Synthesis, characterization and evaluation of prenylated chalcones ethers as promising antileishmanial compounds

Effects of Synthetic Ligustrazine-Based Chalcone Derivatives on Trypanosoma brucei brucei and Leishmania spp. Promastigotes

“…Twenty-five new prenylated chalcones [ 22 ] with antiparasitic efficacy against Leishmania mexicana were recently synthesized. The selectivity index (SI) values for these chalcones were also the highest.…”

“…In addition, homology modeling was used to generate a three-dimensional structure of L. mexicana fumarate reductase. According to docking studies, prenylated chalcones have the potential to regulate fumarate reductase activity by binding to two essential binding sites [ 22 ].…”

Antiviral and antimicrobial applications of chalcones and their derivatives: From nature to greener synthesis

“…Eleven derivatives showed a metabolic inhibition of at least 50% and three of the most potent ones had IC 50 values less than 10 μM. According to docking studies, prenylated chalcones may affect fumarate reductase activity by binding with high affinity to two binding sites that are essential for the target [ 157 ]. In another work, six chalcone derivatives were designed and developed using a drug-food-homologous chalcone skeleton, and nearly half of the compounds demonstrated effective anti- Toxoplasma activity in vitro .…”

“… “( E )-1-(2-hydroxy-4-methoxyphenyl)-3-(2-methoxyphenyl)prop-2-en-1-one” Trypanosoma brucei brucei , Trypanosoma congolense , and Leishmania Mexicana In vitro EC 50 : 0.5, 2.5, and 5.2 μg/mL, respectively N/A [ 156 ] “( E )-1-(3-methoxy-4-((3-methylbut-2-en-1-yl)oxy) phenyl)-3-(3-nitrophenyl)prop-2-en-1-one” “( E )-1-(3-methoxy-4-((3-methylbut-2-en-1-yl)oxy) phenyl)-3-(3-(trifuoromethyl)phenyl)prop-2-en-1-one” “( E )-3-(3-methoxy-4-((3-methylbut-2-en-1-yl)oxy) phenyl)-1-(2-(trifuoromethyl)phenyl)prop-2-en-1-one” L. mexicana In vitro, In silico IC 50 < 10 μM Possibly modulates the activity of fumarate reductase by binding to two crucial binding sites for the target with good affinity. [ 157 ] “(E)-3-(2-bromophenyl)-1-(4-(isopropylamino)phenyl)prop2-en-1-one” “(E)-3-(2-bromophenyl)-1-(4-(ethylamino)phenyl)prop-2-en1-one” Toxoplasma gondii In vitro, In vivo Significant anti-toxoplasma activity and reduction of biochemical variables as well as liver and spleen indices Anti-Toxoplasma effects are enhanced by the Michael receptor found in chalcones' molecular skeleton. [ 158 ] Chalcone derivatives with substituents in the A and B rings “1‐(2‐Aminophenyl)‐3‐(3,4,5‐trimethoxyphenyl)prop‐2‐en‐1‐one” “1‐(2‐Aminophenyl)‐3‐(3,5‐dimethoxyphenyl)prop‐2‐en‐1‐one” “1‐(2‐Hydroxyphenyl)‐3‐(3,4,5‐trimethoxyphenyl)prop‐2‐en‐1‐one” Leishmania braziliensis , Trypanosoma cruzi , Plasmodium falciparum In vitro EC 50 : 5.7 against L. braziliensis ; EC 50 against T. cruzi : 8.1 μM; EC 50 against P. falciparum : 59.2 μM The antiparasitic properties were affected by the hydrogen bonds at C-2′ with carbonyl and the electron-donating substituents in ring B.…”

Potent Anthelmintic Activity of Chalcones Synthesized by an Effective Green Approach

“…Chalcones have emerged as promising lead molecules in the fight against various parasitic infections, [27–31] including those caused by parasitic nematodes [32,33] . Hybrid benzimidazolyl‐chalcones and derivatives have demonstrated in vitro nematocidal activity against Haemonchus contortus [34] .…”