Synthesis and antiproliferative activity of 2-chlorophenyl carboxamide thienopyridines

Bioorg Med Chem Lett. 2017 Jan 15;27(2):135-138. doi: 10.1016/j.bmcl.2016.12.009. Epub 2016 Dec 5.

Abstract

3-Amino-2-arylcarboxamide-thieno[2,3-b]pyridines are a known class of antiproliferative compounds with activity against the phospholipase C enzyme. To further investigate the structure activity relationships of these derivatives a series of analogues were prepared modifying key functional groups. It was determined that modification of the 3-amino and 2-aryl carboxamide functionalities resulted in complete elimination of activity, whilst modification at C-5 allowed compounds of greater activity to be prepared.

Keywords: Antiproliferative; Cancer; Phospholipase C; Thieno[2,3-b]pyridine; Tyrosyl-DNA phosphodiesterase I.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacology*
  • Binding Sites
  • Cell Line, Tumor
  • Humans
  • Hydrogen Bonding
  • Molecular Docking Simulation
  • Phospholipase C delta / antagonists & inhibitors
  • Phospholipase C delta / chemistry
  • Pyridines / chemical synthesis
  • Pyridines / pharmacology*
  • Quinolines / chemical synthesis
  • Quinolines / pharmacology*
  • Thiophenes / chemical synthesis
  • Thiophenes / pharmacology*

Substances

  • 3-amino-2-((2'-chlorophenyl)carbamoyl)-5,6,7,8-tetrahydrothieno(2,3-b)quinolin-5-yl acetate
  • Antineoplastic Agents
  • Pyridines
  • Quinolines
  • Thiophenes
  • PLCD1 protein, human
  • Phospholipase C delta