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

Eur J Med Chem. 2010 Dec;45(12):5732-8. doi: 10.1016/j.ejmech.2010.09.030. Epub 2010 Sep 17.


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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Catalysis
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Palladium / chemistry
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Pyridines / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tumor Cells, Cultured


  • Antineoplastic Agents
  • Pyridines
  • thienopyridine
  • Palladium