Aminoalkyl-5- and -6-hydroxyindoles and their antiviral activity

Methods for the Synthesis of Isogramines and Their Chemical Properties. (Review)

“…Thus, for example, there data on the antiviral activity of 1,3,5-trisubstituted 2-diethylaminomethylindoles [22,23]. Activity against the influenza virus was exhibited by the hydrochloride of 5-acetoxy-1-benzyl-6-bromo-2-dimethylaminomethyl-3-ethoxycarbonylindole [19].…”

“…Thus, the action of aqueous dimethylamine on 2-bromomethyl-1,3-dibenzoylindole leads to the initial formation of 3-benzoyl-2-dimethylaminomethylindole, the debenzoylation of which with p-toluenesulfonic acid in ethylene glycol gives unsubstituted 2-isogramine [15]. The corresponding 2-dialkylaminomethyl derivatives were obtained by the analogous reaction of substituted 2-bromomethylindoles with dimethylamine [16][17][18][19][20][21] and diethylamine [22,23]. By this procedure it is possible to obtain unsubstituted 2-isogramine (3) from 2-methyl-3-phenylthioindole (6) using the following sequence of transformations [16] …”