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Synthesis, biological evaluation, and pharmacophore generation of uracil, 4(3H)-pyrimidinone, and uridine derivatives as potent and selective inhibitors of parainfluenza 1 (Sendai) virus.

Abstract
Several new 6-oxiranyl-, 6-oxiranylmethyluracils, and pyrimidinone derivatives, synthesized by lithiation-alkylation sequence of 1,3,6-trimethyluracil, 1,3-dimethyl-6-chloromethyluracil, and 2-alkoxy-6-methyl-4(3H)-pyrimidinones, showed a potent and selective antiviral activity against Sendai virus (SV) replication. To gain insight into the structural features required for SV inhibition activity, the new compounds were submitted to a pharmacophore generation procedure using the program Catalyst. The resulting pharmacophore model showed high correlation and predictive power. It also rationalized the relationships between structural properties and biological data of these inhibitors of SV replication.
AuthorsR Saladino, C Crestini, A T Palamara, M C Danti, F Manetti, F Corelli, E Garaci, M Botta
JournalJournal of medicinal chemistry (J Med Chem) Vol. 44 Issue 26 Pg. 4554-62 (Dec 20 2001) ISSN: 0022-2623 [Print] United States
PMID11741474 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Antiviral Agents
  • Pyrimidinones
  • Uracil
  • Uridine
Topics
  • Animals
  • Antiviral Agents (chemical synthesis, chemistry, pharmacology)
  • Cell Line
  • Dogs
  • Models, Molecular
  • Molecular Conformation
  • Pyrimidinones (chemical synthesis, chemistry, pharmacology)
  • Sendai virus (drug effects)
  • Stereoisomerism
  • Structure-Activity Relationship
  • Uracil (analogs & derivatives, chemical synthesis, chemistry, pharmacology)
  • Uridine (analogs & derivatives, chemical synthesis, chemistry, pharmacology)

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