Please use this identifier to cite or link to this item: http://hdl.handle.net/10198/839
Title: 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
Authors: Queiroz, Maria João R.P.
Ferreira, Isabel C.F.R.
Calhelha, Ricardo C.
Estevinho, Leticia M.
Keywords: Diarylamines
Benzo[b]thiophenes
Buchwald–Hartwig coupling
Antioxidant activity
Issue Date: 2007
Publisher: Elsevier
Citation: Queiroz, 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. 1788-1794
Abstract: New 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.
URI: http://hdl.handle.net/10198/839
ISSN: 0968-0896
Appears in Collections:BB - Artigos em Revistas Indexados ao ISI/Scopus

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