Synthesis and evaluation of tumor cell growth inhibition of Methyl 3-Amino-6-[(...

• Author(s): Queiroz, Maria João R. P. ; Calhelha, Ricardo C. ; Silva, Luís A. Vale ; Pinto, Eugénia ; Almeida, Gabriela M. ; Vasconcelos, M. Helena
• Date: 2011
• Persistent ID: http://hdl.handle.net/1822/14372
• Origin: RepositóriUM - Universidade do Minho
• Subject(s): Thieno[3,2-b]pyridines; Sonogashira coupling; Antitumoral activity; Cell Cycle; Apoptosis
• Document Type: Article
• Language: English

Description

The methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate, recently reported by some of us, was reacted in Sonogashira couplings with several (hetero)arylacetylenes. The growth inhibitory activity of the novel methyl 3-amino-6-[(hetero)arylethynyl]thieno[3,2-b]pyridine-2-carboxylates obtained was evaluated on three human tumor cell lines (MCF-7, NCI-H460, A375-C5). The para-methoxyphenyl and the ortho and para-aminophenyl derivatives were the most promising compounds, and their effects were further studied regarding alterations in the normal cell cycle distribution and induction of apoptosis in the NCI-H460 cell line. All three compounds altered cell cycle distribution and the ortho-aminophenyl derivative was further shown to induce apoptosis in the same cell line.