[The structure and antiviral activity of ribavirin analogs. II. Molecular and crystal structure of 1-(1,5-dihydroxy-3-oxapent-2-yl)-1,2,4-triazole-5-carboxamide]

Bioorg Khim. 1988 Aug;14(8):1092-7.
[Article in Russian]

Abstract

X-ray structure of the title compound, an antiviral agent moderately active towards Herpes simplex virus type 1, has been determined. The space group is P2i/n, unit cell parameters: a = 10,119, b = 7,529, c = 13,585 A, beta = 107,82 degrees, Z = 4. The structure was solved by the direct method and refined by least-squares procedure to R = 2.9%. The gauche-conformation about C4'-C5' bond and trans-conformation about O4'-C4' bond are realized in the molecule. The carboxyamide group at the C5 atom of triazol cycle provides a steric opportunity for the intramolecular hydrogen bond C1'-H1'...O6 formation.

Publication types

  • English Abstract

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Chemical Phenomena
  • Chemistry
  • Crystallization
  • Models, Molecular
  • Molecular Conformation
  • Ribavirin / analogs & derivatives
  • Ribavirin / chemical synthesis
  • Simplexvirus / drug effects
  • Triazoles / chemical synthesis*
  • Triazoles / pharmacology

Substances

  • Antiviral Agents
  • Triazoles
  • 1-(1,5-dihydroxy-3-oxapent-2-yl)-1,2,4-triazole-5-carboxamide
  • Ribavirin