Selective CB2 receptor agonists. Part 1: the identification of novel ligands through computer-aided drug design (CADD) approaches

Bioorg Med Chem Lett. 2015 Feb 1;25(3):575-80. doi: 10.1016/j.bmcl.2014.12.033. Epub 2014 Dec 17.

Abstract

Computer-aided drug design scaffold hopping strategies were utilized to identify new classes of CB2 agonists when compounds of an established series with low nanomolar potency were challenging to optimize for good drug-like properties. Use of ligand-based design strategies through BI Builder (a tool for de novo design) and PharmShape (a virtual screening software package) approaches led to the discovery of new chemotypes. Specifically, compounds containing azetidine-, proline-, and piperidine-based cores were found to have low nanomolar and picomolar CB2 agonist activities with drug-like properties considered appropriate for early profiling.

Keywords: Cannabinoid receptor 2; De-novo design; Ligand-based; Proline; Scaffold hopping.

MeSH terms

  • Computer-Aided Design
  • Drug Design*
  • Humans
  • Ligands
  • Microsomes, Liver / metabolism
  • Protein Binding
  • Receptor, Cannabinoid, CB1 / agonists
  • Receptor, Cannabinoid, CB1 / metabolism
  • Receptor, Cannabinoid, CB2 / agonists*
  • Receptor, Cannabinoid, CB2 / metabolism
  • Solubility
  • Structure-Activity Relationship

Substances

  • Ligands
  • Receptor, Cannabinoid, CB1
  • Receptor, Cannabinoid, CB2