title: Synthesis of some acylphosphonate thiosemicarbazones and evaluation of their antiviral activity.
abstract: Reaction of dimethyl acylphosphonates (1) with thiosemicarbazide afforded the corresponding dimethyl acylphosphonate thiosemicarbazones (4). Lithium methyl acylphosphonate thiosemicarbazones (5) could be prepared either by monodealkylating compounds 4 by lithium bromide or by reacting lithium methyl acylphosphonates with thiosemicarbazide. Dihydrogen acylphosphonate thiosemicarbazones (6) could be obtained by reacting acylphosphonic acids (3) with thiosemicarbazide. The alternative approach to 6 by di-dealkylating compounds 4 using bromotrimethylsilane was limited by the solubility properties of esters 4. Compounds of types 5 and 6 did not show antiviral activity against herpes simplex type 1 and 2, or toward vaccinia virus.
authors.affiliation: Department of Pharmaceutical Chemistry, Hebrew University School of Pharmacy, Jerusalem, Israel.
authors.forename: E
authors.initials: E
authors.lastname: Breuer
authors.forename: R
authors.initials: R
authors.lastname: Karaman
authors.forename: H
authors.initials: H
authors.lastname: Zaher
authors.forename: E
authors.initials: E
authors.lastname: Katz
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D018259:Herpesvirus 1, Human / Q000187:drug effects / Q000254:growth & development; D018258:Herpesvirus 2, Human / Q000187:drug effects / Q000254:growth & development; D008720:Methisazone / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018139:Simplexvirus / Q000187:drug effects* / Q000254:growth & development; D013329:Structure-Activity Relationship; D013882:Thiosemicarbazones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014616:Vaccinia virus / Q000187:drug effects* / Q000254:growth & development; D010948:Viral Plaque Assay
chemical_list: D000998:Antiviral Agents; D063065:Organophosphonates; D013882:Thiosemicarbazones; D008720:Methisazone