Synthesis of 3,3'-methylenebis(4-hydroxyquinolin-2(1H)-ones) of prospective anti-COVID-19 drugs.
Ashraf A AlyAlaa A HassanAsmaa H MohamedEsraa M OsmanStefan BräseMartin NiegerMahmoud A A IbrahimSara M MostafaPublished in: Molecular diversity (2020)
During formylation of 2-quinolones by DMF/Et3N mixture, the unexpected 3,3'-methylenebis(4-hydroxyquinolin-2(1H)-ones) were formed. The discussed mechanism was proved as due to the formation of 4-formyl-2-quinolone as intermediate. Reaction of the latter compound with the parent quinolone under the same reaction condition gave also the same product. The structure of the obtained products was elucidated via NMR, IR and mass spectra. X-ray structure analysis proved the anti-form of the obtained compounds, which were stabilized by the formation hydrogen bond. Molecular docking calculations showed that most of the synthesized compounds possessed good binding affinity to the SARS-CoV-2 main protease (Mpro) in comparable to Darunavir.
Keyphrases
- sars cov
- molecular docking
- molecular dynamics simulations
- high resolution
- density functional theory
- coronavirus disease
- respiratory syndrome coronavirus
- magnetic resonance
- molecular dynamics
- solid state
- magnetic resonance imaging
- transcription factor
- hiv infected patients
- monte carlo
- dna binding
- mass spectrometry
- electron microscopy