DNA

et al. 2015

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A novel series of quinolone imidazoles as new type of antimicrobial agents were synthesized. Most compounds exhibited good bioactivities especially against MRSA even superior to reference drugs. They induced bacterial resistance more slowly than clinical drugs and gave low cytotoxicity to human cells. The pKa values of these compounds showed appropriate ranges to pharmacokinetic behaviors. The interactions between compound 8b, Cu(2+) ion, and MRSA DNA revealed that compound 8b could intercalate into DNA through copper ion bridge to form a steady 8b-Cu(2+) -DNA ternary complex which might further block DNA replication to exert the powerful bioactivities. Study of compound 8b with human serum albumin indicated that compound 8b could be effectively stored and carried by human serum albumin.

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“…New antibiotics is a major global challenge in human-patogenic bacteria because of growing antibiotic resistance. In this context, some new sulfonamides having benzimidazole ring have been reported with their potential bactericidal and fungicidal agents against various bacterial and fungal resistant species [21][22][23].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Study of New Benzimidazole Schiff Bases Bearing P-Toluene Sulfonamide Moiety

Tunç

2019

J. Chil. Chem. Soc.

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Three new Schiff bases bearing benzimidazole and p-toluen sulfonamide moiety were synthesized. Their structures were characterized by elemental analysis, FTIR, NMR and LCMS methods. The antimicrobial properties of the compounds were also evaluated. All compounds exhibit higher antimicrobial activity against all bacteria, Schiff bases (4a-4c) shows more activity than the parent aldehyde (3). 4c displays higher antibacterial activity against P. aeruginosa compare to reference drug Sulfioxazole. The compounds were found more potent against Gram-negative than Gram positive bacteria. One more free phenyl group increase the activity in 4c, but one more phenyl ring in 4b does not.In vitro antifungal activity of the compounds was also tested on fungi C. albicans C. tropicalis and C. krusei. However, our compounds exhibit no antifungal activity against three fungi.

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A unique one-pot reaction via CC cleavage from aminomethylene benzimidazoles to access benzimidazolones with wide potentiality

Cited by 17 publications

References 28 publications

Discovery of Benzimidazole–Quinolone Hybrids as New Cleaving Agents toward Drug‐Resistant Pseudomonas aeruginosa DNA

Discovery of Benzimidazole–Quinolone Hybrids as New Cleaving Agents toward Drug‐Resistant Pseudomonas aeruginosa DNA

Design, Synthesis, and Antimicrobial Evaluation of Novel Quinolone Imidazoles and Interactions with MRSA DNA

Synthesis and Antimicrobial Study of New Benzimidazole Schiff Bases Bearing P-Toluene Sulfonamide Moiety

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