Palladium-catalysed amination of electron-deficient or relatively electron-rich benzo[b]thienyl bromides - Preliminary studies of antimicrobial activity and SARs
Autor(a) principal: | |
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Data de Publicação: | 2004 |
Outros Autores: | , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10198/820 |
Resumo: | Several diarylamines in the benzo[b]thiophene series were prepared in good to high yields by palladium-catalysed amination of ethyl 3-bromobenzo[b]thiophene-2-carboxylate with anilines and 5-aminoindole in the presence of Pd(OAc)2, BINAP and Cs2CO3 in toluene. The presence of the ester group at the 2-position of the benzo[b]thiophene moiety increases the yields and lowers the heating times relative to the reactions performed with 3-bromobenzo[b]thiophene. When aminopyridines were used instead of anilines, the ligand and the solvent need to be changed to XANTHPHOS and dioxane in the amination reaction. With 2-aminopyridine a onepot C−N coupling and intramolecular cyclization involving the nitrogen atom of the pyridine ring occurred, with loss of ethanol, giving an interesting fluorescent tetracyclic heteroaromatic compound. The antimicrobial activity, the minimal inhibitory concentrations (MICs) and the structure-activity relationships (SARs) were evaluated. A selectivity with low MICs was observed against Bacillus Cereus, and good results were also obtained against Candida albicans. The acids obtained by hydrolysis of the ester group, as non-proteinogenic α,β-unsaturated β-amino acids, can be incorporated into peptide chains to induce conformational constraints. |
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Palladium-catalysed amination of electron-deficient or relatively electron-rich benzo[b]thienyl bromides - Preliminary studies of antimicrobial activity and SARsAminationAntimicrobial activityBenzothiophenesDiarylaminesFluorescencePalladiumSeveral diarylamines in the benzo[b]thiophene series were prepared in good to high yields by palladium-catalysed amination of ethyl 3-bromobenzo[b]thiophene-2-carboxylate with anilines and 5-aminoindole in the presence of Pd(OAc)2, BINAP and Cs2CO3 in toluene. The presence of the ester group at the 2-position of the benzo[b]thiophene moiety increases the yields and lowers the heating times relative to the reactions performed with 3-bromobenzo[b]thiophene. When aminopyridines were used instead of anilines, the ligand and the solvent need to be changed to XANTHPHOS and dioxane in the amination reaction. With 2-aminopyridine a onepot C−N coupling and intramolecular cyclization involving the nitrogen atom of the pyridine ring occurred, with loss of ethanol, giving an interesting fluorescent tetracyclic heteroaromatic compound. The antimicrobial activity, the minimal inhibitory concentrations (MICs) and the structure-activity relationships (SARs) were evaluated. A selectivity with low MICs was observed against Bacillus Cereus, and good results were also obtained against Candida albicans. The acids obtained by hydrolysis of the ester group, as non-proteinogenic α,β-unsaturated β-amino acids, can be incorporated into peptide chains to induce conformational constraints.Wiley IntersicenceBiblioteca Digital do IPBQueiroz, Maria João R.P.Begouin, AgatheFerreira, Isabel C.F.R.Kirsch, GilbertCalhelha, Ricardo C.Barbosa, SandraEstevinho, Leticia M.2008-09-12T13:25:40Z20042004-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10198/820engQueiroz, Maria João R.P.; Begouin, Agathe; Ferreira, Isabel C.F.R.; Kirsch, Gilbert; Calhelha, Ricardo C.; Barbosa, Sandra; Estevinho, Leticia M. (2004). Palladium-catalysed amination of electron-deficient or relatively electron-rich benzo[b]thienyl bromides - Preliminary studies of antimicrobial activity and SARs. European Journal of Organic Chemistry. ISSN 1434-193X. 2004:4, p. 3679-36851434-193X10.1002/ejoc.200400218info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-01-16T12:04:48ZPortal AgregadorONG |
dc.title.none.fl_str_mv |
Palladium-catalysed amination of electron-deficient or relatively electron-rich benzo[b]thienyl bromides - Preliminary studies of antimicrobial activity and SARs |
title |
Palladium-catalysed amination of electron-deficient or relatively electron-rich benzo[b]thienyl bromides - Preliminary studies of antimicrobial activity and SARs |
