Synthesis and Anti-Staphylococcal Activity of 2,4-Disubstituted Diphenylamines

Detalhes bibliográficos
Autor(a) principal: Mehton,Ramandeep K.
Data de Publicação: 2016
Outros Autores: Meshram,Vineet, Saxena,Sanjai, Chhibber,Manmohan
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000701236
Resumo: Infections caused by Staphylococcus aureus are ubiquitous and life threatening. Evolution of resistant strains has necessitated the need to continuously discover new drugs to combat such organisms. Diphenyl ethers, such as triclosan, have recently shown potential as antibacterial agents. In this study, a series of diphenyl amines were synthesized and evaluated for in vitro antibacterial activity against Gram-positive (Staphylococcus aureus, Bacillus subtilis, Staphylococcus epidermidis) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa, Pseudomonas putida) bacteria. Preliminary results showed that six of the twelve synthesized molecules were active against Staphylococcus aureus. Most notable amongst them were compounds 2(2,4-dinitrophenylamino)phenol and 2(2-dinitrophenylamino)phenol having minimum inhibitory concentration (MIC) in the range of 7.8-15.6 µg mL-1 and 7.8-62.5 µg mL-1respectively for all the eight selected organisms. Five active compounds from the preliminary results were further screened against resistant S. aureus cultures where compounds 2(2,4-dinitrophenylamino)phenol, 2(2-dinitrophenylamino)phenol and 2-chloro-N-(2-(2,4-dichlorophenylamino)phenyl)acetamide gave encouraging results having MIC in the range 3.9-7.8 µg mL-1for most of the organisms. Results obtained above for the selected organisms and the resistant S. aureus strains conclude that hydroxyl group at 2-position of ring B potentiates the antibacterial activity and overcomes the antibiotic resistance.
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spelling Synthesis and Anti-Staphylococcal Activity of 2,4-Disubstituted Diphenylaminesinfectious diseasesenoyl-acyl carrier protein (ACP) reductasesStaphylococcus aureusresistant strainscefepimeInfections caused by Staphylococcus aureus are ubiquitous and life threatening. Evolution of resistant strains has necessitated the need to continuously discover new drugs to combat such organisms. Diphenyl ethers, such as triclosan, have recently shown potential as antibacterial agents. In this study, a series of diphenyl amines were synthesized and evaluated for in vitro antibacterial activity against Gram-positive (Staphylococcus aureus, Bacillus subtilis, Staphylococcus epidermidis) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa, Pseudomonas putida) bacteria. Preliminary results showed that six of the twelve synthesized molecules were active against Staphylococcus aureus. Most notable amongst them were compounds 2(2,4-dinitrophenylamino)phenol and 2(2-dinitrophenylamino)phenol having minimum inhibitory concentration (MIC) in the range of 7.8-15.6 µg mL-1 and 7.8-62.5 µg mL-1respectively for all the eight selected organisms. Five active compounds from the preliminary results were further screened against resistant S. aureus cultures where compounds 2(2,4-dinitrophenylamino)phenol, 2(2-dinitrophenylamino)phenol and 2-chloro-N-(2-(2,4-dichlorophenylamino)phenyl)acetamide gave encouraging results having MIC in the range 3.9-7.8 µg mL-1for most of the organisms. Results obtained above for the selected organisms and the resistant S. aureus strains conclude that hydroxyl group at 2-position of ring B potentiates the antibacterial activity and overcomes the antibiotic resistance.Sociedade Brasileira de Química2016-06-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000701236Journal of the Brazilian Chemical Society v.27 n.7 2016reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20160020info:eu-repo/semantics/openAccessMehton,Ramandeep K.Meshram,VineetSaxena,SanjaiChhibber,Manmohaneng2016-07-26T00:00:00Zoai:scielo:S0103-50532016000701236Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2016-07-26T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis and Anti-Staphylococcal Activity of 2,4-Disubstituted Diphenylamines
title Synthesis and Anti-Staphylococcal Activity of 2,4-Disubstituted Diphenylamines
spellingShingle Synthesis and Anti-Staphylococcal Activity of 2,4-Disubstituted Diphenylamines
Mehton,Ramandeep K.
infectious diseases
enoyl-acyl carrier protein (ACP) reductases
Staphylococcus aureus
resistant strains
cefepime
title_short Synthesis and Anti-Staphylococcal Activity of 2,4-Disubstituted Diphenylamines
title_full Synthesis and Anti-Staphylococcal Activity of 2,4-Disubstituted Diphenylamines
title_fullStr Synthesis and Anti-Staphylococcal Activity of 2,4-Disubstituted Diphenylamines
title_full_unstemmed Synthesis and Anti-Staphylococcal Activity of 2,4-Disubstituted Diphenylamines
title_sort Synthesis and Anti-Staphylococcal Activity of 2,4-Disubstituted Diphenylamines
author Mehton,Ramandeep K.
author_facet Mehton,Ramandeep K.
Meshram,Vineet
Saxena,Sanjai
Chhibber,Manmohan
author_role author
author2 Meshram,Vineet
Saxena,Sanjai
Chhibber,Manmohan
author2_role author
author
author
dc.contributor.author.fl_str_mv Mehton,Ramandeep K.
Meshram,Vineet
Saxena,Sanjai
Chhibber,Manmohan
dc.subject.por.fl_str_mv infectious diseases
enoyl-acyl carrier protein (ACP) reductases
Staphylococcus aureus
resistant strains
cefepime
topic infectious diseases
enoyl-acyl carrier protein (ACP) reductases
Staphylococcus aureus
resistant strains
cefepime
description Infections caused by Staphylococcus aureus are ubiquitous and life threatening. Evolution of resistant strains has necessitated the need to continuously discover new drugs to combat such organisms. Diphenyl ethers, such as triclosan, have recently shown potential as antibacterial agents. In this study, a series of diphenyl amines were synthesized and evaluated for in vitro antibacterial activity against Gram-positive (Staphylococcus aureus, Bacillus subtilis, Staphylococcus epidermidis) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa, Pseudomonas putida) bacteria. Preliminary results showed that six of the twelve synthesized molecules were active against Staphylococcus aureus. Most notable amongst them were compounds 2(2,4-dinitrophenylamino)phenol and 2(2-dinitrophenylamino)phenol having minimum inhibitory concentration (MIC) in the range of 7.8-15.6 µg mL-1 and 7.8-62.5 µg mL-1respectively for all the eight selected organisms. Five active compounds from the preliminary results were further screened against resistant S. aureus cultures where compounds 2(2,4-dinitrophenylamino)phenol, 2(2-dinitrophenylamino)phenol and 2-chloro-N-(2-(2,4-dichlorophenylamino)phenyl)acetamide gave encouraging results having MIC in the range 3.9-7.8 µg mL-1for most of the organisms. Results obtained above for the selected organisms and the resistant S. aureus strains conclude that hydroxyl group at 2-position of ring B potentiates the antibacterial activity and overcomes the antibiotic resistance.
publishDate 2016
dc.date.none.fl_str_mv 2016-06-01
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dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000701236
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dc.relation.none.fl_str_mv 10.5935/0103-5053.20160020
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dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.27 n.7 2016
reponame:Journal of the Brazilian Chemical Society (Online)
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