Green synthesis, characterization, structure, biological activity, theoretical calculations and drug-likeness analysis of coumarins

•KF-Al2O3 efficient and reusable catalyst in a facile synthesis of coumarin derivatives.•Conventional heating and microwave irradiation in free of solvent.•Structural confirmation of the synthesized compounds was done by various spectroscopic techniques.•Drug-Likeness analysis and Geometries of synt...

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Published in:Chemical Data Collections 2020-02, Vol.25, p.100341, Article 100341
Main Authors: Khaldi-Khellafi, Nassima, Oukacha-Hikem, Djamila, Bouaziz, Souhila Terrachet, Abdoun, Amar, Makhloufi-Chebli, Malika, Dumas, Françoise, Silva, Artur M.S., Hamdi, Maamar
Format: Article
Language:English
Subjects:
Biological activity
Chemical Sciences
Coumarins
Drug-Likeness analysis
Green synthesis
Medicinal Chemistry
Microwave irradiation
Organic chemistry
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Summary:•KF-Al2O3 efficient and reusable catalyst in a facile synthesis of coumarin derivatives.•Conventional heating and microwave irradiation in free of solvent.•Structural confirmation of the synthesized compounds was done by various spectroscopic techniques.•Drug-Likeness analysis and Geometries of synthesized compounds were optimized by using B3LYP method with 6-31G* basis set.•Antioxidant and antibacterial activity. Condensation of salicylaldehydes and 2-hydroxynaphthaldehyde with various β−dicarbonyl derivatives 2a-c, in the presence of KF-Al2O3, leads to the synthesis of a series of coumarins 3-8 and benzo[f]coumarins 10 respectively by a solvent free reaction under microwave irradiation. The catalyst is recovered by a simple filtration and reused in subsequent reactions. The structure of all synthesized compounds has been established by using analytical techniques such as IR, 1H and 13C NMR spectroscopic spectra and elemental analysis. Most of the coumarins exhibited significant antibacterial activity against S. aureus Gram-positive bacteria compared to Cefotaxime as positive control. The compounds 4a and 7a demonstrated moderate antimicrobial activity against compound 8a is extremely sensitive.. In addition, the compounds showed moderate to good antiradical (DPPH) activity. Theoretical calculations let us to confirm the reaction mechanism. Parameters drug-likeness and physicochemical properties including pharmacokinetic analysis of the synthesized compounds was performed using DruliTo program. [Display omitted]
ISSN:2405-8300
2405-8300
DOI:10.1016/j.cdc.2020.100341