Synthesis, biological activities and molecular docking study of 3-(3-oxobutanoyl)-2H-chromen-2-one derivatives

Herein, we report the highly efficient total synthesis of a series of 3-(3-oxobutanoyl)-2H-chromen-2-one derivatives from salicylaldehyde(s) and 4‑hydroxy-6-methyl-2H-pyran-2-one (TAL) using Na2S2O3 as green and efficient catalyst. Structure elucidation of the products has been accomplished based on...

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Bibliographic Details
Published in:Chemical Data Collections 2021-12, Vol.36, p.100792, Article 100792
Main Authors: Benazzouz-Touami, Amina, Hikem-Oukacha, Djamila, Lamara, Kamilia Ould, Halit, Sabrina, Terrachet-Bouaziz, Souhila, Makhloufi-Chebli, Malika
Format: Article
Language:English
Subjects:
Antibacterial activity
Antioxidant activity
Coumarin
FtsZ protein
Molecular docking
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Summary:Herein, we report the highly efficient total synthesis of a series of 3-(3-oxobutanoyl)-2H-chromen-2-one derivatives from salicylaldehyde(s) and 4‑hydroxy-6-methyl-2H-pyran-2-one (TAL) using Na2S2O3 as green and efficient catalyst. Structure elucidation of the products has been accomplished based on FT-IR, mass spectroscopy, 1H NMR and 13C NMR spectroscopy. The in vitro antioxidant activities of the drugs 3-(3-oxobutanoyl)-2H-chromen-2-one were tested by the quantitative 1,1-diphenyl-2-picrylhydrazyl (DPPH.) radical scavenging activity method. The compounds 3b, 3c and 3e proved to be the most active, showing high capacity to deplete the DPPH radicals. All synthesized compounds were screened for their antimicrobial activities and the results show that only 3f was active against bacteria Staphylococcus aureus compared to antibiotic used as reference. In addition, all synthesized compounds were docked with FtsZ from S. aureus protein using AutoDock 4 software. The results suggest that 3f binds with FtsZ protein with lower energy and undergoes good interactions with the active site amino [Display omitted]
ISSN:2405-8300
2405-8300
DOI:10.1016/j.cdc.2021.100792