Two related potent antiviral compounds: 3-bromo-N-butyl-4-butylamino-1,8-naphthalenedicarboximide (1) and 4-amino-3-bromo-N-butyl-1,8-naphthalenedicarboximide (2)

Acta Crystallogr C. 1995 Jun 15:51 ( Pt 6):1189-93. doi: 10.1107/s0108270194011005.

Abstract

The crystal structures of two brominated derivatives of 4-amino-N-butyl-1,8-naphthalenedicarboximide [alternative systematic names: 8-bromo-2-butyl-7-butylamino-1H-benzo[de]isoquinoline-1,3(2H)-dione, C20H23BrN2O2, and 7-amino-8-bromo-2-butyl-1H-benzo[de]isoquinoline-1,3(2H)-dione, C16H15BrN2O2] are reported. The N-butyl groups, which are common to both compounds, are perpendicular to the plane of the naphthalenedicarboximide ring system. The butylamino group at position 4 in (1) is in the plane of the naphthalenedicarboximide ring, with the butyl group oriented towards the peri position of the naphthalenedicarboximide ring. This arrangement results in an opening of the (ring C)-N-(butyl C) angle.

MeSH terms

  • Antiviral Agents / chemistry*
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Naphthalenes / chemistry*

Substances

  • 3-bromo-N-butyl-4-butylamino-1,8-naphthalendicarboximide
  • 4-amino-3-bromo-N-butyl-1,8-naphthalenedicarboximide
  • Antiviral Agents
  • Naphthalenes