Precursor of a beta-lactamase inhibitor: allyl (4S,8S,9R)-10-[(E)-ethylidene]-4-methoxy-11-oxo-1-azatricyclo[7.2.0.0(3,8)]undec-2-ene-2-carboxylate

Acta Crystallogr C. 2002 Jun;58(Pt 6):o367-9. doi: 10.1107/s010827010200793x. Epub 2002 May 31.

Abstract

The molecular structure of the title tricyclic compound, C(17)H(21)NO(4), which is the immediate precursor of a potent synthetic inhibitor [Lek157: sodium (8S,9R)-10-[(E)-ethylidene]-4-methoxy-11-oxo-1-azatricyclo[7.2.0.0(3,8)]undec-2-ene-2-carboxylate] with remarkable potency, provides experimental evidence for the previously modelled relative position of the fused cyclohexyl ring and the carbonyl group of the beta-lactam ring, which takes part in the formation of the initial tetrahedral acyl-enzyme complex. In this hydrophobic molecule, the overall geometry is influenced by C[bond]H...O intramolecular hydrogen bonds [3.046 (4) and 3.538 (6) A, with corresponding normalized H.O distances of 2.30 and 2.46 A], whereas the molecules are interconnected through intermolecular C[bond]H...O hydrogen bonds [3.335 (4)-3.575 (5) A].

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aza Compounds / chemistry*
  • Crystallography, X-Ray
  • Enzyme Inhibitors / chemistry*
  • Heterocyclic Compounds, 3-Ring / chemistry*
  • Models, Molecular
  • Molecular Structure
  • beta-Lactamase Inhibitors*

Substances

  • Aza Compounds
  • Enzyme Inhibitors
  • Heterocyclic Compounds, 3-Ring
  • allyl-(4,8,9)-10-(ethylidene)-4-methoxy-11-oxo-1-azatricyclo(7.2.0.0(3,8))undec-2-ene-2-carboxylate
  • beta-Lactamase Inhibitors