spellingShingle |
Palladium-catalysed amination of electron-deficient or relatively electron-rich benzo[b]thienyl bromides - Preliminary studies of antimicrobial activity and SARs Queiroz, Maria João R.P. Amination Antimicrobial activity Benzothiophenes Diarylamines Fluorescence Palladium |
title_short |
Palladium-catalysed amination of electron-deficient or relatively electron-rich benzo[b]thienyl bromides - Preliminary studies of antimicrobial activity and SARs |
title_full |
Palladium-catalysed amination of electron-deficient or relatively electron-rich benzo[b]thienyl bromides - Preliminary studies of antimicrobial activity and SARs |
title_fullStr |
Palladium-catalysed amination of electron-deficient or relatively electron-rich benzo[b]thienyl bromides - Preliminary studies of antimicrobial activity and SARs |
title_full_unstemmed |
Palladium-catalysed amination of electron-deficient or relatively electron-rich benzo[b]thienyl bromides - Preliminary studies of antimicrobial activity and SARs |
title_sort |
Palladium-catalysed amination of electron-deficient or relatively electron-rich benzo[b]thienyl bromides - Preliminary studies of antimicrobial activity and SARs |
author |
Queiroz, Maria João R.P. |
author_facet |
Queiroz, Maria João R.P. Begouin, Agathe Ferreira, Isabel C.F.R. Kirsch, Gilbert Calhelha, Ricardo C. Barbosa, Sandra Estevinho, Leticia M. |
author_role |
author |
author2 |
Begouin, Agathe Ferreira, Isabel C.F.R. Kirsch, Gilbert Calhelha, Ricardo C. Barbosa, Sandra Estevinho, Leticia M. |
author2_role |
author author author author author author |
dc.contributor.none.fl_str_mv |
Biblioteca Digital do IPB |
dc.contributor.author.fl_str_mv |
Queiroz, Maria João R.P. Begouin, Agathe Ferreira, Isabel C.F.R. Kirsch, Gilbert Calhelha, Ricardo C. Barbosa, Sandra Estevinho, Leticia M. |
dc.subject.por.fl_str_mv |
Amination Antimicrobial activity Benzothiophenes Diarylamines Fluorescence Palladium |
topic |
Amination Antimicrobial activity Benzothiophenes Diarylamines Fluorescence Palladium |
description |
Several diarylamines in the benzo[b]thiophene series were prepared in good to high yields by palladium-catalysed amination of ethyl 3-bromobenzo[b]thiophene-2-carboxylate with anilines and 5-aminoindole in the presence of Pd(OAc)2, BINAP and Cs2CO3 in toluene. The presence of the ester group at the 2-position of the benzo[b]thiophene moiety increases the yields and lowers the heating times relative to the reactions performed with 3-bromobenzo[b]thiophene. When aminopyridines were used instead of anilines, the ligand and the solvent need to be changed to XANTHPHOS and dioxane in the amination reaction. With 2-aminopyridine a onepot C−N coupling and intramolecular cyclization involving the nitrogen atom of the pyridine ring occurred, with loss of ethanol, giving an interesting fluorescent tetracyclic heteroaromatic compound. The antimicrobial activity, the minimal inhibitory concentrations (MICs) and the structure-activity relationships (SARs) were evaluated. A selectivity with low MICs was observed against Bacillus Cereus, and good results were also obtained against Candida albicans. The acids obtained by hydrolysis of the ester group, as non-proteinogenic α,β-unsaturated β-amino acids, can be incorporated into peptide chains to induce conformational constraints. |
publishDate |
2004 |
dc.date.none.fl_str_mv |
2004 2004-01-01T00:00:00Z 2008-09-12T13:25:40Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10198/820 |
url |
http://hdl.handle.net/10198/820 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Queiroz, Maria João R.P.; Begouin, Agathe; Ferreira, Isabel C.F.R.; Kirsch, Gilbert; Calhelha, Ricardo C.; Barbosa, Sandra; Estevinho, Leticia M. (2004). Palladium-catalysed amination of electron-deficient or relatively electron-rich benzo[b]thienyl bromides - Preliminary studies of antimicrobial activity and SARs. European Journal of Organic Chemistry. ISSN 1434-193X. 2004:4, p. 3679-3685 1434-193X 10.1002/ejoc.200400218 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Wiley Intersicence |
publisher.none.fl_str_mv |
Wiley Intersicence |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
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RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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