N-long-chain monoacylated derivatives of 2,6-diaminopyridine with antiviral activity.

Abstract

N-Monoacyl-2,6-diaminopyridines (2a-c) and N,N'-diacyl-2,6-diaminopyridines (3a-c) were synthesized from 2,6-diaminopyridine by acylation with the corresponding acyl halide or by dehydration with the corresponding carboxylic acid using 1,3-dicyclohexylcarbodiimide (DCC). The antiviral activities of N-monoacyl- and N,N'-diacyl-2,6-diaminopyridines (2a-c and 3a-c) were estimated using plaque reduction assay with HSV-1. All N-monoacyl derivatives (2a-c) showed significant anti-herpes simplex virus (HSV)-1 activity (EC(50) = 15.3-18.5 microg/ml). The CC(50) values of 2a-c measured using Vero cells ranged at 37.5-50.0 microg/ml. These compounds showed no significant antibacterial activities with Escherichia coli or Staphylococcus aureus even at a concentration of 1 mg/ml. The N,N'-diacyl derivatives (3a-c) showed no significant anti-HSV-1 activity.

• Authors: Nobuko Mibu, Kazumi Yokomizo, Nobuhiro Kashige, Fumio Miake, Takeshi Miyata, Masaru Uyeda, Kunihiro Sumoto
• Journal: Chemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 55 Issue 1 Pg. 111-4 (Jan 2007) ISSN: 0009-2363 [Print] Japan
• PMID: 17202712 (Publication Type: Journal Article)

Chemical References

• Antiviral Agents
• Pyridines
• 2,6-diaminopyridine

Topics

• Acylation
• Animals
• Antiviral Agents (chemistry, pharmacology)
• Cell Line
• Chlorocebus aethiops
• Microbial Sensitivity Tests
• Pyridines (chemistry, pharmacology)
• Vero Cells