A new approach for the synthesis of bioactive heteroaryl thiazolidine-2,4-diones
Autor(a) principal: | |
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Data de Publicação: | 2011 |
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=S0103-50532011000600019 |
Resumo: | Condensation of 3-formylchromone (1) with thiazolidine-2,4-dione (2) afforded 5-[4-oxo-4H-chromen-3-yl)methylene]-1,3-thiazolidine-2,4-dione (3). Reaction of 3 with hydrazine hydrate, phenyl hydrazine and hydroxylamine hydrochloride gave the corresponding pyrazole and isoxazole derivatives 4-7. Compound 3 was subjected to react with thiourea, guanidine and cyanoguanidine to give the corresponding pyrimidine derivatives 8-10. Pyrimido[1,2-a]pyrimidine 12, benzo[1,5]diazepine 15, pyrido[1,2-b][1,2,4]triazepine 16, 1,2,4-triazolo[3,4-b][1,3,4]thiadiazepine 19 and 1,2,4-triazino[3,2-b][1,3,4]thiadiazepine 20 linked thiazolidine-2,4-dione were prepared from the reaction of 3 with N,N- and N,S- bifunctional nucleophiles. The chemical reactivity of 3 towards carbon nucleophiles gave new heterocyclic moieties linked thiazolidine-2,4-dione 22‑25. The synthesized compounds were screened in vitro for their antimicrobial activities against Staphylococcus aureus, Proteus vulgaris and Candida albicans. |
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A new approach for the synthesis of bioactive heteroaryl thiazolidine-2,4-diones2,4-thiazolidinedionechromoneMichael additioncyclocondensationRORCheterocyclic synthesisCondensation of 3-formylchromone (1) with thiazolidine-2,4-dione (2) afforded 5-[4-oxo-4H-chromen-3-yl)methylene]-1,3-thiazolidine-2,4-dione (3). Reaction of 3 with hydrazine hydrate, phenyl hydrazine and hydroxylamine hydrochloride gave the corresponding pyrazole and isoxazole derivatives 4-7. Compound 3 was subjected to react with thiourea, guanidine and cyanoguanidine to give the corresponding pyrimidine derivatives 8-10. Pyrimido[1,2-a]pyrimidine 12, benzo[1,5]diazepine 15, pyrido[1,2-b][1,2,4]triazepine 16, 1,2,4-triazolo[3,4-b][1,3,4]thiadiazepine 19 and 1,2,4-triazino[3,2-b][1,3,4]thiadiazepine 20 linked thiazolidine-2,4-dione were prepared from the reaction of 3 with N,N- and N,S- bifunctional nucleophiles. The chemical reactivity of 3 towards carbon nucleophiles gave new heterocyclic moieties linked thiazolidine-2,4-dione 22‑25. The synthesized compounds were screened in vitro for their antimicrobial activities against Staphylococcus aureus, Proteus vulgaris and Candida albicans.Sociedade Brasileira de Química2011-06-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532011000600019Journal of the Brazilian Chemical Society v.22 n.6 2011reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532011000600019info:eu-repo/semantics/openAccessIbrahim,Magdy AhmedAbdel-Hamed,Mohamed Abdel-MegidEl-Gohary,Naser Mohamedeng2011-06-10T00:00:00Zoai:scielo:S0103-50532011000600019Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2011-06-10T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
A new approach for the synthesis of bioactive heteroaryl thiazolidine-2,4-diones |
title |
A new approach for the synthesis of bioactive heteroaryl thiazolidine-2,4-diones |
spellingShingle |
A new approach for the synthesis of bioactive heteroaryl thiazolidine-2,4-diones Ibrahim,Magdy Ahmed 2,4-thiazolidinedione chromone Michael addition cyclocondensation RORC heterocyclic synthesis |
title_short |
A new approach for the synthesis of bioactive heteroaryl thiazolidine-2,4-diones |
title_full |
A new approach for the synthesis of bioactive heteroaryl thiazolidine-2,4-diones |
title_fullStr |
A new approach for the synthesis of bioactive heteroaryl thiazolidine-2,4-diones |
title_full_unstemmed |
A new approach for the synthesis of bioactive heteroaryl thiazolidine-2,4-diones |
title_sort |
A new approach for the synthesis of bioactive heteroaryl thiazolidine-2,4-diones |
author |
Ibrahim,Magdy Ahmed |
author_facet |
Ibrahim,Magdy Ahmed Abdel-Hamed,Mohamed Abdel-Megid El-Gohary,Naser Mohamed |
author_role |
author |
author2 |
Abdel-Hamed,Mohamed Abdel-Megid El-Gohary,Naser Mohamed |
author2_role |
author author |
dc.contributor.author.fl_str_mv |
Ibrahim,Magdy Ahmed Abdel-Hamed,Mohamed Abdel-Megid El-Gohary,Naser Mohamed |
dc.subject.por.fl_str_mv |
2,4-thiazolidinedione chromone Michael addition cyclocondensation RORC heterocyclic synthesis |
topic |
2,4-thiazolidinedione chromone Michael addition cyclocondensation RORC heterocyclic synthesis |
description |
Condensation of 3-formylchromone (1) with thiazolidine-2,4-dione (2) afforded 5-[4-oxo-4H-chromen-3-yl)methylene]-1,3-thiazolidine-2,4-dione (3). Reaction of 3 with hydrazine hydrate, phenyl hydrazine and hydroxylamine hydrochloride gave the corresponding pyrazole and isoxazole derivatives 4-7. Compound 3 was subjected to react with thiourea, guanidine and cyanoguanidine to give the corresponding pyrimidine derivatives 8-10. Pyrimido[1,2-a]pyrimidine 12, benzo[1,5]diazepine 15, pyrido[1,2-b][1,2,4]triazepine 16, 1,2,4-triazolo[3,4-b][1,3,4]thiadiazepine 19 and 1,2,4-triazino[3,2-b][1,3,4]thiadiazepine 20 linked thiazolidine-2,4-dione were prepared from the reaction of 3 with N,N- and N,S- bifunctional nucleophiles. The chemical reactivity of 3 towards carbon nucleophiles gave new heterocyclic moieties linked thiazolidine-2,4-dione 22‑25. The synthesized compounds were screened in vitro for their antimicrobial activities against Staphylococcus aureus, Proteus vulgaris and Candida albicans. |
publishDate |
2011 |
dc.date.none.fl_str_mv |
2011-06-01 |
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=S0103-50532011000600019 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532011000600019 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0103-50532011000600019 |
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.22 n.6 2011 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_ |
1750318172303523840 |