Novel aminonaphthoquinone mannich bases derived from lawsone and their copper(II) complexes: synthesis, characterization and antibacterial activity
Autor(a) principal: | |
---|---|
Data de Publicação: | 2009 |
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=S0103-50532009000400015 |
Resumo: | A series of novel Mannich bases (HL1-HL13) derived from 2-hydroxy-1,4-naphthoquinone (lawsone), substituted benzaldehydes [C6H2R¹R²R³C(O)H] and various primary amines (NH2R4, R4 = n-butyl, benzyl, allyl, 2-furfuryl), and their Cu2+ complexes, [Cu(L1)2]-[Cu(L13)2], have been synthesized and fully characterized by analytical and spectroscopic methods. The structures of complexes 1(R¹ = R² = R³ = H; R4 = Bu), 2(R¹ = R³ = H; R² = NO2; R4= Bu) and 7 (R¹ = OH; R² = R³ = H; R4= Bu) were determined by single crystal X-ray diffraction studies. All complexes crystallize in centrosymmetric space groups, with a copper atom in the inversion centre. Two L- coordinate through the naphthalen-2-olate oxygen and secondary amine-N atoms, forming six-membered chelate rings around the copper atom in a trans-N2O2 environment; spectroscopic data confirm that the other complexes exhibit similar molecular arrangement. The antimicrobial activity of all compounds has been tested on seven different strains of bacteria: Bacillus cereus, Bacillus subtilis, Escherichia coli, Enterococcus faecalis, Klebsiella pneumoniae, Pseudomonas aeruginosaand Staphylococcus aureus. In general, Mannich bases were more active than complexes, HL11(R¹ = OH; R² =H; R³ = Me; R4= Bn) and HL13(R¹ = OH; R² = H; R³ = Br; R4= Bn) being the most potent inhibitors. The MIC for the most active compound HL11against S. Coliwas 20 µmol L-1 (8 µg mL-1), better than Chloramphenicol (90 µmol L-1) and well below most values reported for other naphthoquinones. |
id |
SBQ-2_82855d333ba17fff7a3c193c961962e7 |
---|---|
oai_identifier_str |
oai:scielo:S0103-50532009000400015 |
network_acronym_str |
SBQ-2 |
network_name_str |
Journal of the Brazilian Chemical Society (Online) |
repository_id_str |
|
spelling |
Novel aminonaphthoquinone mannich bases derived from lawsone and their copper(II) complexes: synthesis, characterization and antibacterial activityaminonaphthoquinonescopper complexesMannich basescrystal structure determinationantibacterial activityA series of novel Mannich bases (HL1-HL13) derived from 2-hydroxy-1,4-naphthoquinone (lawsone), substituted benzaldehydes [C6H2R¹R²R³C(O)H] and various primary amines (NH2R4, R4 = n-butyl, benzyl, allyl, 2-furfuryl), and their Cu2+ complexes, [Cu(L1)2]-[Cu(L13)2], have been synthesized and fully characterized by analytical and spectroscopic methods. The structures of complexes 1(R¹ = R² = R³ = H; R4 = Bu), 2(R¹ = R³ = H; R² = NO2; R4= Bu) and 7 (R¹ = OH; R² = R³ = H; R4= Bu) were determined by single crystal X-ray diffraction studies. All complexes crystallize in centrosymmetric space groups, with a copper atom in the inversion centre. Two L- coordinate through the naphthalen-2-olate oxygen and secondary amine-N atoms, forming six-membered chelate rings around the copper atom in a trans-N2O2 environment; spectroscopic data confirm that the other complexes exhibit similar molecular arrangement. The antimicrobial activity of all compounds has been tested on seven different strains of bacteria: Bacillus cereus, Bacillus subtilis, Escherichia coli, Enterococcus faecalis, Klebsiella pneumoniae, Pseudomonas aeruginosaand Staphylococcus aureus. In general, Mannich bases were more active than complexes, HL11(R¹ = OH; R² =H; R³ = Me; R4= Bn) and HL13(R¹ = OH; R² = H; R³ = Br; R4= Bn) being the most potent inhibitors. The MIC for the most active compound HL11against S. Coliwas 20 µmol L-1 (8 µg mL-1), better than Chloramphenicol (90 µmol L-1) and well below most values reported for other naphthoquinones.Sociedade Brasileira de Química2009-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000400015Journal of the Brazilian Chemical Society v.20 n.4 2009reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532009000400015info:eu-repo/semantics/openAccessNeves,Amanda P.Barbosa,Cláudia C.Greco,Sandro J.Vargas,Maria D.Visentin,Lorenzo C.Pinheiro,Carlos B.Mangrich,Antônio S.Barbosa,Jussara P.Costa,Gisela L. daeng2009-06-10T00:00:00Zoai:scielo:S0103-50532009000400015Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2009-06-10T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Novel aminonaphthoquinone mannich bases derived from lawsone and their copper(II) complexes: synthesis, characterization and antibacterial activity |
