Studies on the Syntheses and Antiviral Effect of 3-Alkylphenoxy- and 3-Alkanoylaminophenoxy-1, 2-propanediols

Abstract

Under the assumption that compounds with hydrophobic group would have antiviral activity, the compounds of 3-(o-alkylphenoxy)-, 3-(p-alkylphenoxy)-, and 3-(o-alkanoylaminophenoxy)-1, 2-propanediol series were synthesized and examined for antiviral activities. 3-Alkylphenoxy-1, 2-propanediols were prepared from fatty acid phenyl esters by their Fries rearrangement to o- and p-alkanoylphenols, Clemmensen reduction to o- and p-alkylphenols, and condensation with 3-chloro-1, 2-propanediol in the presence of sodium ethoxide in ethanol to 3-(o-alkylphenoxy)-and 3-(p-alkylphenoxy)-1, 2-propanediols having alkyl chains of 6∼14 carbon atoms. 3-(o-Alkanoylaminophenoxy)-1, 2-propanediols having alkanoyl chains of 8∼12 carbon atoms were prepared by the condensation of o-alkanoylaminophenols with 3-chloro-1, 2-propanediol in the presence of sodium ethoxide in ethanol. 3-(o-Decanoylaminophenoxy)-1, 2-propanediol had antiviral activity against the Nakayama strain of Japanese B encephalitis virus in vivo. Several compounds of 3-(p-alkylphenoxy)- and 3-(o-alkylphenoxy)-1, 2-propanediol series had antiviral activity against the Lansing strain of poliomyelits virus in vitro.