Design, Synthesis and Antitubercular Activity of 2-(Benzylthio)-1H-benzo[d]imidazoles
Autor(a) principal: | |
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Data de Publicação: | 2021 |
Outros Autores: | , , , , , , , |
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=S0103-50532021000701413 |
Resumo: | Using molecular simplification and molecular hybridization approaches, a series of 2-(benzylthio)-1H-benzo[d]imidazoles was synthesized and evaluated as in vitro inhibitors of Mycobacterium tuberculosis (M. tuberculosis) growth. Compounds 6p and 6z were considered the lead compounds from this series of molecules, with minimal inhibitory concentration (MIC) values of 6.9 and 3.8 µM against M. tuberculosis H37Rv, respectively. Additionally, the leading compounds were active against multidrug-resistant strains and were devoid of apparent toxicity to Vero and HepG2 cells, from 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and neutral red assays. Finally, the compounds presented good aqueous solubility and high plasma stability. These data together indicate that this class of molecules may furnish new anti-tuberculosis drug candidates for future development. |
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Design, Synthesis and Antitubercular Activity of 2-(Benzylthio)-1H-benzo[d]imidazolesMycobacterium tuberculosistuberculosisdrug-resistant strainpreliminary SAR studyUsing molecular simplification and molecular hybridization approaches, a series of 2-(benzylthio)-1H-benzo[d]imidazoles was synthesized and evaluated as in vitro inhibitors of Mycobacterium tuberculosis (M. tuberculosis) growth. Compounds 6p and 6z were considered the lead compounds from this series of molecules, with minimal inhibitory concentration (MIC) values of 6.9 and 3.8 µM against M. tuberculosis H37Rv, respectively. Additionally, the leading compounds were active against multidrug-resistant strains and were devoid of apparent toxicity to Vero and HepG2 cells, from 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and neutral red assays. Finally, the compounds presented good aqueous solubility and high plasma stability. These data together indicate that this class of molecules may furnish new anti-tuberculosis drug candidates for future development.Sociedade Brasileira de Química2021-07-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000701413Journal of the Brazilian Chemical Society v.32 n.7 2021reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20210040info:eu-repo/semantics/openAccessRambo,Raoní S.Waldow,Etienne C.Abaddi,Bruno L.Silveira,Maiele D.Dadda,Adilio S.Sperotto,NathaliaBizarro,Cristiano V.Augusto,LuizMachado,Pabloeng2021-06-30T00:00:00Zoai:scielo:S0103-50532021000701413Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2021-06-30T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Design, Synthesis and Antitubercular Activity of 2-(Benzylthio)-1H-benzo[d]imidazoles |
title |
Design, Synthesis and Antitubercular Activity of 2-(Benzylthio)-1H-benzo[d]imidazoles |
spellingShingle |
Design, Synthesis and Antitubercular Activity of 2-(Benzylthio)-1H-benzo[d]imidazoles Rambo,Raoní S. Mycobacterium tuberculosis tuberculosis drug-resistant strain preliminary SAR study |
title_short |
Design, Synthesis and Antitubercular Activity of 2-(Benzylthio)-1H-benzo[d]imidazoles |
title_full |
Design, Synthesis and Antitubercular Activity of 2-(Benzylthio)-1H-benzo[d]imidazoles |
title_fullStr |
Design, Synthesis and Antitubercular Activity of 2-(Benzylthio)-1H-benzo[d]imidazoles |
title_full_unstemmed |
Design, Synthesis and Antitubercular Activity of 2-(Benzylthio)-1H-benzo[d]imidazoles |
title_sort |
Design, Synthesis and Antitubercular Activity of 2-(Benzylthio)-1H-benzo[d]imidazoles |
author |
Rambo,Raoní S. |
author_facet |
Rambo,Raoní S. Waldow,Etienne C. Abaddi,Bruno L. Silveira,Maiele D. Dadda,Adilio S. Sperotto,Nathalia Bizarro,Cristiano V. Augusto,Luiz Machado,Pablo |
author_role |
author |
author2 |
Waldow,Etienne C. Abaddi,Bruno L. Silveira,Maiele D. Dadda,Adilio S. Sperotto,Nathalia Bizarro,Cristiano V. Augusto,Luiz Machado,Pablo |
author2_role |
author author author author author author author author |
dc.contributor.author.fl_str_mv |
Rambo,Raoní S. Waldow,Etienne C. Abaddi,Bruno L. Silveira,Maiele D. Dadda,Adilio S. Sperotto,Nathalia Bizarro,Cristiano V. Augusto,Luiz Machado,Pablo |
dc.subject.por.fl_str_mv |
Mycobacterium tuberculosis tuberculosis drug-resistant strain preliminary SAR study |
topic |
Mycobacterium tuberculosis tuberculosis drug-resistant strain preliminary SAR study |
description |
Using molecular simplification and molecular hybridization approaches, a series of 2-(benzylthio)-1H-benzo[d]imidazoles was synthesized and evaluated as in vitro inhibitors of Mycobacterium tuberculosis (M. tuberculosis) growth. Compounds 6p and 6z were considered the lead compounds from this series of molecules, with minimal inhibitory concentration (MIC) values of 6.9 and 3.8 µM against M. tuberculosis H37Rv, respectively. Additionally, the leading compounds were active against multidrug-resistant strains and were devoid of apparent toxicity to Vero and HepG2 cells, from 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and neutral red assays. Finally, the compounds presented good aqueous solubility and high plasma stability. These data together indicate that this class of molecules may furnish new anti-tuberculosis drug candidates for future development. |
publishDate |
2021 |
dc.date.none.fl_str_mv |
2021-07-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000701413 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000701413 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.21577/0103-5053.20210040 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
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.32 n.7 2021 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
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1750318184365293568 |