title: Homoacyclovir analogues of unnatural bases and their activity against hepatitis B virus.
abstract: The ambident nucleophilic nature of the sodium salts of 2(1H)-qunioxalinone (2) and the phthalazinedione (3) has been realized from their alkylation with 2-(2-chloroethoxy)ethylacetate (1) to afford 1-[2-(2-acetoxyethoxy)ethyl]-2(1H)-quinoxalinone (8) and 2-[2-(2-acetoxyethoxy)ethoxy]qunioxaline (9) as well as 10 and 11, respectively. The corresponding derivatives 12-15 were similarly prepared by the alkylation of the unnatural bases 4-7 with 1. Treatment of the alkylated derivatives 8-15 with methanolic ammonia solution (1:1) at room temperature gave the corresponding hydroxyalkyl derivatives 16-23. The site of the alkylation was deduced from the spectral characteristics of the products. The activity of compounds 16-22 against Hepatitis B virus (HBV) in HepG2 cell has been tested. Some of the compounds showed high viral replication inhibition with low cytotoxicity.
authors.affiliation: Chemistry Department, Faculty of Science, Alexandria University, Egypt.
authors.forename: E S
authors.initials: ES
authors.lastname: el Ashry
authors.forename: A A
authors.initials: AA
authors.lastname: Abdel-Rahman
authors.forename: N
authors.initials: N
authors.lastname: Rashed
authors.forename: H A
authors.initials: HA
authors.lastname: Rasheed
mesh_terms: D000212:Acyclovir / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology*; D000998:Antiviral Agents / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D004261:DNA Replication / Q000187:drug effects; D004279:DNA, Viral / Q000096:biosynthesis; D006515:Hepatitis B virus / Q000187:drug effects*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D016133:Polymerase Chain Reaction
chemical_list: D000998:Antiviral Agents; D004279:DNA, Viral; D000212:Acyclovir