Biblioteca Digital do Instituto Politécnico de Bragança   Instituto Politécnico de Bragança

Biblioteca Digital do IPB >
Escola Superior Agrária >
Biologia e Biotecnologia >
BB - Artigos em Revistas Indexados ao ISI >

Please use this identifier to cite or link to this item: http://hdl.handle.net/10198/820

Título: Palladium-catalysed amination of electron-deficient or relatively electron-rich benzo[b]thienyl bromides: preliminary studies of antimicrobial activity and SARs
Autor: Queiroz, Maria João R.P.
Begouin, Agathe
Ferreira, Isabel C.F.R.
Kirsch, Gilbert
Calhelha, Ricardo C.
Barbosa, Sandra
Estevinho, Leticia M.
Palavras-chave: Amination
Antimicrobial activity
Benzothiophenes
Diarylamines
Fluorescence
Palladium
Issue Date: 2004
Editora: Wiley Intersicence
Citação: European Journal of Organic Chemistry. ISSN 1434-193X. 2004:4 (2004) p. 3679-3685
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.
URI: http://hdl.handle.net/10198/820
ISSN: 1434-193X
Appears in Collections:BB - Artigos em Revistas Indexados ao ISI

Files in This Item:

File Description SizeFormat
2004EJOC.PDF146,92 kBAdobe PDFView/Open
Statistics
FacebookTwitterDeliciousLinkedInDiggGoogle BookmarksMySpaceOrkut
Formato BibTex mendeley Endnote Logotipo do DeGóis 

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

 


  © Instituto Politécnico de Bragança - Biblioteca Digital - Feedback - Statistics
  Estamos no RCAAP Governo Português separator Ministério da Educação e Ciência   Fundação para a Ciência e a Tecnologia

Financiado por:

POS_C UE