ABSTRACT
Triterpene derivatives with an α,ß-alkenenitrile moiety in the five-membered ring A have been synthesized by nitrile anion cyclizations of 1-cyano-2,3-secotriterpenoids. Oxime-containing precursors, 2,3-secointermediates and five-membered ring A products of cyclizations were screened for in vitro antiviral activity against enveloped viruses - influenza A virus and human immunodeficiency virus type I (HIV-1). Lupane ketoxime and the 2,3-secolupane C-3 aldoxime which possess antiviral activities against both influenza A virus (EC50 12.9-18.2 µM) and HIV-1 (EC50 0.06 µM) were the most promising compounds.
Subject(s)
Antiviral Agents/chemistry , Antiviral Agents/pharmacology , Terpenes/chemistry , Terpenes/pharmacology , Cyclization , HIV-1/drug effects , Influenza A Virus, H7N1 Subtype/drug effects , Models, Molecular , Molecular Conformation , Oximes/chemistryABSTRACT
The ability of ascorbic acid and a number of its derivatives to suppress replication of Herpes simplex virus type I was investigated in human rhabdomyosarcoma cell line. In parallel, interaction of the test compounds with carbon- and oxygen-centered radicals formed on radiolysis of hydroxyl-containing organic compounds was studied using the steady state radiolysis method. It has been shown that 2-O-glycoside of ascorbic acid, displaying marked antiviral properties against Herpes simplex virus type I, is also capable of inhibiting fragmentation and recombination reactions of α-hydroxyl-containing carbon-centered radicals while not affecting processes involving oxygen-centered radicals.
