Synthesis and In Silico Study of 4-Substituted 1-Aminoanthraquinones

Shupeniuk, V. I.; Amaladoss, N.; Taras, T. N.; Sabadakh, O. P.; Matkivskyi, N. P.

Eight new 4-substituted 1-amino-9,10-anthraquinones containing a primary amino group were syn­the­sized by nucleophilic substitution of bromine in 1-amino-4-bromo-9,10-anthraquinones. 1-Amino-4-[2-(hy­droxy­ethyl)amino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid containing a biogenic amine fragment (2-aminoethanol) was converted into the corresponding 1-triazenyl derivatives. The structure of the synthesized compounds was determined on the basis of the LC/MS and (13)C and (1)H NMR data, and their drug likeness was estimated in silico. Compounds with a good drug likeness score were analyzed by DIGEP-Pred, their possible interactions with proteins were simulated using STRING, and their biological activity was interpreted using the Kyoto Encyclopedia of Genes and Genomes.