Novel 6-[(hetero)arylamino]thieno[3,2-b]pyridines: Synthesis and antitumoral activities

• Tipo: Artigo em Revista Científica Internacional
• Data: 2010

Autores

Maria Joao R P Queiroz (Autor) Outra; Ricardo C Calhelha (Autor) Outra; Luis A Vale Silva (Autor) Outra; Eugenia Pinto (Autor) FFUP; Sao Jose Nascimento, MSJ (Autor) FFUP

Revista

Título: European Journal of Medicinal Chemistry

Vol. 45 Nº 7

Páginas: 5732-5738

ISSN: 0223-5234

Editora: Elsevier

Indexação

ISI Web of Knowledge - 25 Citações

ISI Web of Science

Scopus - 28 Citações

Pubmed / Medline

Classificação Científica

CORDIS: Ciências da Saúde > Ciências farmacológicas > Farmácia

FOS: Ciências médicas e da saúde > Medicina básica

Outras Informações

ID Authenticus: P-003-0F9

DOI: 10.1016/j.ejmech.2010.09.030

Resumo (PT): Several novel 6-[(hetero)arylamino]thieno[3,2-b]pyridines were prepared by palladium-catalyzed C–N Buchwald–Hartwig coupling of the methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate with aryl and heteroarylamines, using different reaction conditions. The antitumoral activity of the di(hetero)arylamines obtained was evaluated against three representative human tumor cell lines, namely breast adenocarcinoma (MCF-7), melanoma (A375-C5), and non-small cell lung cancer (NCI-H460) and some structure–activity relationships were established within each series. The most promising compounds were shown to be a benzothiazole derivative with GI50 3.5–6.9 μM followed by an indole derivative with GI50 13–21 μM. <br> <br> Keywords: Di(hetero)arylamines; Thieno[3,2-b]pyridines; Palladium; Buchwald–Hartwig coupling; Antitumor activity; SARs <br> <a target="_blank" href="http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6VKY-511TN6F-5&_user=2460038&_coverDate=12%2F31%2F2010&_rdoc=25&_fmt=high&_orig=browse&_origin=browse&_zone=rslt_list_item&_srch=doc-info(%23toc%236135%232010%23999549987%232662735%23FLA%23display%23Volume)&_cdi=6135&_sort=d&_docanchor=&view=c&_ct=79&_acct=C000057398&_version=1&_urlVersion=0&_userid=2460038&md5=f2581d53eefbd682d78fc94143870fe3&searchtype=a "> Texto integral </a> <br> <br>

Abstract (EN): Several novel 6-[(hetero)arylamino]thieno[3,2-b]pyridines were prepared by palladium-catalyzed C-N Buchwald-Hartwig coupling of the methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate with aryl and heteroarylamines, using different reaction conditions. The antitumoral activity of the di(hetero) arylamines obtained was evaluated against three representative human tumor cell lines, namely breast adenocarcinoma (MCF-7), melanoma (A375-05), and non-small cell lung cancer (NCI-H460) and some structure activity relationships were established within each series. The most promising compounds were shown to be a benzothiazole derivative with GI(50) 3.5-6.9 mu M followed by an indole derivative with GI(50) 13-21 mu M.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 7