Synthesis and antimalarial activity of urenyl Bis-chalcone in vitro and in vivo

Domínguez, José N.; Domínguez, Neira Gamboa de; Rodrígues, Juan; Acosta, María Eugenia; Caraballo, Noris; León, Caritza

doi:10.3109/14756366.2012.733383

Cited by 13 publications

(6 citation statements)

References 25 publications

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“…It was noted that 3,4,5-trimethoxy series of derivatives displayed weak activity, probably because of the stearic hindrance at the binding site of the enzyme. Several dimeric chalcone derivatives were synthesized and their antimalarial potential was evaluated using in vitro globin hydrolysis, β-hematin formation, and murine Plasmodium berghei [121]. Among the deimeric chalcone derivatives, 1,1-bis-[(3 ,4 -N-(urenylphenyl)-3-(3",4",5"-trimethoxyphenyl)]-2-propen-1-one (209) (Figure 18) was found to be the most active antimalarial candidate.…”

Section: Antiparasitic Activitymentioning

confidence: 99%

Chalcones: Synthetic Chemistry Follows Where Nature Leads

et al. 2021

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Chalcones belong to the flavonoid class of phenolic compounds. They form one of the largest groups of bioactive natural products. The potential anticancer, anti-inflammatory, antimicrobial, antioxidant, and antiparasitic properties of naturally occurring chalcones, and their unique chemical structural features inspired the synthesis of numerous chalcone derivatives. In fact, structural features of chalcones are easy to construct from simple aromatic compounds, and it is convenient to perform structural modifications to generate functionalized chalcone derivatives. Many of these synthetic analogs were shown to possess similar bioactivities as their natural counterparts, but often with an enhanced potency and reduced toxicity. This review article aims to demonstrate how bioinspired synthesis of chalcone derivatives can potentially introduce a new chemical space for exploitation for new drug discovery, justifying the title of this article. However, the focus remains on critical appraisal of synthesized chalcones and their derivatives for their bioactivities, linking to their interactions at the biomolecular level where appropriate, and revealing their possible mechanisms of action.

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Section: Antiparasitic Activitymentioning

confidence: 99%

Chalcones: Synthetic Chemistry Follows Where Nature Leads

et al. 2021

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“…In an another study, 1, 1- Bis -[(3′,4′- N -(urenylphenyl)-3-(3″,4″,5″-trimethoxyphenyl)]-2-propen-1-one, identified as the most active by in vitro tests, and was tested in mice infected with P. berghei (ANKA), a chloroquine-susceptible strain of murine malaria. This compound was able to decrease the parasitemia and delay the progression of malaria but did not eradicate the infection [ 28 ]. So, with these rationales, the present study primarily aimed to find antimalarial potential in a malaria mouse model and was further extended to find whether these chalcones can modulate the immune response or not.…”

Section: Introductionmentioning

confidence: 99%

Antimalarial and immunomodulatory potential of chalcone derivatives in experimental model of malaria

Sinha

Medhi

Radotra

et al. 2022

BMC Complement Med Ther

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Background Malaria is a complex issue due to the availability of few therapies and chemical families against Plasmodium and mosquitoes. There is increasing resistance to various drugs and insecticides in Plasmodium and in the vector. Additionally, human behaviors are responsible for promoting resistance as well as increasing the risk of exposure to infections. Chalcones and their derivatives have been widely explored for their antimalarial effects. In this context, new derivatives of chalcones have been evaluated for their antimalarial efficacy. Methods BALB/c mice were infected with P. berghei NK-65. The efficacy of the three most potent chalcone derivations (1, 2, and 3) identified after an in vitro compound screening test was tested. The selected doses of 10 mg/kg, 20 mg/kg, and 10 mg/kg were studied by evaluating parasitemia, changes in temperature, body weights, organ weights, histopathological features, nitric oxide, cytokines, and ICAM-1 expression. Also, localization of parasites inside the two vital tissues involved during malaria infections was done through a transmission electron microscope. Results All three chalcone derivative treated groups showed significant (p < 0.001) reductions in parasitemia levels on the fifth and eighth days of post-infection compared to the infected control. These derivatives were found to modulate the immune response in a P. berghei infected malaria mouse model with a significant reduction in IL-12 levels. Conclusions The present study indicates the potential inhibitory and immunomodulatory actions of chalcones against the rodent malarial parasite P. berghei.

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“…Chalcones are a fascinating multifunctional class of compounds that have a broad spectrum of established biological activities in a range of diseases and several mechanisms of actions [16]. Its pharmacological activities were reported in numerous disease conditions such as hypertension, infectious diseases, neurological disorders and cancer [17][18][19][20][21][22]. Few chalcones were tested in clinical trials for the treatment of chronic venous insufficiency and Helicobacter pylori infection [23][24][25].…”

Section: Introductionmentioning

confidence: 99%

Targeting triple negative breast cancer heterogeneity with chalcones: a molecular insight

Alali

Moustafa

Khalil

2019

Journal of Drug Targeting

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Triple negative breast cancers (TNBCs) are aggressive heterogeneous cancers with not yet determined conventional targeted medication. Therefore, identification of new alternatives or improved treatment options to combat this deadly disease is highly needed. On the other hand, various derived products with chalcone scaffold were historically considered excellent candidates for the development of anticancer drugs. Chalcones unique chemical structure and their substantial biological activities in cancer cells make them an extremely attractive target for the treatment of several human carcinomas including TNBCs. This review highlights the promising therapeutic role of chalcones in TNBC management.

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Synthesis and antimalarial activity of urenyl Bis-chalcone in vitro and in vivo

Cited by 13 publications

References 25 publications

Chalcones: Synthetic Chemistry Follows Where Nature Leads

Chalcones: Synthetic Chemistry Follows Where Nature Leads

Antimalarial and immunomodulatory potential of chalcone derivatives in experimental model of malaria

Targeting triple negative breast cancer heterogeneity with chalcones: a molecular insight

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