3-Nitro-2H-chromenes as a new class of inhibitors against thioredoxin reductase and proliferation of cancer cells

Arch Pharm (Weinheim). 2012 Oct;345(10):767-70. doi: 10.1002/ardp.201200121. Epub 2012 Jul 26.

Abstract

A series of 3-nitrochromenes were designed and synthesized. These compounds showed good inhibitory activity against thioredoxin reductase (TrxR) and the proliferation of A549 cancer cells. The structure-activity relationship analysis indicates that the 3-nitrochromene scaffold is the crucial pharmacophore for achieving good inhibitory activity. The bromo-substitutions at the 6- and 8-position of 3-nitrochromene significantly increase the inhibitory activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzopyrans / chemical synthesis
  • Benzopyrans / chemistry
  • Benzopyrans / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Nitro Compounds / chemical synthesis
  • Nitro Compounds / chemistry
  • Nitro Compounds / pharmacology*
  • Structure-Activity Relationship
  • Thioredoxin-Disulfide Reductase / antagonists & inhibitors*

Substances

  • Benzopyrans
  • Enzyme Inhibitors
  • Nitro Compounds
  • Thioredoxin-Disulfide Reductase