Anti-Parasite Activity of Novel 3,5-Diiodophenethyl-benzamides

Abstract

Novel iodotyramides with para-substituted benzoic acids were synthesized via electrophilic aromatic substitutions and amide coupling via N,N'-diisopropylcarbodiimide (DIC) in dimethylformamide (DMF). All derivatives were in vitro screened against U-937 macrophages and Plasmodium falciparum, Leishmania panamensis and Trypanosoma cruzi protozoan parasites. The hemolytic activity was evaluated on human red blood cells (RBC). -methoxyphenethyl)-4-methoxybenzamide were the most active against L. panamensis with an effective concentration 50 (EC 50 ) of 17.9 and 17.5 μg mL -1 , respectively; while compounds N- (3,5-diiodo-4-methoxyphenethyl)-4-methylbenzamide and N-(3,5-diiodo-4-methoxyphenethyl

Ascidian halogen-containing secondary metabolites from the family didemnidae

“…When tested on rats injection of 5′-deoxy-5-iodotubercidin reduced blood pressure and heart rate (Davies et al, 1986). ethyl] benzamide (30), a natural product from D. rubeum, showed moderate activity against Leishmania panamensis and Trypanosoma cruzi, and high activity against Plasmodium falciparum (Restrepo et al, 2019). Compound 30 exerted strong toxicity towards brine shrimps (Artemia salina), the determined lethal concentration was lower than those of known toxicants (LD 50 =20 µM).…”

“…The iodination of the aromatic ring was accomplished with N-iodosuccinimide and acid hydrolysis of this product gave the iodinated amine. The amide synthesis was done by DIC-coupling of the desired amine with benzoic acid (Restrepo et al, 2019). -[2-(3,5-diiodo-4-methoxyphenyl)ethyl] benzamide (30).…”