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dc.creatorBogdanović, Aleksandra
dc.creatorLazić, Anita
dc.creatorGrujic, Slavica
dc.creatorDimkic, Ivica
dc.creatorStankovic, Slavisa
dc.creatorPetrović, Slobodan
dc.date.accessioned2022-03-04T11:23:42Z
dc.date.available2022-03-04T11:23:42Z
dc.date.issued2021
dc.identifier.issn0004-1254
dc.identifier.urihttp://TechnoRep.tmf.bg.ac.rs/handle/123456789/4912
dc.description.abstractIn this study we screened twelve newly synthesised N-(substituted phenyl)-2-chloroacetamides for antimicrobial potential relying on quantitative structure-activity relationship (QSAR) analysis based on the available cheminformatics prediction models (Molinspiration, SwissADME, PreADMET, and PkcSM) and verified it through standard antimicrobial testing against Escherichia coli, Staphylococcus aureus, methicillin-resistant S. aureus (MRSA), and Candida albicans. Our compounds met all the screening criteria of Lipinski's rule of five (Ro5) as well as Veber's and Egan's methods for predicting biological activity. In antimicrobial activity tests, all chloroacetamides were effective against Gram-positive S. aureus and MRSA, less effective against the Gram-negative E. coli, and moderately effective against the yeast C. albicans. Our study confirmed that the biological activity of chloroacetamides varied with the position of substituents bound to the phenyl ring, which explains why some molecules were more effective against Gram-negative than Gram-positive bacteria or C. albicans. Bearing the halogenated p-substituted phenyl ring, N-(4-chlorophenyl), N-(4-fluorophenyl), and N-(3-bromophenyl) chloroacetamides were among the most active thanks to high lipophilicity, which allows them to pass rapidly through the phospholipid bilayer of the cell membrane. They are the most promising compounds for further investigation, particularly against Gram-positive bacteria and pathogenic yeasts.en
dc.relationinfo:eu-repo/grantAgreement/MESTD/inst-2020/200135/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/inst-2020/200178/RS//
dc.rightsopenAccess
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/
dc.sourceArhiv Za Higijenu Rada I Toksikologiju-Archives of Industrial Hygiene and Toxicology
dc.subjectN-substituted amidesen
dc.subjectantimicrobial potentialen
dc.subjectquantitative analysis of chemical structure and activity relationshipen
dc.titleCharacterisation of twelve newly synthesised N-(substituted phenyl)-2-chloroacetamides with QSAR analysis and antimicrobial activity testsen
dc.typearticle
dc.rights.licenseBY-NC-ND
dc.citation.epage79
dc.citation.issue1
dc.citation.other72(1): 70-79
dc.citation.rankM22~
dc.citation.spage70
dc.citation.volume72
dc.identifier.doi10.2478/aiht-2021-72-3483
dc.identifier.fulltexthttp://TechnoRep.tmf.bg.ac.rs/bitstream/id/7331/4908.pdf
dc.identifier.pmid33787186
dc.identifier.rcubconv_6104
dc.identifier.scopus2-s2.0-85103608918
dc.identifier.wos000657362500009
dc.type.versionpublishedVersion


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