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Palladium-catalysed amination of electron-deficient or relatively electron-rich benzo[b]thienyl bromides - Preliminary studies of antimicrobial activity and SARs

2004Journal article Open access
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dc.contributor.authorQueiroz, Maria João R.P.
dc.contributor.authorBegouin, Agathe
dc.contributor.authorFerreira, Isabel C.F.R.
dc.contributor.authorKirsch, Gilbert
dc.contributor.authorCalhelha, Ricardo C.
dc.contributor.authorBarbosa, Sandra
dc.contributor.authorEstevinho, Leticia M.
dc.date.accessioned2008-09-12T13:25:40Z
dc.date.available2008-09-12T13:25:40Z
dc.date.issued2004
dc.description.abstractSeveral 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.en
dc.identifier.citationQueiroz, 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. 3679-3685en
dc.identifier.doi10.1002/ejoc.200400218
dc.identifier.issn1434-193X
dc.identifier.urihttp://hdl.handle.net/10198/820
dc.language.isoengen
dc.publisherWiley Intersicenceen
dc.subjectAminationen
dc.subjectAntimicrobial activityen
dc.subjectBenzothiophenesen
dc.subjectDiarylaminesen
dc.subjectFluorescenceen
dc.subjectPalladiumen
dc.titlePalladium-catalysed amination of electron-deficient or relatively electron-rich benzo[b]thienyl bromides - Preliminary studies of antimicrobial activity and SARsen
dc.typejournal article
dspace.entity.typePublication
person.familyNameFerreira
person.familyNameCalhelha
person.familyNameEstevinho
person.givenNameIsabel C.F.R.
person.givenNameRicardo C.
person.givenNameLetícia M.
person.identifier144781
person.identifier.ciencia-id9418-CF95-9919
person.identifier.ciencia-idF313-E3CE-554E
person.identifier.ciencia-idBA14-09D6-A406
person.identifier.orcid0000-0003-4910-4882
person.identifier.orcid0000-0002-6801-4578
person.identifier.orcid0000-0002-9249-1948
person.identifier.ridE-8500-2013
person.identifier.ridJ-2172-2014
person.identifier.scopus-author-id36868826600
person.identifier.scopus-author-id6507978333
person.identifier.scopus-author-id6506577664
rcaap.rightsopenAccess
rcaap.typearticleen
relation.isAuthorOfPublicationbd0d1537-2e03-41fb-b27a-140af9c35db8
relation.isAuthorOfPublication2d5d1a41-7561-4a01-871c-b4c97da35053
relation.isAuthorOfPublication4a1d5ba2-1854-4ca5-89a4-73f35e964df9
relation.isAuthorOfPublication.latestForDiscovery2d5d1a41-7561-4a01-871c-b4c97da35053

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