Design and synthesis of a series of piperazine-1-carboxamidine derivatives with antifungal activity resulting from accumulation of endogenous reactive oxygen species

ChemMedChem. 2009 Oct;4(10):1714-21. doi: 10.1002/cmdc.200900249.

Abstract

In this study, we screened a library of 500 compounds for fungicidal activity via induction of endogenous reactive oxygen species (ROS) accumulation. Structure-activity relationship studies showed that piperazine-1-carboxamidine analogues with large atoms or large side chains substituted on the phenyl group at the R(3) and R(5) positions are characterized by a high ROS accumulation capacity in Candida albicans and a high fungicidal activity. Moreover, we could link the fungicidal mode of action of the piperazine-1-carboxamidine derivatives to the accumulation of endogenous ROS.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry*
  • Antifungal Agents / pharmacology*
  • Candida albicans / drug effects*
  • Candida albicans / metabolism
  • Drug Design
  • Piperazines / chemical synthesis
  • Piperazines / pharmacology*
  • Reactive Oxygen Species / metabolism*
  • Structure-Activity Relationship

Substances

  • Antifungal Agents
  • Piperazines
  • Reactive Oxygen Species