N-long-chain monoacylated derivatives of 2,6-diaminopyridine with antiviral activity.
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.
Mibu
Nobuko
N
Pharmaceutical Sciences, Fukuoka University, Fukuoka 814-0180, Japan.
Yokomizo
Kazumi
K
Kashige
Nobuhiro
N
Miake
Fumio
F
Miyata
Takeshi
T
Uyeda
Masaru
M
Sumoto
Kunihiro
K
D000215:Acylation; D000818:Animals; D000998:Antiviral Agents / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D002522:Chlorocebus aethiops; D008826:Microbial Sensitivity Tests; D011725:Pyridines / Q000737:chemistry / Q000494:pharmacology*; D014709:Vero Cells
D000998:Antiviral Agents; D011725:Pyridines; C505797:2,6-diaminopyridine