New 7-piperazinylquinolones containing (benzo[d]imidazol-2-yl)methyl moiety as potent antibacterial agents

Arab, Hojat-Allah; Faramarzi, Mohammad Ali; Samadi, Nasrin; Irannejad, Hamid; Foroumadi, Alireza; Emami, Saeed

doi:10.1007/s11030-018-9834-3

Cited by 6 publications

(5 citation statements)

References 30 publications

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“…The synthesis of chiral amino alcohols‐benzimidazole hybrid starts with the reaction of monochloro acetic acid and 1,2‐diaminobenzene in 4 N HCl and then N ‐tosylation of 2‐(chloromethyl)‐1‐ H ‐benzimidazole 1 with p ‐toluensulfonyl chloride in pyridine gave 2‐(Chloromethyl)‐1‐[(4‐methylphenyl)sulfonyl]‐1 H ‐benzimidazole 2 . All spectroscopic and physical data of synthesized compound 1 and 2 are consistent with the literature . (Scheme ) The chiral amino alcohols‐benzimidazole hybrid compounds were synthesized the reaction of commercially available chiral amino alcohols with the 2‐(chloromethyl)‐ N ‐tosyl‐1‐ H ‐benzimidazole 2 .…”

Section: Resultssupporting

confidence: 63%

Synthesis and Antibacterial Activity of New Chiral Aminoalcohol and Benzimidazole Hybrids

et al. 2020

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New chiral aminoalcohol‐benzimidazole hybrids have been synthesized from commercially available aminoalcohols [S(+)‐Phenylglycinol, S(−)‐ Phenylalaninol and S(+)‐ Leuicinol] and 2‐(chloromethyl)‐N‐tosyl‐1‐H‐benzimidazole. The synthesized compound were characterized by IR, NMR, and LC‐MS analysis. The antibacterial properties of aminoalcohol‐benzimidazole hybrid molecules 4 a, 4 b, and 4 c were investigated against both gram (+ve) and gram (‐ve) bacterial pathogens by the well‐diffusion method using several standarts. The cell‐based biological experiment was consistent with in silico studies. Furthermore, in silico studies revealed that all synthesized compounds could be suggested as potential drugs for inhibition of both peptide deformylase for bacteria and sterol 14α‐demethylase for yeast.

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Section: Resultssupporting

confidence: 63%

Synthesis and Antibacterial Activity of New Chiral Aminoalcohol and Benzimidazole Hybrids

et al. 2020

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“…Compound 8 showed the highest activity ylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis, and Escherichia co value of 0.097 μg/mL. Computational studies indicate the docking poses of against DNA gyrase, subunits A (PDB code: 2XCT) and subunit B (PDB cod comparable with the reference standard [73].…”

Section: To Overcome the Mdr Problem New Derivatives Of Gatifloxacin ...mentioning

confidence: 92%

DNA Gyrase as a Target for Quinolones

Spencer

Panda

2023

Biomedicines

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Bacterial DNA gyrase is a type II topoisomerase that can introduce negative supercoils to DNA substrates and is a clinically-relevant target for the development of new antibacterials. DNA gyrase is one of the primary targets of quinolones, broad-spectrum antibacterial agents and are used as a first-line drug for various types of infections. However, currently used quinolones are becoming less effective due to drug resistance. Common resistance comes in the form of mutation in enzyme targets, with this type being the most clinically relevant. Additional mechanisms, conducive to quinolone resistance, are arbitrated by chromosomal mutations and/or plasmid-gene uptake that can alter quinolone cellular concentration and interaction with the target, or affect drug metabolism. Significant synthetic strategies have been employed to modify the quinolone scaffold and/or develop novel quinolones to overcome the resistance problem. This review discusses the development of quinolone antibiotics targeting DNA gyrase to overcome bacterial resistance and reduce toxicity. Moreover, structural activity relationship (SAR) data included in this review could be useful for the development of future generations of quinolone antibiotics.

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“…[12][13][14] Developing new antibacterial agents by hybridizing two active scaffolds can lead to molecules having better inhibitory activities against the resistant bacteria. [15][16][17][18][19] Modifications of the core and substitutions are carried out on the piperazine moiety at C7 of the quinolone to develop inhibitors for resistant bacterial pathogens. In this prospect, Kulabas et al reported different aniline-linked ciprofloxacin as antibacterial and anti-mycobacterial agents, of which compound VI showed good inhibition against gram + ve and gram -ve bacteria with a MIC ranging from 1.25 to 4 μg/mL.…”

Section: Introductionmentioning

confidence: 99%

“…Diphenyl ethers like triclosan ( V ) and its derivatives are known to be potent antibacterial agents [12–14] . Developing new antibacterial agents by hybridizing two active scaffolds can lead to molecules having better inhibitory activities against the resistant bacteria [15–19] …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Diphenyl Ether‐Linked Quinolone Derivatives as Antibacterial Agents

Ghouse,

Akhir,

Sinha

et al. 2023

ChemistrySelect

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The increase in the prevalence of multi‐drug‐resistant bacteria poses a significant healthcare challenge. The urgent need to combat the resistant microbes necessitates discovering new antibacterial agents capable of circumventing the existing resistance mechanisms. Targeting DNA gyrase by suitably modifying the fluoroquinolones can lead to antibiotics with better activity and lower incidence of resistance. The substituted diphenyl ethers like triclosan are known to have potent antibacterial activity. In the current study, the hybridisation of diphenyl ether moiety with fluoroquinolones led to the design and synthesis of new compounds with potent inhibitory activity against staphylococcus aureus with MIC 0.5–64 μg/mL and moderately active against mycobacteria with MIC 2–64 μg/mL. The compounds are non‐toxic to Vero cells with a selectivity index >10 to 200. The compounds also inhibited the resistant strains of S. aureus with a MIC ranging from 0.5–64 μg/mL. The synthesised compounds also exhibited potent anti‐biofilm activity against S. aureus. Furthermore, the DNA supercoiling assay revealed the compounds 7 i, 7 o, 7 p and 7 q showed concentration‐dependant DNA‐Gyrase inhibition at 1 μg/mL.

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New 7-piperazinylquinolones containing (benzo[d]imidazol-2-yl)methyl moiety as potent antibacterial agents

Cited by 6 publications

References 30 publications

Synthesis and Antibacterial Activity of New Chiral Aminoalcohol and Benzimidazole Hybrids

Synthesis and Antibacterial Activity of New Chiral Aminoalcohol and Benzimidazole Hybrids

DNA Gyrase as a Target for Quinolones

Synthesis and Biological Evaluation of Diphenyl Ether‐Linked Quinolone Derivatives as Antibacterial Agents

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