Structure activity relationship study of benzo[d]thiazol-2(3H)one based σ receptor ligands

Bioorg Med Chem Lett. 2013 Sep 1;23(17):5011-3. doi: 10.1016/j.bmcl.2013.06.032. Epub 2013 Jun 29.

Abstract

Herein we report the SAR study which involved structural modifications to the linker length, aryl substitution and alkylamine ring size of the benzo[d]thiazol-2(3H)one based sigma receptor (σ) ligands. Many compounds in this series displayed low nanomolar affinity for the σ receptor subtypes. In particular, 8a showed high affinity (σ-1 Ki = 4.5 nM) for σ-1 receptors and moderately high selectivity (483-fold) over σ-2 receptors.

Keywords: 96 Well; Benzothiazolone; Sigma receptors.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Benzothiazoles / chemistry*
  • Benzothiazoles / pharmacology*
  • Binding Sites
  • Brain / drug effects
  • Brain / metabolism
  • Ligands
  • Protein Binding
  • Rats
  • Receptors, sigma / metabolism*
  • Sigma-1 Receptor
  • Structure-Activity Relationship

Substances

  • Benzothiazoles
  • Ligands
  • Receptors, sigma
  • sigma-2 receptor