title: Synthesis of phosphonate 3-phthalidyl esters as prodrugs for potential intracellular delivery of phosphonates.
abstract: A new prodrug approach for intracellular delivery of phosphonates was developed via the synthesis of 3-phthalidyl esters of 1-naphthalenemethylphosphonate. This approach is advantageous over the traditional acyloxymethyl phosphonate prodrugs, because these prodrugs do not generate formaldehyde and have improved plasma half-lives.
authors.affiliation: Department of Medicinal Chemistry, Metabasis Therapeutics, Inc., San Diego, CA 92121, USA.
authors.forename: Q
authors.initials: Q
authors.lastname: Dang
authors.forename: B S
authors.initials: BS
authors.lastname: Brown
authors.forename: P D
authors.initials: PD
authors.lastname: van Poelje
authors.forename: T J
authors.initials: TJ
authors.lastname: Colby
authors.forename: M D
authors.initials: MD
authors.lastname: Erion
mesh_terms: D000818:Animals; D004952:Esters / Q000097:blood / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D007700:Kinetics; D008099:Liver / Q000187:drug effects; D009281:Naphthalenes / Q000737:chemistry; D063065:Organophosphonates / Q000097:blood / Q000493:pharmacokinetics / Q000494:pharmacology*; D011355:Prodrugs / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D051381:Rats
chemical_list: D004952:Esters; D009281:Naphthalenes; D063065:Organophosphonates; D011355:Prodrugs; C031721:naphthalene