Synthesis and biological activity of simplified denoviose-coumarins related to novobiocin as potent inhibitors of heat-shock protein 90 (hsp90)

Bioorg Med Chem Lett. 2008 Apr 1;18(7):2495-8. doi: 10.1016/j.bmcl.2008.01.128. Epub 2008 Feb 14.

Abstract

A new series of coumarin inhibitors of hsp90 lacking the noviose moiety as well as substituents on C-7 and C-8 positions of the aromatic ring was synthesised and their hsp90 inhibitory activity has been delineated: for example, their capacity to induce the degradation of client proteins and to inhibit estradiol-induced transcription in human breast cancer cells. In cell proliferation assay, the most active compound 5g was approximately 8 times more potent than the parent novobiocin natural compound.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antibiotics, Antineoplastic / chemical synthesis
  • Antibiotics, Antineoplastic / pharmacology*
  • Binding Sites
  • Breast Neoplasms / pathology
  • Cell Line, Tumor / drug effects
  • Cell Proliferation / drug effects*
  • Coumarins / chemistry
  • Coumarins / pharmacology*
  • Drug Screening Assays, Antitumor
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology*
  • Estradiol / pharmacology
  • HSP90 Heat-Shock Proteins / antagonists & inhibitors*
  • Humans
  • Novobiocin / chemical synthesis
  • Novobiocin / pharmacology*
  • Structure-Activity Relationship
  • Transcription, Genetic / drug effects

Substances

  • Antibiotics, Antineoplastic
  • Coumarins
  • Enzyme Inhibitors
  • HSP90 Heat-Shock Proteins
  • Novobiocin
  • Estradiol