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Synthesis and antioxidant activity evaluation of new 7-aryl or 7-heteroarylamino-2,3-dimethylbenzo[b]thiophenes obtained by Buchwald–Hartwig C–N cross-coupling

2007Journal article Open access
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dc.contributor.authorQueiroz, Maria João R.P.
dc.contributor.authorFerreira, Isabel C.F.R.
dc.contributor.authorCalhelha, Ricardo C.
dc.contributor.authorEstevinho, Leticia M.
dc.date.accessioned2008-09-12T16:11:11Z
dc.date.available2008-09-12T16:11:11Z
dc.date.issued2007
dc.description.abstractNew 7-aryl or 7-heteroarylamino-2,3-dimethylbenzo[b]thiophenes were prepared by palladium-catalyzed Buchwald–Hartwig cross-coupling of 7-bromo or 7-amino-2,3-dimethylbenzo[b]thiophenes, previously prepared by us, with substituted (4-methoxy or 3,4-dimethoxy) anilines and 3-aminopyridine or with substituted (3-methoxy or 4-cyano) bromobenzenes and 2-bromopyridine, respectively, using Pd(OAc)2, rac-BINAP or Xantphos as ligands, and Cs2CO3 as base. Their antioxidant properties were evaluated by several methods: reducing power, scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals, inhibition of erythrocyte hemolysis and inhibition of lipid peroxidation using the b-carotene linoleate system. EC50 values for all the methods were determined and it was possible to establish some structure–activity relationships (SARs) based on the presence and position of different substituents on the phenyl ring (1 or 2 OMe and C„N), on the presence of a pyridine ring and on the position of its nitrogen atom relative to the N–H bond.en
dc.identifier.citationQueiroz, Maria João R.P.; Ferreira, Isabel C.F.R.; Calhelha, Ricardo C.; Estevinho, Leticia M. (2007). Synthesis and antioxidant activity evaluation of new 7-aryl or 7-heteroarylamino-2,3-dimethylbenzo[b]thiophenes obtained by Buchwald–Hartwig C–N cross-coupling. Bioorganic & Medicinal Chemistry. ISSN 0968-0896. 15:4, p. 1788-1794en
dc.identifier.doi10.1016/j.bmc.2006.11.035
dc.identifier.issn0968-0896
dc.identifier.urihttp://hdl.handle.net/10198/839
dc.language.isoengen
dc.publisherElsevieren
dc.subjectDiarylaminesen
dc.subjectBenzo[b]thiophenesen
dc.subjectBuchwald–Hartwig couplingen
dc.subjectAntioxidant activityen
dc.titleSynthesis and antioxidant activity evaluation of new 7-aryl or 7-heteroarylamino-2,3-dimethylbenzo[b]thiophenes obtained by Buchwald–Hartwig C–N cross-couplingen
dc.typejournal article
dspace.entity.typePublication
person.familyNameFerreira
person.familyNameCalhelha
person.familyNameMiranda Fernandes Estevinho
person.givenNameIsabel C.F.R.
person.givenNameRicardo C.
person.givenNameMaria Leticia
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
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