Design and synthesis of fused tetrahydroisoquinoline-iminoimidazolines

Eur J Med Chem. 2015 Dec 1:106:15-25. doi: 10.1016/j.ejmech.2015.10.030. Epub 2015 Oct 19.

Abstract

In the aim of identifying new privileged structures, we describe the 5-steps synthesis of cyclic guanidine compounds "tetrahydroisoquinoline-iminoimidazolines" derived from tetrahydroisoquinoline-hydantoin core. In order to evaluate this new minimal structure and the impact of replacing a carbonyle by a guanidine moiety, their affinity towards adenosine receptor A2A was evaluated and compared to those of tetrahydroisoquinoline-hydantoin compounds.

Keywords: A(2A) receptor; Guanidines; Iminoimidazoline; Privileged structure.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Dose-Response Relationship, Drug
  • Drug Design*
  • HEK293 Cells
  • Humans
  • Imidazolines / chemical synthesis
  • Imidazolines / chemistry
  • Imidazolines / pharmacology*
  • Models, Molecular
  • Molecular Structure
  • Purinergic P1 Receptor Antagonists / chemical synthesis*
  • Purinergic P1 Receptor Antagonists / chemistry
  • Purinergic P1 Receptor Antagonists / pharmacology*
  • Receptor, Adenosine A2A / metabolism*
  • Structure-Activity Relationship
  • Tetrahydroisoquinolines / chemical synthesis
  • Tetrahydroisoquinolines / chemistry
  • Tetrahydroisoquinolines / pharmacology*

Substances

  • Imidazolines
  • Purinergic P1 Receptor Antagonists
  • Receptor, Adenosine A2A
  • Tetrahydroisoquinolines