Synthesis of leading chalcones with high antiparasitic, against Hymenolepis nana, and antioxidant activities

Abstract

The hymenolepiosis by Hymenolepis nana is a major public health problem in developing countries, and the commercial drugs against this parasitosis are not enough effective. The combination of antiparasitic and antioxidant agents has improved the treatment of some parasitoses. Thus, the development of new cestocidal and antioxidant agents to treat the hymenolepiosis cases is important. In the present study, four hydroxy-and four dihydroxy-chalcones were synthesized using the catalyst boron trifluoride diethyl etherate (BF 3 •OEt 2 ). The antioxidant activity and antiparasitic against H. nana of chalcones were tested, as well as the toxicity by the brine shrimp lethality bioassay and the method of Lorke. The antioxidant activity was measured by three radical scavenging assays: 2,2'-azino-bis-3-ethylbenzothiazoline-6sulphonic acid (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and ferric reducing antioxidant power (FRAP). The hydroxyl substitution pattern (number and position), mainly in ring B, was responsible for the chalcone antiparasitic activity. At least one meta or para hydroxyl group in ring B was essential for activity of the synthetic chalcones against H. nana; The time taken for the parasite to die by the 3b and 3e chalcones (20 mg/mL) treatment was up to six times lower than the control drug Praziquantel. On the other hand, chalcones with catechol structure in ring B (3g and 3h) showed the highest antioxidant values. The toxicity evaluations suggests that synthetic hydroxychalcones with cestocidal (3b and 3e) and antioxidant (3g and 3h) activities are safe compounds and potential in vivo agents to treat this parasitosis.

Recent Advances in Chalcones: Synthesis, Transformation and Pharmacological Activities

“…Díaz-Carrillo et al found out the number and position of hydroxyl substituent in ring B to be responsible for the chalcone antiparasitic activity of chalcones 105 and 106 which at 20 mg/mL was able to kill the parasite at the lesser treatment time about six times lower than the control drug Praziquantel. In conclusion, at least one meta or para hydroxyl group in ring B was adequate for the activity of the synthetic chalcones against H. nana parasite [27] (Fig. 9).…”

“…In another investigation, Lahsasni and coworkers, surprisingly found compound 107 (68.58% at C = 2μg/ml) more effective as an antioxidant agent than the ascorbic acid [26]. Meanwhile, the meta-and para-dihydroxy substitution patterns in ring B of chalcones (catechol structure in ring B) 108 were the best combinations for the highest antioxidant activity compared to caffeic acid (positive control) [27].…”

“…Chalcones are multifunctional molecules that possess promising pharmacological activities. Chalcones have been found useful as anticancer [23][24][25], antioxidant [26][27][28][29], antiinflammatory [30][31][32], anti-microbial [23,[33][34][35][36], anti-tubercular [34,37,38], antileishmanial [39], antimalarial [40][41][42], anthelmintic [27], osteogenic activity [43]. This review article focuses on recent applications of Claisen-Schmidt condensation reaction employed in the synthesis of chalcone, its transformation to heterocyclic compounds and pharmacological activities.…”

Evaluation of Chalcone Derivatives as Photosynthesis and Plant Growth Inhibitors

“…[36,37] Due to their potent capacity to scavenge reactive oxygen species as well as the electrophilic nature of the α,βunsaturated ketone moiety, chalcones have also been used as antioxidant agents. [38][39][40] Therefore, considering the electronic properties of chalcone derivatives such as electron acceptor, it is relevant to investigate the effects of these compounds as electron transport chain inhibitors, blocking electron flow through photosystem II (PS II). In this work, we set out to evaluate chalcone derivatives containing aromatic rings bearing electron donating and withdrawing groups as well as heteroaromatic rings in post-emergent herbicide assays such as photosynthesis and plant growth inhibition.…”

“…Additionally, chalcones can be readily synthetized through a wide array of methodologies, [25] providing easy access to a broad structural diversity, and thus affording a variety of biological activities, [26] as anti‐inflammatory, [27,28] antitumoral, [29] antiviral, [30] insecticide, [31,32] nematicide, [33] larvicide [34,35] and herbicide [36,37] . Due to their potent capacity to scavenge reactive oxygen species as well as the electrophilic nature of the α,β‐unsaturated ketone moiety, chalcones have also been used as antioxidant agents [38–40] . Therefore, considering the electronic properties of chalcone derivatives such as electron acceptor, it is relevant to investigate the effects of these compounds as electron transport chain inhibitors, blocking electron flow through photosystem II (PS II).…”