Synthesis of some acylphosphonate thiosemicarbazones and evaluation of their antiviral activity.
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.
Breuer
E
E
Department of Pharmaceutical Chemistry, Hebrew University School of Pharmacy, Jerusalem, Israel.
Karaman
R
R
Zaher
H
H
Katz
E
E
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
D000998:Antiviral Agents; D063065:Organophosphonates; D013882:Thiosemicarbazones; D008720:Methisazone