title: Synthesis of acyclovir and HBG analogues having nicotinonitrile and its 2-methyloxy 1,2,3-triazole.
abstract: 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.
authors.affiliation: Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt. ah_hu_mostafa@yahoo.com
authors.forename: Ahmed H
authors.initials: AH
authors.lastname: Moustafa
authors.forename: Hassan A
authors.initials: HA
authors.lastname: El-Sayed
authors.forename: Abd El-Fattah Z
authors.initials: Ael-F
authors.lastname: Haikal
authors.forename: El Sayed H
authors.initials: el SH
authors.lastname: El Ashry
mesh_terms: D000212:Acyclovir / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006147:Guanine / Q000031:analogs & derivatives*; D009539:Nicotinic Acids / Q000737:chemistry; D009570:Nitriles / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D009539:Nicotinic Acids; D009570:Nitriles; D014230:Triazoles; D006147:Guanine; D000212:Acyclovir