The furan route to tropolones: probing the antiproliferative effects of β-thujaplicin analogs

Org Biomol Chem. 2012 Nov 21;10(43):8597-604. doi: 10.1039/c2ob26553b.

Abstract

A direct route to analogs of the naturally occurring tropolone β-thujaplicin has been developed in just four steps from furan. Using this method, a series of derivatives were synthesized and evaluated. Several of these compounds demonstrated very high levels of potency against bacterial and fungal pathogens with good selectivity over mammalian cells.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Candida glabrata / drug effects
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Enterococcus faecalis / drug effects
  • Furans / chemistry*
  • Humans
  • MCF-7 Cells
  • Molecular Structure
  • Monoterpenes / chemical synthesis
  • Monoterpenes / chemistry
  • Monoterpenes / pharmacology*
  • Staphylococcus aureus / drug effects
  • Structure-Activity Relationship
  • Tropolone / analogs & derivatives*
  • Tropolone / chemical synthesis
  • Tropolone / chemistry
  • Tropolone / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Antineoplastic Agents
  • Furans
  • Monoterpenes
  • Tropolone
  • beta-thujaplicin
  • furan