Effect of substituents in the A and B rings of chalcones on antiparasite activity

Abstract

Chalcones are a group of natural products with many recognized biological activities, including antiparasitic activity. Although a lot of chalcones have been synthetized and assayed against parasites, the number of structural features known to be involved in this biological property is small. Thus, in the present study, 21 chalcones were synthesized to determine the effect of substituents in the A and B rings on the activity against Leishmania braziliensis, Trypanosoma cruzi, and Plasmodium falciparum. The compounds were active against L. braziliensis in a structure-dependent manner. Only one compound was very active against T. cruzi, but none of them had a significant antiplasmodial activity. The electron-donating substituents in ring B and the hydrogen bonds at C-2′ with carbonyl affect the antiparasitic activity.

Chalcones: Synthetic Chemistry Follows Where Nature Leads

“…Another derivative (211) (Figure 18) showed significant trypanocidal activity (IC 50 = 2.6 µM). These are just a few examples of antiparasitic synthetic chalcone derivatives, and there are many more examples are available in the literature [123,124]. Quinolinone-chalcone derivatives were synthesized and assessed for their antiparasitic activity against the mammalian stages of Trypanosoma brucei and Leishmania infantum [122].…”

“…Another derivative (211) (Figure 18) showed significant trypanocidal activity (IC50 = 2.6 μM). These are just a few examples of antiparasitic synthetic chalcone derivatives, and there are many more examples are available in the literature [123,124].…”

Synthesis and Evaluation of Trypanocidal Activity of Chromane-Type Compounds and Acetophenones

“…In the chromones ( 10 – 13 series B and 23 – 26 series D), chalcones and flavonoid compounds ( 27 and 28 series E and 29 and 30 series F), the activity is only marginal, except for compound 28 which has in addition to a p-chlorophenyl group and the αβ-unsaturated carbonyl group which has already been demonstrated to be important in antiparasitic activity [ 16 ].…”

Quantum mechanical, molecular docking, molecular dynamics, ADMET and antiproliferative activity onTrypanosoma cruzi(Y strain) of chalcone (E)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one derived from a natural product

“…Cell death events in T. cruzi induced by CPN 3 NO 2 were evaluated using 7-aminoactinomycin D (7-AAD) and annexin V (AX) conjugated with phycoerythrin. 7-AAD binds to the DNA in cells that lost its membrane integrity, while AX binds to phosphatidylserine, a membrane phospholipid that is externalized during the programmed cell death pathway 12,13 [1, 2]. For this, 10 6 epimastigote mL −1 were incubated in 24-well plates with CPN 3 NO 2 (62.5; 125 and 250 μM) for 24 hours in a BOD incubator.…”

“…11 21 chalcones were synthesized to determine the effective activity against T. cruzi , and some showed selective activity against Trypanosoma parasites. 12 The phytochemical evaluation of the Polygonum salicifolium yielded two chalcones that showed good anti-titrypanosomal activity. 13 New prenylated synthetic chalcones have shown an effect on the viability of T. cruzi parasites.…”