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Synthesis of 3,3'-methylenebis(4-hydroxyquinolin-2(1H)-ones) of prospective anti-COVID-19 drugs.
Aly, Ashraf A; Hassan, Alaa A; Mohamed, Asmaa H; Osman, Esraa M; Bräse, Stefan; Nieger, Martin; Ibrahim, Mahmoud A A; Mostafa, Sara M.
  • Aly AA; Department of Chemistry, Faculty of Science, Minia University, Minia, 61519, Egypt. ashrafaly63@yahoo.com.
  • Hassan AA; Department of Chemistry, Faculty of Science, Minia University, Minia, 61519, Egypt.
  • Mohamed AH; Department of Chemistry, Faculty of Science, Minia University, Minia, 61519, Egypt.
  • Osman EM; Department of Chemistry, Faculty of Science, Minia University, Minia, 61519, Egypt.
  • Bräse S; Institute of Organic Chemistry, Karlsruhe Institute of Technology, 76131, Karlsruhe, Germany.
  • Nieger M; Institute of Biological and Chemical Systems (IBCS-FMS), Karlsruhe Institute of Technology, Eggenstein-Leopoldshafen, Germany.
  • Ibrahim MAA; Department of Chemistry, University of Helsinki, A. I. Virtasenaukio I, P.O. Box 55, 00014, Helsinki, Finland.
  • Mostafa SM; Department of Chemistry, Faculty of Science, Minia University, Minia, 61519, Egypt.
Mol Divers ; 25(1): 461-471, 2021 Feb.
Article in English | MEDLINE | ID: covidwho-756514
ABSTRACT
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.
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Full text: Available Collection: International databases Database: MEDLINE Main subject: Antiviral Agents / Protease Inhibitors / Quinolones / SARS-CoV-2 / COVID-19 Drug Treatment Type of study: Observational study / Prognostic study Limits: Humans Language: English Journal: Mol Divers Journal subject: Molecular Biology Year: 2021 Document Type: Article Affiliation country: S11030-020-10140-z

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Full text: Available Collection: International databases Database: MEDLINE Main subject: Antiviral Agents / Protease Inhibitors / Quinolones / SARS-CoV-2 / COVID-19 Drug Treatment Type of study: Observational study / Prognostic study Limits: Humans Language: English Journal: Mol Divers Journal subject: Molecular Biology Year: 2021 Document Type: Article Affiliation country: S11030-020-10140-z