Rapid synthesis and antifungal evaluation of prenylated chalcones: A structure-activity relationship and molecular docking study
Year: 2024
Type: article
Abstract: Microwave-assisted green chemistry was employed to synthesize a series of prenylated chalcones, resulting from the reaction of 4-prenyloxy-2-hydroxy-acetophenone with diverse benzaldehydes. A comparative analysis of reaction times and yields revealed significant advantages of the microwave method, with reaction times ranging from 1 to 3.2 minutes, compared to 12 to 48 hours using conventional methods. The structural elucidation of the synthesized compounds was achieved through a combination of spectroscopic techniques, including IR, 1H NMR, 13C NMR and LC-HRMS. In vitro antifungal assays were performed against Sclerotium rolfsii and Fusarium oxysporum to evaluate the efficacy of these compounds, which was further supported by SAR analysis and molecular docking studies. The most effective compound against S. rolfsii, was found to be 2’-Hydroxy-4-bromo-4’-O-prenylchalcone (5E) with ED50= 23.28 mg L−1, while 2’-Hydroxy-2,6-dichloro-4’-O-prenylchalcone (5B) (ED50= 25.70 mg L−1) exhibited the highest activity against F. oxysporum. The molecular docking studies for targeting two different fungi, namely, S. rolfsii (DNA directed RNA polymerase: RPB2 gene target) and F. oxysporum (Cutinase: FoCut5a target gene). The results showed that the docked molecules exhibited binding energies ranging from -31.0476 to -19.3568 kcal/mol for S. rolfsii and from -38.9474 to -26.5031 kcal/mol for F. oxysporum, highlighting the potential of these compounds as effective inhibitors. Furthermore, additional docking metrics, indicated stable interactions.
Source: Results in Chemistry
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $1,490
OpenAlex ID: W4404503675