SAR and QSAR study on 2-aminothiazole derivatives, modulators of transcriptional repression in Huntington's disease

Bioorg Med Chem. 2008 May 15;16(10):5695-703. doi: 10.1016/j.bmc.2008.03.067. Epub 2008 Mar 30.

Abstract

REST/NRSF is a multifunctional transcription factor that represses or silences many neuron-specific genes in both neural and non-neural cells by recruitment to its cognate RE1/NRSE regulatory sites. An increase in RE1/NRSE genomic binding is found in Huntington's disease (HD), resulting in the repression of REST/NRSF regulated gene transcription, among which BDNF, thus representing one of the possible detrimental effectors in HD. Three 2-aminothiazole derivatives were recently identified as potent modulators of the RE1/NRSE silencing activity through a cell-based gene reporter assay. In this study, the structure-activity relationships (SAR) of a library of commercially available 2-aminoisothiazoles diversely substituted at the amino group or at position 4 has been evaluated. A quantitative structure-activity relationship analysis performed using the Phase strategy yielded highly predictive 3D-QSAR pharmacophore model for in silico drug screening.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Gene Expression Regulation / drug effects
  • Gene Expression Regulation / genetics
  • Gene Library
  • Gene Silencing / drug effects
  • Huntington Disease / drug therapy
  • Huntington Disease / genetics*
  • Models, Molecular
  • Molecular Structure
  • Quantitative Structure-Activity Relationship
  • Repressor Proteins / drug effects
  • Repressor Proteins / genetics
  • Reproducibility of Results
  • Stereoisomerism
  • Structure-Activity Relationship
  • Thiazoles / chemistry*
  • Thiazoles / pharmacology
  • Thiazoles / therapeutic use
  • Transcription, Genetic / drug effects

Substances

  • RE1-silencing transcription factor
  • Repressor Proteins
  • Thiazoles
  • 2-aminothiazole