Quinazolinone Azolyl Ethanols: Potential Lead Antimicrobial Agents with Dual Action Modes Targeting Methicillin-Resistant
            <i>Staphylococcus Aureus</i>
            DNA

Peng, Xin-Mei; Peng, Liping; Li, Shuo; Avula, Srinivasa Rao; Kannekanti, Vijaya Kumar; Zhang, Shaolin; Tam, Kin Yip; Zhou, Cheng‐He

doi:10.4155/fmc-2016-0002

Cited by 55 publications

(21 citation statements)

References 46 publications

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“…18,19 Some nonclinical hydroxyethyl azoles have also been developed with superior antibacterial or antifungal potencies. 20,21 These researches clearly demonstrated the enormous potentiality of hydroxyethyl azole in the antimicrobial aspect.…”

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confidence: 95%

Potential Antimicrobial Isopropanol-Conjugated Carbazole Azoles as Dual Targeting Inhibitors of Enterococcus faecalis

Zhang

Tangadanchu

Cheng

et al. 2018

ACS Med. Chem. Lett.

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A series of isopropanol-bridged carbazole azoles as potential antimicrobial agents were designed and synthesized from commercial carbazoles. Bioassay revealed that 3,6-dichlorocarbazolyl triazole 3f could effectively inhibit the growth of E. faecalis with minimal inhibitory concentration of 2 μg/mL. The active molecule 3f showed lower propensity to trigger the development of resistance in bacteria than norfloxacin and exerted rapidly bactericidal ability. Compound 3f also exhibited low cytotoxicity to normal mammalian RAW264.7 cells. Further mechanism exploration indicated that conjugate 3f was membrane active against E. faecalis and could form 3f−DNA complex by intercalating into DNA of resistant E. faecalis, which might be responsible for its antimicrobial action. Molecular docking showed an efficient binding of triazole derivative 3f with DNA gyrase enzyme through noncovalent interactions.

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confidence: 95%

Potential Antimicrobial Isopropanol-Conjugated Carbazole Azoles as Dual Targeting Inhibitors of Enterococcus faecalis

Zhang

Tangadanchu

Cheng

et al. 2018

ACS Med. Chem. Lett.

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“…87 Various azolyl ethanol fragments such as imidazolyl, triazolyl, tetrazolyl, benzoimidazolyl, and benzotriazolyl were incorporated at the 3 rd position of quinazolin-4(3H)one by Peng et al to get a series of hybrid analogues as potent antimicrobial agents. 88 These synthesized analogues were screened for in vitro anti-bacterial activity against Gram-positive (Micrococcus luteus ATCC4698, MRSA, Staphylococcus aureus ATCC25923, and Bacillus subtilis ATCC6633) and Gram-negative strains of bacteria (Pseudomonas aeruginosa ATCC27853, Escherichia coli DH52, Bacillus proteus ATCC13315, and Eberthella typhosa ATCC14028). Amongst the synthesized hybrid analogues, triazolyl ethanol hybrids were found to effectively inhibit all the bacterial strains, except for P. aeruginosa, and their activities were comparable or even superior than that of noroxacin (MIC of 8 mg mL À1 ) and chloromycin (MIC of 16 mg mL À1 ) against MRSA.…”

Section: Anti-microbial Hybridsmentioning

confidence: 99%

Recent advances in the pharmacological diversification of quinazoline/quinazolinone hybrids

2020

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“…Hybrids 28a,b (MIC: 8.0–16 µg/ml, two‐fold serial dilution technique) were not inferior to chloromycin (MIC: 8.0–32 µg/ml) against Gram‐positive bacteria S. aureus , MRSA, M. luteus , and B. subtilis , and the SAR indicated that the fluoro group was better than the chloro group at the C‐7 position of quinazolinone moiety. [ 72 ] Molecular docking study revealed that hybrid 28a could interact with MRSA DNA by the formation of hydrogen bonds and intercalate into MRSA DNA to form hybrid 28a –DNA complex. Moreover, DNA cleavage properties of hybrid 28a –Cu 2+ and 28a –Zn 2+ complexes were confirmed by agarose gel electrophoresis experiments.…”

Section: Miscellaneous 124‐triazole Hybridsmentioning

confidence: 99%

1,2,4‐Triazole hybrids with potential antibacterial activity against methicillin‐resistant Staphylococcus aureus

2020

Archiv der Pharmazie

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Methicillin‐resistant Staphylococcus aureus (MRSA) has developed numerous mechanisms of virulence and strategies to evade the human immune system, and it can be transmitted between humans, animals, and the environment. Thus, MRSA is an important cause of morbidity and mortality in both hospitals and in the community, creating an urgent demand for the development of novel anti‐MRSA candidates. The 1,2,4‐triazole nucleus is a bioisostere of amide, ester, and carboxylic acid, and the 1,2,4‐triazole ring is found in many compounds with diverse biological effects. 1,2,4‐Triazole derivatives could exert their antibacterial activity through inhibition of efflux pumps, filamentous temperature‐sensitive protein Z, penicillin‐binding protein, DNA gyrase, and topoisomerase IV, and they play an important role in the discovery of novel antibacterial agents. Among them, 1,2,4‐triazole hybrids, which have the potential to exert dual/multiple mechanisms of action, possess a promising broad‐spectrum antibacterial activity against a panel of clinically important drug‐resistant pathogens including MRSA. This review outlines the recent developments of 1,2,4‐triazole hybrids with a potential anti‐MRSA activity, covering articles published between 2010 and 2020. The mechanisms of action, critical aspects of their design, and structure–activity relationships are also discussed.

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Quinazolinone Azolyl Ethanols: Potential Lead Antimicrobial Agents with Dual Action Modes Targeting Methicillin-Resistant Staphylococcus Aureus DNA

Abstract: Compound 3a should be a potential lead antibacterial molecule with dual action modes.

Cited by 55 publications

References 46 publications

Potential Antimicrobial Isopropanol-Conjugated Carbazole Azoles as Dual Targeting Inhibitors of Enterococcus faecalis

Potential Antimicrobial Isopropanol-Conjugated Carbazole Azoles as Dual Targeting Inhibitors of Enterococcus faecalis

Recent advances in the pharmacological diversification of quinazoline/quinazolinone hybrids

1,2,4‐Triazole hybrids with potential antibacterial activity against methicillin‐resistant Staphylococcus aureus

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