Two stereoisomers of the rat toxicant norbormide

Acta Crystallogr C. 2004 May;60(Pt 5):o374-6. doi: 10.1107/S0108270104006845. Epub 2004 Apr 30.

Abstract

The structures of two diastereoisomers of norbormide [systematic name: 5-[hydroxy(phenyl)(2-pyridyl)methyl]-8-[phenyl(2-pyridyl)methylene]-3a,4,7,7a-tetrahydro-4,7-methano-1H-isoindole-1,3(2H)-dione], viz. the unsolvated molecule, C(33)H(25)N(3)O(3), and the ethyl acetate hemisolvate, C(33)H(25)N(3)O(3).0.5C(4)H(8)O(2), have been determined unambiguously. They differ in the relative stereochemistry about the exocyclic double bond and the relative conformations of the aryl rings. Each compound exhibits both intra- and intermolecular hydrogen bonding.

MeSH terms

  • Animals
  • Hydrogen Bonding
  • Models, Chemical
  • Norbornanes / chemical synthesis
  • Norbornanes / chemistry*
  • Norbornanes / toxicity
  • Rats
  • Stereoisomerism

Substances

  • Norbornanes
  • norbormide