title |
Novel aminonaphthoquinone mannich bases derived from lawsone and their copper(II) complexes: synthesis, characterization and antibacterial activity |
spellingShingle |
Novel aminonaphthoquinone mannich bases derived from lawsone and their copper(II) complexes: synthesis, characterization and antibacterial activity Neves,Amanda P. aminonaphthoquinones copper complexes Mannich bases crystal structure determination antibacterial activity |
title_short |
Novel aminonaphthoquinone mannich bases derived from lawsone and their copper(II) complexes: synthesis, characterization and antibacterial activity |
title_full |
Novel aminonaphthoquinone mannich bases derived from lawsone and their copper(II) complexes: synthesis, characterization and antibacterial activity |
title_fullStr |
Novel aminonaphthoquinone mannich bases derived from lawsone and their copper(II) complexes: synthesis, characterization and antibacterial activity |
title_full_unstemmed |
Novel aminonaphthoquinone mannich bases derived from lawsone and their copper(II) complexes: synthesis, characterization and antibacterial activity |
title_sort |
Novel aminonaphthoquinone mannich bases derived from lawsone and their copper(II) complexes: synthesis, characterization and antibacterial activity |
author |
Neves,Amanda P. |
author_facet |
Neves,Amanda P. Barbosa,Cláudia C. Greco,Sandro J. Vargas,Maria D. Visentin,Lorenzo C. Pinheiro,Carlos B. Mangrich,Antônio S. Barbosa,Jussara P. Costa,Gisela L. da |
author_role |
author |
author2 |
Barbosa,Cláudia C. Greco,Sandro J. Vargas,Maria D. Visentin,Lorenzo C. Pinheiro,Carlos B. Mangrich,Antônio S. Barbosa,Jussara P. Costa,Gisela L. da |
author2_role |
author author author author author author author author |
dc.contributor.author.fl_str_mv |
Neves,Amanda P. Barbosa,Cláudia C. Greco,Sandro J. Vargas,Maria D. Visentin,Lorenzo C. Pinheiro,Carlos B. Mangrich,Antônio S. Barbosa,Jussara P. Costa,Gisela L. da |
dc.subject.por.fl_str_mv |
aminonaphthoquinones copper complexes Mannich bases crystal structure determination antibacterial activity |
topic |
aminonaphthoquinones copper complexes Mannich bases crystal structure determination antibacterial activity |
description |
A series of novel Mannich bases (HL1-HL13) derived from 2-hydroxy-1,4-naphthoquinone (lawsone), substituted benzaldehydes [C6H2R¹R²R³C(O)H] and various primary amines (NH2R4, R4 = n-butyl, benzyl, allyl, 2-furfuryl), and their Cu2+ complexes, [Cu(L1)2]-[Cu(L13)2], have been synthesized and fully characterized by analytical and spectroscopic methods. The structures of complexes 1(R¹ = R² = R³ = H; R4 = Bu), 2(R¹ = R³ = H; R² = NO2; R4= Bu) and 7 (R¹ = OH; R² = R³ = H; R4= Bu) were determined by single crystal X-ray diffraction studies. All complexes crystallize in centrosymmetric space groups, with a copper atom in the inversion centre. Two L- coordinate through the naphthalen-2-olate oxygen and secondary amine-N atoms, forming six-membered chelate rings around the copper atom in a trans-N2O2 environment; spectroscopic data confirm that the other complexes exhibit similar molecular arrangement. The antimicrobial activity of all compounds has been tested on seven different strains of bacteria: Bacillus cereus, Bacillus subtilis, Escherichia coli, Enterococcus faecalis, Klebsiella pneumoniae, Pseudomonas aeruginosaand Staphylococcus aureus. In general, Mannich bases were more active than complexes, HL11(R¹ = OH; R² =H; R³ = Me; R4= Bn) and HL13(R¹ = OH; R² = H; R³ = Br; R4= Bn) being the most potent inhibitors. The MIC for the most active compound HL11against S. Coliwas 20 µmol L-1 (8 µg mL-1), better than Chloramphenicol (90 µmol L-1) and well below most values reported for other naphthoquinones. |
publishDate |
2009 |
dc.date.none.fl_str_mv |
2009-01-01 |
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=S0103-50532009000400015 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000400015 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0103-50532009000400015 |
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.20 n.4 2009 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 |
_version_ |
1750318169825738752 |