Synthesis and antibacterial activity of some glucosyl- and ribosyl-pyridazin-3-ones.
Reaction of 5,6-diphenylpyridazin-3(2H)-one 1a,b with 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl bromide 2 in K(2)CO(3)/acetone gave 5,6-diphenyl-N(2)-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyl)pyridazin-3-one 5a,b. The same nucleosides 5a,b were obtained by reaction of 1a,b with peracetylated glucose 3 under MW irradiation. Mercuration of 1a,b followed by reaction with glucosyl bromide 2 gave the same nucleosides 5a,b. The riboside 4-cyano-5,6-diphenyl-N(2)-(2',3',5'-tri-O-acetyl-beta-D-ribofuranosyl)-pyridazin-3-one 8 was obtained by reaction of 4-cyanopyridazinone 1b with peracetylated ribose 7 under MW irradiation. The deprotected nucleosides 6a,b and 9 were obtained by stirring of 5a,b and 8 in methanol and TEA/H(2)O. The structure was confirmed using (1)H and (13)C-NMR spectra. Selected members of these compounds were screened for antibacterial activity.
El-Sayed
H A
HA
Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt.
Moustafa
A H
AH
Haikal
A Z
AZ
El-Ashry
E S H
ES