Bis(alkylaminoalkoxy-2-benzofuranyl)ketone (IIa-o) were synthesized by the reaction of alkylaminoalkyl halide with bis(hydroxy-2-benzofuranyl)ketones (I). Bis(alkylaminoalkoxy-2-benzofuranyl)keton N, N-dioxides (IIIa, b) were prepared from II by treatment with hydrogen peroxide. Bis(acyloxy-2-benzofuranyl)ketones (IVa-q) were synthesized by the reaction of acid chloride and acid anhydride with I. Bis(6-acetoxy-2-benzofuranyl)ketone (IVb) showed the most potent inhibitory activity on the multiplication of influenza virus in vitro. Bis(7-diethylaminoethoxy-2-benzofuranyl)ketone N, N-dioxide (IIIa) showed a potent interferon inducing activity in mice. IVb and IIIa given orally were effective against the infection of an influenza virus in mice.
