3-Substituted-(5-arylfuran-2-ylcarbonyl)guanidines as NHE-1 inhibitors

Bioorg Med Chem Lett. 2007 Mar 1;17(5):1291-5. doi: 10.1016/j.bmcl.2006.12.012. Epub 2006 Dec 15.

Abstract

The C-3 substituents effect on NHE-1 inhibitory activity of (5-arylfuran-2-ylcarbonyl)guanidines, previously identified as potent NHE-1 inhibitors, was investigated. The introduction of amine or alkyl groups at the 3-position of the furan ring, next to the acylguanidine moiety, remarkably improves NHE-1 inhibitory potency. Especially the important finding is that 5-(2,5-dichloro)phenyl and 5-(2-methoxy-5-chloro)phenyl derivatives exhibit high NHE-1 inhibitory activities (IC50 < 0.02 microM) that match those of 3-unsubstituted derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cardiotonic Agents / chemical synthesis
  • Guanidine / analogs & derivatives
  • Guanidine / chemical synthesis*
  • Guanidine / pharmacology*
  • Heart / drug effects
  • Heart / physiopathology
  • In Vitro Techniques
  • Inhibitory Concentration 50
  • Myocardial Ischemia / drug therapy
  • Myocardial Reperfusion Injury / drug therapy
  • Rats
  • Sodium-Hydrogen Exchangers / antagonists & inhibitors*
  • Structure-Activity Relationship

Substances

  • Cardiotonic Agents
  • Sodium-Hydrogen Exchangers
  • growth factor-activatable Na-H exchanger NHE-1
  • Guanidine