Discovery of N-aryl-naphthylamines as in vitro inhibitors of the interaction between HIV integrase and the cofactor LEDGF/p75

Eur J Med Chem. 2015 Aug 28:101:288-94. doi: 10.1016/j.ejmech.2015.06.036. Epub 2015 Jun 22.

Abstract

A series of N-aryl-naphthylamines, exemplified by the structures 11-16, were chosen for an in-house library screening to assay their ability to disrupt the interaction between the LEDGF cofactor and the HIV integrase. Structure modification led also to design and synthesize new compounds 17a-f. Compounds 11e,h,k,n, 13b, and 14 showed good activity in AlphaScreen assay. The most active compound 11e (IC50 = 2.5 μM) was selected for molecular modeling studies and showed a binding mode similar to the one of the known LEDGIN 8.

Keywords: Integrase; LEDGF/p75; LEDGINs; N-aryl-naphthylamine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1-Naphthylamine / analogs & derivatives*
  • 1-Naphthylamine / chemical synthesis
  • 1-Naphthylamine / chemistry
  • 1-Naphthylamine / pharmacology
  • Dose-Response Relationship, Drug
  • Drug Discovery*
  • HIV Integrase / metabolism*
  • HIV Integrase Inhibitors / chemical synthesis
  • HIV Integrase Inhibitors / chemistry
  • HIV Integrase Inhibitors / pharmacology*
  • Humans
  • Intercellular Signaling Peptides and Proteins / metabolism*
  • Models, Molecular
  • Molecular Structure
  • Protein Binding / drug effects
  • Structure-Activity Relationship
  • Tumor Cells, Cultured
  • para-Aminobenzoates / chemical synthesis
  • para-Aminobenzoates / chemistry
  • para-Aminobenzoates / pharmacology*

Substances

  • HIV Integrase Inhibitors
  • Intercellular Signaling Peptides and Proteins
  • lens epithelium-derived growth factor
  • para-Aminobenzoates
  • 1-Naphthylamine
  • HIV Integrase