Synthesis and cytotoxicity of thieno[2,3-b]quinoline-2-carboxamide and cycloalkyl[b]thieno[3,2-e]pyridine-2-carboxamide derivatives

Bioorg Med Chem. 2016 Mar 1;24(5):1142-54. doi: 10.1016/j.bmc.2016.01.047. Epub 2016 Jan 27.

Abstract

Seventy nine derivatives of thieno[2,3-b]quinolines, tetrahydrothieno[2,3-b]quinoline, dihydrocyclopenta[b]thieno[3,2-e]pyridine, cyclohepta[b]thieno[3,2-e]pyridine and hexahydrocycloocta[b]thieno[3,2-e]pyridine were either synthesized or obtained commercially and tested for their antiproliferative activity against HCT116, MDA-MB-468 and MDA-MB-231 human cancer cell lines. The most potent eight compounds were active against all cell lines with IC50 values in the 80-250nM range. In general hexahydrocycloocta[b]thieno[3,2-e]pyridines were most active with increasing activity observed as larger cycloalkyl rings were fused to the pyridine ring.

Keywords: Antiproliferative; Thieno[2,3-b]pyridines; Thieno[2,3-b]quinolones; Thieno[3,2-e]pyridines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects*
  • Drug Screening Assays, Antitumor
  • Humans
  • Neoplasms / drug therapy
  • Quinolines / chemical synthesis
  • Quinolines / chemistry*
  • Quinolines / pharmacology*
  • Structure-Activity Relationship
  • Thienopyridines / chemical synthesis
  • Thienopyridines / chemistry*
  • Thienopyridines / pharmacology*

Substances

  • Antineoplastic Agents
  • Quinolines
  • Thienopyridines
  • quinoline-3-carboxamide