Synthesis, characterization and biological activity of 2-methyl-3-aminoquinazolin-4(3H)-ones Schiff bases
Autor(a) principal: | |
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Data de Publicação: | 2008 |
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=S0103-50532008000500023 |
Resumo: | The 3-amino-2-methylquinazoline/6-bromo-2-methylquinazoline-4(3H)-ones, 2a,b, on treatment with 2,3-indolinedione in the presence of traces of glacial acetic acid yielded 3-{(2'-oxo-1',2'-dihydroindole-3'-ylidene)amino} -2-methylquinazolin/6-bromo-2-methylquinazolin-4-(3H)-ones, 3a,b, which on condensation with various secondary amines and formaldehyde in ethanol afforded title compounds 3-{(1'-alkyl/arylaminomethyl-2'-oxo-1',2'-dihydroindole-3'-ylidene)amino} -2-methyl-6-quinazolin-4-(3H)-ones, 4a1-6 and 4b1-6. C, H, N analysis, infrared spectroscopy, ¹H NMR, and mass spectroscopy allowed the identification of the synthesized compounds, which were investigated for their antimicrobial, analgesic, anti-inflammatory and antihelmintic activities. The results of the biological activities revealed that the compounds 4a3, 4a4 and 4b6 exhibited significant analgesic and anti-inflammatory activities. Compounds 4b5 and 4b6 showed antihelmintic activity when tested against Pheretima posthuma. |
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Synthesis, characterization and biological activity of 2-methyl-3-aminoquinazolin-4(3H)-ones Schiff bases2-methylquinazolin-4(3H)-onebromoderivative2,3-indolinedioneMannich baseantimicrobialThe 3-amino-2-methylquinazoline/6-bromo-2-methylquinazoline-4(3H)-ones, 2a,b, on treatment with 2,3-indolinedione in the presence of traces of glacial acetic acid yielded 3-{(2'-oxo-1',2'-dihydroindole-3'-ylidene)amino} -2-methylquinazolin/6-bromo-2-methylquinazolin-4-(3H)-ones, 3a,b, which on condensation with various secondary amines and formaldehyde in ethanol afforded title compounds 3-{(1'-alkyl/arylaminomethyl-2'-oxo-1',2'-dihydroindole-3'-ylidene)amino} -2-methyl-6-quinazolin-4-(3H)-ones, 4a1-6 and 4b1-6. C, H, N analysis, infrared spectroscopy, ¹H NMR, and mass spectroscopy allowed the identification of the synthesized compounds, which were investigated for their antimicrobial, analgesic, anti-inflammatory and antihelmintic activities. The results of the biological activities revealed that the compounds 4a3, 4a4 and 4b6 exhibited significant analgesic and anti-inflammatory activities. Compounds 4b5 and 4b6 showed antihelmintic activity when tested against Pheretima posthuma.Sociedade Brasileira de Química2008-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532008000500023Journal of the Brazilian Chemical Society v.19 n.5 2008reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532008000500023info:eu-repo/semantics/openAccessSahu,S. K.Azam,Md. AfzalBanerjee,M.Acharrya,S.Behera,C. C.Si,S.eng2008-08-05T00:00:00Zoai:scielo:S0103-50532008000500023Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2008-08-05T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Synthesis, characterization and biological activity of 2-methyl-3-aminoquinazolin-4(3H)-ones Schiff bases |
title |
Synthesis, characterization and biological activity of 2-methyl-3-aminoquinazolin-4(3H)-ones Schiff bases |
spellingShingle |
Synthesis, characterization and biological activity of 2-methyl-3-aminoquinazolin-4(3H)-ones Schiff bases Sahu,S. K. 2-methylquinazolin-4(3H)-one bromoderivative 2,3-indolinedione Mannich base antimicrobial |
title_short |
Synthesis, characterization and biological activity of 2-methyl-3-aminoquinazolin-4(3H)-ones Schiff bases |
title_full |
Synthesis, characterization and biological activity of 2-methyl-3-aminoquinazolin-4(3H)-ones Schiff bases |
title_fullStr |
Synthesis, characterization and biological activity of 2-methyl-3-aminoquinazolin-4(3H)-ones Schiff bases |
title_full_unstemmed |
Synthesis, characterization and biological activity of 2-methyl-3-aminoquinazolin-4(3H)-ones Schiff bases |
title_sort |
Synthesis, characterization and biological activity of 2-methyl-3-aminoquinazolin-4(3H)-ones Schiff bases |
author |
Sahu,S. K. |
author_facet |
Sahu,S. K. Azam,Md. Afzal Banerjee,M. Acharrya,S. Behera,C. C. Si,S. |
author_role |
author |
author2 |
Azam,Md. Afzal Banerjee,M. Acharrya,S. Behera,C. C. Si,S. |
author2_role |
author author author author author |
dc.contributor.author.fl_str_mv |
Sahu,S. K. Azam,Md. Afzal Banerjee,M. Acharrya,S. Behera,C. C. Si,S. |
dc.subject.por.fl_str_mv |
2-methylquinazolin-4(3H)-one bromoderivative 2,3-indolinedione Mannich base antimicrobial |
topic |
2-methylquinazolin-4(3H)-one bromoderivative 2,3-indolinedione Mannich base antimicrobial |
description |
The 3-amino-2-methylquinazoline/6-bromo-2-methylquinazoline-4(3H)-ones, 2a,b, on treatment with 2,3-indolinedione in the presence of traces of glacial acetic acid yielded 3-{(2'-oxo-1',2'-dihydroindole-3'-ylidene)amino} -2-methylquinazolin/6-bromo-2-methylquinazolin-4-(3H)-ones, 3a,b, which on condensation with various secondary amines and formaldehyde in ethanol afforded title compounds 3-{(1'-alkyl/arylaminomethyl-2'-oxo-1',2'-dihydroindole-3'-ylidene)amino} -2-methyl-6-quinazolin-4-(3H)-ones, 4a1-6 and 4b1-6. C, H, N analysis, infrared spectroscopy, ¹H NMR, and mass spectroscopy allowed the identification of the synthesized compounds, which were investigated for their antimicrobial, analgesic, anti-inflammatory and antihelmintic activities. The results of the biological activities revealed that the compounds 4a3, 4a4 and 4b6 exhibited significant analgesic and anti-inflammatory activities. Compounds 4b5 and 4b6 showed antihelmintic activity when tested against Pheretima posthuma. |
publishDate |
2008 |
dc.date.none.fl_str_mv |
2008-01-01 |
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=S0103-50532008000500023 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532008000500023 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0103-50532008000500023 |
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.19 n.5 2008 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_ |
1750318169018335232 |