Synthesis, characterization and biological activity of 2-methyl-3-aminoquinazolin-4(3H)-ones Schiff bases

Detalhes bibliográficos
Autor(a) principal: Sahu,S. K.
Data de Publicação: 2008
Outros Autores: Azam,Md. Afzal, Banerjee,M., Acharrya,S., Behera,C. C., Si,S.
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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spelling 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
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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
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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)
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instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
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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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