Novel quinoline derivatives with broad‐spectrum antiprotozoal activities

Hartman, Carla B.; Dube, Phelelisiwe S.; Legoabe, Lesetja J.; Van Pelt, Natascha; Matheeussen, An; Caljon, Guy; Beteck, Richard M.

doi:10.1002/ardp.202300319

Cited by 2 publications

(1 citation statement)

References 42 publications

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“…Years of scientific research have revealed that chalcones exhibit diverse biological activities ( Rajendran et al, 2022 ; Hartman et al, 2024 ; Yousefian et al, 2024 ), with antioxidant ( Jung et al, 2017 ), antimicrobial ( Zhou et al, 2021 ), anti-inflammatory, antitumor ( Neves et al, 2012 ), anti-infective ( Nowakowska, 2007 ), anticancer ( Binate and Ganbarov, 2023 ), antiviral ( Hu et al, 2023 ), cytotoxic ( Vogel and Heilmann, 2008 ), antiallergic ( Escribano-Ferrer et al, 2019 ), antituberculosis ( Verma et al, 2018 ), and antibacterial ( Nielsen et al, 2005 ; Wang et al, 2023 ; Zhang et al, 2024 ) properties. Chalcones are small, achiral molecules that have molecular weights in the range of 300–600 g/mol and exhibit relatively high lipophilicities ( Nowakowska, 2007 ).…”

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confidence: 99%

Green synthesis, structure–activity relationships, in silico molecular docking, and antifungal activities of novel prenylated chalcones

Godara,

Kaushik,

Tripathi

et al. 2024

Front. Chem.

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A series of 16 novel prenylated chalcones (5A-5P) was synthesized by microwave-assisted green synthesis using 5-prenyloxy-2-hydroxyacetophenone and different benzaldehydes. Comparisons were also performed between the microwave and conventional methods in terms of the reaction times and yields of all compounds, where the reaction times in the microwave and conventional methods were 1–4 min and 12–48 h, respectively. The synthesized compounds were characterized using different spectroscopic techniques, including IR, 1H-NMR, 13C-NMR, and LC-HRMS. The antifungal activities of all compounds were evaluated against Sclerotium rolfsii and Fusarium oxysporum under in vitro conditions and were additionally supported by structure–activity relationship (SAR) and molecular docking studies. Out of the 16 compounds screened, 2’-hydroxy-4-benzyloxy-5’-O-prenylchalcone (5P) showed the highest activity against both S. rolfsii and F. oxysporum, with ED50 of 25.02 and 31.87 mg/L, respectively. The molecular docking studies of the prenylated chalcones within the active sites of the EF1α and RPB2 gene sequences and FoCut5a sequence as the respective receptors for S. rolfsii and F. oxysporum revealed the importance of the compounds, where the binding energies of the docked molecules ranged from −38.3538 to −26.6837 kcal/mol for S. rolfsii and −43.400 to −23.839 kcal/mol for F. oxysporum. Additional docking parameters showed that these compounds formed stable complexes with the protein molecules.

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Section: Introductionmentioning

confidence: 99%

Green synthesis, structure–activity relationships, in silico molecular docking, and antifungal activities of novel prenylated chalcones

Godara,

Kaushik,

Tripathi

et al. 2024

Front. Chem.

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Hydrazinated geraniol derivatives as potential broad‐spectrum antiprotozoal agents

Jooste,

Legoabe,

Ilbeigi

et al. 2024

Archiv der Pharmazie

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Geraniol, a primary component of several essential oils, has been associated with broad‐spectrum antiprotozoal activities, although moderate to weak. This study primarily concentrated on the synthesis of hydrazinated geraniol derivatives as potential antiprotozoal agents. The synthesised compounds were tested in vitro against different parasitic protozoans of clinical relevance, including Trypanosoma brucei brucei, Trypanosoma brucei rhodesiense, Trypanosoma cruzi and Leishmania infantum. Compounds 6, 8, 13, 14 and 15 demonstrated low micromolar activity against the different parasites. Compounds 8, 13, 14 and 15 had the highest efficacy against Trypanosoma brucei rhodesiense, as indicated by their respective IC50 values of 0.74, 0.56, 1.26 and 1.00 µM. Compounds 6, 14 and 15 displayed the best activity against Trypanosoma brucei brucei, with IC50 values of 1.49, 1.48 and 1.85 µM, respectively. The activity of compounds 6, 14 and 15 also extended to intracellular Trypanosoma cruzi, with IC50 values of 5.14, 6.30 and 4.90 µM, respectively. Compound 6, with an IC50 value of 11.73 µM, and compound 14, with an IC50 value of 8.14 µM, demonstrated some modest antileishmanial activity.

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Novel quinoline derivatives with broad‐spectrum antiprotozoal activities

Cited by 2 publications

References 42 publications

Green synthesis, structure–activity relationships, in silico molecular docking, and antifungal activities of novel prenylated chalcones

Green synthesis, structure–activity relationships, in silico molecular docking, and antifungal activities of novel prenylated chalcones

Hydrazinated geraniol derivatives as potential broad‐spectrum antiprotozoal agents

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