title: Synthesis and biological activity of some nucleoside analogs of hydroquinoline-3-carbonitrile.
abstract: Hydroquinoline acyclonucleosides 2, 4, 6a,b, 8a,b, 9a,b, and their corresponding N-alkyl derivatives (10-12) were obtained by the reaction of 1a,b with acetoxybutylbromide, (2-acetoxyethoxy)methyl bromide, 3-chloropropanol, 1,3-dichloro-2-propanol, epichlorohydrin, propargyl/allyl bromides in the presence of K(2)CO(3) in dry dimethylformamide (DMF). In a similar manner, reaction of 1a,b with glycosyl/galactosyl and lactosyl bromide afforded the corresponding N-nucloside derivatives 13a,b, 15a,b, and 17, respectively. Deacetylation of the N-nucleosides derivatives in the presence of Et(3)N/MeOH and few drops of water gave the deprotected derivatives 3, 5, 7a,b, 14a,b, 16a,b, and 18 in good yields, respectively. All the newly synthesized compounds are elucidated by infrared, (1)H, (13)C NMR and elemental analyses. Some of these compounds were screened for antimicrobial activities.
authors.affiliation: a Department of Chemistry, Faculty of Science , Zagazig University , Zagazig , Egypt.
authors.forename: Ahmed H
authors.initials: AH
authors.lastname: Moustafa
authors.forename: Said A
authors.initials: SA
authors.lastname: Said
authors.forename: Abd-El Fattah Z
authors.initials: AE
authors.lastname: Haikal
authors.forename: Rajab
authors.initials: R
authors.lastname: Abu-El-Halawa
authors.forename: Rimaa T
authors.initials: RT
authors.lastname: Abd-El Kader
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry*; D013055:Spectrophotometry, Infrared
chemical_list: D000900:Anti-Bacterial Agents; D009570:Nitriles; D009705:Nucleosides; D011804:Quinolines