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

• Type: Article in International Scientific Journal
• Date: 2010

Authors

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

Journal

Title: European Journal of Medicinal Chemistry

Vol. 45 No. 7

Pages: 5732-5738

ISSN: 0223-5234

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 25 Citations

ISI Web of Science

Scopus - 28 Citations

Pubmed / Medline

Scientific classification

CORDIS: Health sciences > Pharmacological sciences > Pharmacy

FOS: Medical and Health sciences > Basic medicine

Other information

Authenticus ID: 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 7