Synthesis and antiviral activity of 2-phenoxymethyl derivatives of 5-hydroxyindole

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

“…In the case of the 4-dimethylaminomethyl derivatives of substituted 5-hydroxyindoles it was shown that they also exhibit activity against influenza, but this is no higher than the activity of rimantadine [41,54]. Another compound of this series arbidol (6-bromo-5-hydroxy-4-dimethylaminomethyl-1-methyl-2-phenylthiomethyl-3-ethoxycarbonylindole) proved a highly effective product with antiviral, interferon-inducing, and immunostimulant activity [81][82][83].…”

“…As a rule, for 5-hydroxyindoles the Mannich reaction goes preferentially at position 4. Actually, in the absence of substituents at position 3, for example, aminomethylation with bisdimethylaminomethane goes regioselectively at position 4 with yields close to quantitative [39][40][41], which could apparently be determined by purely steric factors. However, formation of the corresponding 4-isogramine (which has been proposed as an antiinflammatory agent) was also noticed for the 3-substituted 5-hydroxyindole 3-acetyl-5-hydroxy-2-(sulfanylmethyl)indole, in spite of the presence of the acetyl group at position 3 [42].…”

“…Of course, the only possibility for 1,2,3,6-tetrasubstituted [46][47][48][49][50][51][52] and 1,2,3,6,7-pentasubstituted [18] 5-hydroxyindoles is dimethylaminomethylation at position 4. This method was used for the synthesis of arbidol, labelled with C 14 at position 2 and at the ethoxycarbonyl group, in order to study its pharmacokinetics [53].…”

A novel one pot Mannich synthesis of methylpiperidin phenols, methylphenylmorfolin phenols and methyltiophenylmorpholin phenols solvent-free and using infrared light irradiation

“…The most common solvents using in this reaction are alcohols such as methanol and ethanol, but benzene and aprotic solvents are also used [29][30][31][32][33][34] . Methylphenylmorpholinyl phenol derivatives have been used as ligands in zinc complexes 35 , and some of them show gastrokinetic activity 36 , as antiviral agents 37 , as antimalaria agents 38 as spermicides 39 and also as antiarrhythmic agents 40 . Some piperidine derivatives have been used in the treatment of heart disease, as a remedy for auricular fibrillation 41 , and as insect repellents 42 .…”