Three 5H-indeno[1,2-c]pyridazin-5-one derivatives, potent type-B monoamine oxidase inhibitors

Acta Crystallogr C. 2004 Sep;60(Pt 9):o623-6. doi: 10.1107/S0108270104014660. Epub 2004 Aug 11.

Abstract

The structures of three compounds, namely 7-methoxy-2-[3-(trifluoromethyl)phenyl]-9H-indeno[1,2-c]pyridazin-9-one, C19H11F3N2O2, (Id), 6-methoxy-2-[3-(trifluoromethyl)phenyl]-9H-indeno[1,2-c]pyridazin-9-one, C19H11F3N2O2, (IId), and 2-methyl-6-(4,4,4-trifluorobutoxy)-9H-indeno[1,2-c]pyridazin-9-one, C16H13F3N2O2, (IIf), which are potent reversible type-B monoamine oxidase (MAO-B) inhibitors, are presented and discussed. Compounds (Id) and (IId) crystallize in a nearly planar conformation. The crystal structures are stabilized by weak C-H...O hydrogen bonds. The packing is dominated by pi-pi stacking interactions between the heterocyclic central moieties of centrosymmetrically related molecules. In compound (IIf), the trifluoroethyl termination is almost perpendicular to the plane of the ring.

MeSH terms

  • Crystallography, X-Ray
  • Heterocyclic Compounds, 3-Ring / chemistry*
  • Hydrogen Bonding
  • Indenes / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Monoamine Oxidase Inhibitors / chemistry*
  • Pyridazines / chemistry*

Substances

  • Heterocyclic Compounds, 3-Ring
  • Indenes
  • Monoamine Oxidase Inhibitors
  • Pyridazines