Open AccessSynthesis of N-[3-(2,3-dimethyl-1H-indol-1-yl)-4-hydroxyphenyl]arylsulfon(aroyl)amides
Author(s) -
A. P. Avdeenko,
S. A. Konovalova,
I. Yu. Yakymenko
Publication year - 2020
Publication title -
voprosy himii i himičeskoj tehnologii/voprosy himii i himičeskoj tehnologii
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.278
H-Index - 7
eISSN - 2413-7987
pISSN - 0321-4095
DOI - 10.32434/0321-4095-2020-133-6-20-25
Subject(s) - chemistry , steric effects , ring (chemistry) , indole test , redox , medicinal chemistry , sulfonamide , benzoic acid , benzene , stereochemistry , naphthalene , condensation reaction , organic chemistry , catalysis
Indole derivatives are an essential elements of many natural and synthetic compounds having significant biological activity. New derivatives of 2,3-dimethylindole were synthesized in this work by the reaction of N-(4-oxocyclohexa-2,5-dien-1-ylidene)arylsulfon(aroyl)amides and 4-methyl-N-(4-oxonaphthalen-1(4H)-ylidene)benzene-1-sulfonamide with 2,3-dimethylindole. The possibility of these reactions is determined by the redox potential of the starting amides and steric factor. If there is a free C=C bond in the quinoid ring of the starting arylsulfonamides, the reaction proceeds under the 1,4-addition scheme with the formation of corresponding N-[3-(2,3-dimethyl-1H-indol-1-yl)-4-hydroxyphenyl(naphthyl-1)]arylsulfonamides which are potentially biologically active compounds. N-(4-Oxocyclohexa-2,5-diene-1-ylidene)aroylamides have a high redox potential as compared with similar arylsulfonamides and naphthalene derivatives; therefore, two processes proceed in their reaction with 2,3-dimethylindole: reduction and 1,4-addition. The 1,4-addition product was obtained only for the 2,3-dimethyl derivative, which has the lowest redox potential among the investigated aroylamides. Analysis of the potential biological activity of the synthesized compounds by using the PASS program showed that the synthesized products can exhibit the following activities: para amino benzoic acid antagonist, glutamyl endopeptidase II inhibitor, CYP3A2 substrate, insulysin inhibitor, membrane integrity agonist and phobic disorders treatment.