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Reaction of pyridin-2(1H)-one 1 with 4-bromobutylacetate (2), (2-acetoxyethoxy)methyl bromide (3) gave the corresponding nicotinonitrile O-acyclonucleosides, 4 and 5, respectively. Deacetylation of 4 and 5 gave the corresponding deprotected acyclonucleosides 6 and 7, respectively. Treatment of pyridin-2(1H)-one 1 with 1,3-dichloropropan-2-ol (8), epichlorohydrin (10) and allyl bromide (12) gave the corresponding nicotinonitrile O-acyclonucleosides 9, 11, and 13, respectively. Furthermore, reaction of pyridin-2(1H)-one 1 with the propargyl bromide (14) gave the corresponding 2-O-propargyl derivative 15, which was reacted via [3+2] cycloaddition with 4-azidobutyl acetate (16) and [(2-acetoxyethoxy)methyl]azide (17) to give the corresponding 1,2,3-triazole derivatives 18 and 19, respectively. The structures of the new synthesized compounds were characterized by using IR, (1)H, (13)C NMR spectra, and microanalysis. Selected members of these compounds were screened for antibacterial activity.

Glycosylation of 2-pyridonesulfonamide 1a,b with glycosyl/galactosyl bromide gave the corresponding glycosides 2a,b, 3a,b, 6a,b, and 7a,b, respectively. Deacetylation of the resulting glycosides gave the corresponding glycosides 4a,b, 5a,b, 8a,b, and 9a,b, respectively, in good yields. Furthermore, reaction of 2-pyridonesulfonamide 1b with lactosyl bromide gave a mixture the corresponding N, O-lactosides 10 and 11, which were deacetylated to give the corresponding glycosides 12 and 13, respectively. The structures of the new synthesized compounds were characterized by using IR, 1H, 13C NMR spectra, and microanalysis. Selected members of these compounds were screened for antimicrobial activity.

Glycosylation of pyridinone (IV) under conventional or microwave‐assisted conditions affords the corresponding O‐glycosides instead of the N‐glycosides.

Compounds (Va) and (VIb) possess significant antibacterial activity while all of the tested compounds show antifungal activity.

2,3-Triazole. -A series of title compounds of type (III) and (V) are prepared. Compounds (IIIa), (IIIb), (V), and the deacetylated analogues of (IIId) and (IIIe) show significant antibacterial activities. -(MOUSTAFA*, A. H.; EL-SAYED, H. A.; HAIKAL, A. E.-F. Z.; EL ASHRY, E. S. H.; Nucleosides, Nucleotides Nucleic Acids 30 (2011) 5, 340-352, http://dx.